propargyl alcohol

General Material Information

Preferred name	propargyl alcohol
Trivial Name	Propargyl alcohol
Short Description	1-hydroxy-2-propyne
Formula	C3 H4 O
CAS Number	107-19-7
ECHA Number	203-471-2
FDA UNII	E920VF499L
Nikkaji Number	J13B
Beilstein Number	0506003
MDL	MFCD00002912
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	acetylene carbinol acetylenylcarbinol agrisynth PA ethynyl carbinol ethynylcarbinol 3-hydroxy-1-propyne 1-hydroxy-2-propyne methanol, ethynyl- prop-2-in-1-ol prop-2-yn-1-ol prop-2-yne-1-ol propargylalcohol 2-propyn-1-ol 1-propyn-3-ol 1-propyn-3-yl alcohol 3-propynol propynyl alcohol 2-propynyl alcohol 2-Propyn-1-ol 1-Propyn-3-ol 1-Hydroxy-2-propyne 3-Hydroxy-1-propyne 2-Propynol 2-Propynyl alcohol 3-Propynol 1-Propyn-3-yl alcohol Hydroxymethylacetylene NSC 8804 3-Hydroxypropyne Propiolic alcohol

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Literature & References

	prop-2-yn-1-ol
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	107-19-7
Pubchem (cid):	7859
Pubchem (sid):	134972259

Publications by PubMed
trans-Diborylation of Alkynes: pseudo-Intramolecular Strategy utilizing Propargylic Alcohol Unit.
Total Synthesis of the Biphenyl Alkaloid (-)-Lythranidine.
EGF Receptor-Targeting Peptide Conjugate Incorporating a Near-IR Fluorescent Dye and a Novel 1,4,7-Triazacyclononane-Based (64)Cu(II) Chelator Assembled via Click Chemistry.
6-Triazolyl-6-deoxy-β-cyclodextrin derivatives: synthesis, cellular toxicity, and phase-solubility study.
Construction of Divergent Fused Heterocycles via an Acid-Promoted Intramolecular ipso-Friedel-Crafts Alkylation of Phenol Derivatives.
Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity.
Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols.
First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge.
Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group.
Fluorescence sensor for Cu(II) in the serum sample based on click chemistry.
Rh(III)-catalyzed coupling of benzamides with propargyl alcohols via hydroarylation-lactonization.
Increasing the structural span of alkyne metathesis.
Evaluation of propargyl alcohol toxicity and carcinogenicity in F344/N rats and B6C3F1/N mice following whole-body inhalation exposure.
Rhodamine-propargylic esters for detection of mitochondrial hydrogen sulfide in living cells.
Lewis acid catalysis and ligand exchange in the asymmetric binaphthol-catalyzed propargylation of ketones.
Oxygenation of ruthenium carbene complexes containing naphthothiophene or naphthofuran: spectroscopic and DFT studies.
Gold meets rhodium: tandem one-pot synthesis of β-disubstituted ketones via Meyer-Schuster rearrangement and asymmetric 1,4-addition.
Benzyne cycloaddition onto carbon nanohorns.
Platinum catalysed hydrosilylation of propargylic alcohols.
New Ag(I)-iminophosphorane coordination polymers as efficient catalysts precursors for the MW-assisted Meyer-Schuster rearrangement of propargylic alcohols in water.
Lewis acid-catalyzed cyclization of enaminones with propargylic alcohols: regioselective synthesis of multisubstituted 1,2-dihydropyridines.
Trimerization of β-cyclodextrin through the click reaction.
Skeletal diversification via heteroatom linkage control: preparation of bicyclic and spirocyclic scaffolds from N-substituted homopropargyl alcohols.
A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling-isomerization-condensation reaction.
One-pot synthesis of pyrazoles through a four-step cascade sequence.
Nucleophilic ortho-propargylation of aryl sulfoxides: an interrupted Pummerer/allenyl thio-Claisen rearrangement sequence.
Hydrophosphination of propargylic alcohols and amines with phosphine boranes.
Kinetic and dynamic kinetic resolution of secondary alcohols with ionic-surfactant-coated Burkholderia cepacia lipase: substrate scope and enantioselectivity.
Atom-economical chemoselective synthesis of 1,4-enynes from terminal alkenes and propargylic alcohols catalyzed by Cu(OTf)2.
Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.
Original TDAE strategy using propargylic chloride: rapid access to 1,4-diarylbut-3-ynol derivatives.
Synthesis of novel 2-alkyl triazole-3-alkyl substituted quinoline derivatives and their cytotoxic activity.
Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition.
Synthesis of 9-alkylated calcitriol and two 1α,25-dihydroxy-9-methylene-10,19-dihydrovitamin D3 analogues with a non-natural triene system by thermal sigmatropic rearrangements.
Microwave spectroscopic and atoms in molecules theoretical investigations on the Ar···propargyl alcohol complex: Ar···H-O, Ar···π, and Ar···C interactions.
1-(2'-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis.
Synthesis of indeno[1,2-c]furans via a Pd-catalyzed bicyclization of 2-alkynyliodobenzene and propargylic alcohol.
Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution-cyclization-aromatization.
Ruthenium-catalyzed reductive coupling of 1,3-enynes and aldehydes by transfer hydrogenation: anti-diastereoselective carbonyl propargylation.
Facile synthesis of fully substituted dihydro-β-carbolines via Brønsted acid promoted cascade reactions of α-indolyl propargylic alcohols with nitrones.
Propargyl hydrazides: synthesis and conversion into pyrazoles through hydroamination.
Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.
Ruthenium-catalyzed allylation-cyclization reactions of cyclic 1,3-dicarbonyl compounds with 1-vinyl propargyl alcohols.
Hypoiodous acid initiated rearrangement of tertiary propargylic alcohols to α-iodoenones.
A novel fluorescent sensor for mutational p53 DNA sequence detection based on click chemistry.
Cobalt-mediated synthesis of the tricyclo[5.2.1.0(1,6)]decene framework in solanoeclepin A.
Regioselective catalytic hydroboration of propargylic species using Cu(I)-NHC complexes.
Scope and mechanistic analysis of the enantioselective synthesis of allenes by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and propargylic alcohols.
Regioselectivity switch: gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones.
Heteropolyacid-catalyzed direct deoxygenation of propargyl and allyl alcohols.
Sequential allenylidene/vinylidene cyclization for stereoselective construction of bicyclic carbocycles from propargyl alcohol.
Kinetic versus thermodynamic stereoselectivity in the hydrostannylation of propargylic alcohol derivatives using AIBN and Et3B as promotors.
Synthesis of α-allylated α,β-unsaturated carbonyl compounds using vanadium/palladium contemporaneous dual catalysis.
Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.
Highly regioselective synthesis of polysubstituted tetrahydroquinolines by an iodine-induced tandem cyclization reaction from propargylic alcohols and amines.
Synthesis of electronically modified Ru-based neutral 16 VE allenylidene olefin metathesis precatalysts.
A gold(I)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols.
Synthesis of a heparan sulfate mimetic library targeting FGF and VEGF via click chemistry on a monosaccharide template.
Alkyl triazole glycosides (ATGs)--a new class of bio-related surfactants.
Synthesis of 3,4-dihalogenated furan-2-(5H)-ones by electrophilic cyclization of 4-hydroxy-2-alkynoates.
Development of a method for the preparation of ruthenium indenylidene-ether olefin metathesis catalysts.
EXAFS and NRVS reveal a conformational distortion of the FeMo-cofactor in the MoFe nitrogenase propargyl alcohol complex.
1,2,3-triazole: unique ligand in promoting iron-catalyzed propargyl alcohol dehydration.
A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles.
Atom-economical synthesis of functionalized cycloalkanes via catalytic redox cycloisomerization of propargyl alcohols.
Synthesis of allene triazole through iron catalyzed regioselective addition to propargyl alcohols.
Highly chemoselective calcium-catalyzed propargylic deoxygenation.
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives.
Cyclization of aromatic propargyl alcohol with a thiophene group yielding naphthothiophene aldehyde induced by a ruthenium complex.
1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.
Kinetic resolution of secondary alcohols using amidine-based catalysts.
Synthesis of tetrasubstituted alkenes through a palladium-catalyzed domino carbopalladation/C-H-activation reaction.
Brønsted acid catalyzed asymmetric propargylation of aldehydes.
Convenient synthesis and biological evaluation of modafinil derivatives: benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters.
Toxicity of propargylic alcohols on green alga--Pseudokirchneriella subcapitata.
[Development of environmentally benign transformations via 1,3-transposition of hydroxyl group].
Lewis acid-promoted three-component reactions of propargylic alcohols with 2-butynedioates and secondary amines.
Addition of arylboronic acids to arylpropargyl alcohols en route to indenes and quinolines.
Lewis acid-catalyzed propargylic etherification and sulfanylation from alcohols in MeNO₂-H₂O.
Asymmetric synthesis and sensory evaluation of sedanenolide.
Expeditious entry to novel 2-methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-chloro-4-hydroxychromen-2-one and propargylic alcohols.
Applications of propargyl esters of amino acids in solution-phase Peptide synthesis.
Chiral propargyl alcohols via the enantioselective addition of terminal di- and triynes to aldehydes.
Intramolecular OH···π interactions in alkenols and alkynols.
Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway.
Contemporaneous dual catalysis: chemoselective cross-coupling of catalytic vanadium-allenoate and π-allylpalladium intermediates.
Tandem reaction of propargyl alcohol and N-sulfonylhydrazone: synthesis of dihydropyrazole and its utility in the preparation of 3,3-diarylacrylonitrile.
S(N)1-type reactions in the presence of water: indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes.
Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane.
Preparation of Clickable Poly(3-hydroxyalkanoate) (PHA): Application to Poly(ethylene glycol) (PEG) Graft Copolymers Synthesis.
Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity.
New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents.
Synthesis and anti-HIV-1 activity of new fluoro-HEPT analogues: an investigation on fluoro versus hydroxy substituents.
Propargyl alcohols as β-oxocarbenoid precursors for the ruthenium-catalyzed cyclopropanation of unactivated olefins by redox isomerization.
Facile oxygenation reactions of ruthenium acetylide complex containing substituted olefinic group.
Application of Mitsunobu reagents to redox isomerization of CF3-containing propargylic alcohols to (E)-α,β-enones.
A new and general one-pot synthesis of propargyl alcohols from esters.
Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.
A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature.
Palladium catalyzed bicyclization of 1,8-diiodonaphthalene and tertiary propargylic alcohols to phenalenones and their applications as fluorescent chemosensor for fluoride ions.
An atom-economical access to β-heteroarylated ketones from propargylic alcohols via tandem ruthenium/indium catalysis.
Optimization of a ligand immobilization and azide group endcapping concept via "Click-Chemistry" for the preparation of adsorbents for antibody purification.
Intramolecular Nicholas reactions in the synthesis of dibenzocycloheptanes. Synthesis of allocolchicine NSC 51046 and analogues and the formal synthesis of (-)-allocolchicine.
Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane.
Ultrasonic assisted Fischer glycosylation: generating diversity for glycochemistry.
Catalytic asymmetric synthesis of chiral propargylic alcohols for the intramolecular Pauson-Khand cycloaddition.
Scandium-catalyzed propargylation of 1,3-diketones with propargyl alcohols bearing sulfur or selenium functional groups: useful transformation to furans and pyrans.
Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.
Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles.
Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.
Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols.
Expeditious synthesis of highly substituted indolizinones via a palladium-catalyzed domino sequence.
Palladium-catalyzed [3,3]-rearrangement for the facile synthesis of allenamides.
Mitotic arrest induced by a novel family of DNA topoisomerase II inhibitors.
Diversity-oriented construction of highly substituted indolizinones.
Synthesis of polysubstituted furans based on a stepwise Sonogashira coupling of (Z)-3-iodoalk-2-en-1-ols with terminal propargylic alcohols and subsequent Au(I)- or Pd(II)-catalyzed cyclization-aromatization via elimination of H2O.
Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines.
Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth.
Photodissociation dynamics of propargyl alcohol at 212 nm: the OH production channel.
Alkyne- and 1,6-elimination- succinimidyl carbonate - terminated heterobifunctional poly(ethylene glycol) for reversible "Click" PEGylation.
A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis.
Synthesis of azide-alkyne fragments for "click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols.
Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes.
Synthesis of tetrahydropyrans from propargyl alcohols and 1,1-cyclopropanediesters: a one-pot ring-opening/Conia-ene protocol.
Preparation of Disubstituted Phenyl Propargyl Alcohols, their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers.
Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols.
Silver(I)-catalyzed dual activation of propargylic alcohol and aziridine/azetidine: triggering ring-opening and endo-selective ring-closing in a cascade.
Apparent copper(II)-accelerated azide-alkyne cycloaddition.
An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.
Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity.
Enantioselective nucleophilic addition of trimethylsilylacetylene to n-phosphinoylimines promoted by C(2)-symmetric proline-derived beta-amino alcohol.
Matching active site and substrate structures for an RNA editing reaction.
Stereospecific synthesis of beta3-amino acid derivatives from propargylic alcohols: efficient solution-phase synthesis of oligopeptides without coupling agents.
Novel carbon-carbon bond formation from propargylic alcohols and olefin toward five-membered heterocyclic rings catalyzed by AgSbF6.
Functional group compatibility. Propargyl alcohol reduction in the presence of a vinyl iodide.
Synthesis of functionalized indenes via cascade reaction of aziridines and propargyl alcohols.
A versatile route to (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines and their haloamidation reaction.
'Clicking' on the nanoscale: 1,3-dipolar cycloaddition of terminal acetylenes on azide functionalized, nanometric surface templates with nanometer resolution.
A simple and versatile re-catalyzed Meyer-Schuster rearrangement of propargylic alcohols to alpha,beta-unsaturated carbonyl compounds.
Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes.
Tandem ring-opening/closing reactions of N-Ts aziridines and aryl propargyl alcohols promoted by t-BuOK.
Platinum-catalyzed cycloisomerization reaction of 1,6-enyne coupling with rearrangement of propargylic esters.
Highly regio- and stereoselective cyclic iodoetherification of 4,5-alkadienols. An efficient preparation of 2-(1'(Z)-iodoalkenyl)tetrahydrofurans.
A novel feature of intramolecular vibrational redistribution in propargyl alcohol and propargyl amine.
First synthesis of 1-chlorovinyl allenes via palladium-catalyzed allenylation of alkynoates with propargyl alcohols.
Toxicology and carcinogenesis studies of propargyl alcohol (CAS No. 107-19-7) in F344/N rats and B6C3F1 mice (inhalation studies).
Synthesis of naphthalenyl acetate by platinum-catalyzed [1,5]-sigmatropic hydrogen shift of propargylic esters.
A DFT study on the reaction pathways for carbon-carbon bond-forming reactions between propargylic alcohols and alkenes or ketones catalyzed by thiolate-bridged diruthenium complexes.
Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization.
Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety.
Rationalizing the formation of damascenone: synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms.
An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.
Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols.
Propargylation of 1,3-dicarbonyl compounds with 1,3-diarylpropynes via oxidative cross-coupling between sp3 C-H and sp3 C-H.
Direct and stereospecific synthesis of allenes via reduction of propargylic alcohols with Cp2Zr(H)Cl.
A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.
Ruthenium/TFA-catalyzed coupling of activated secondary propargylic alcohols with cyclic 1,3-diones: furan versus pyran ring formation.
Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.
Aluminum-catalyzed asymmetric alkylations of pyridyl-substituted alkynyl ketones with dialkylzinc reagents.
Self-assembled thermoreversible gels of nonpolar liquids by racemic propargylic alcohols with fluorinated and nonfluorinated aromatic rings.
Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation.
The proposal of architecture for chemical splitting to optimize QSAR models for aquatic toxicity.
Directed diastereoselectivity in the asymmetric claisen/metathesis reaction sequence.
Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into alpha,beta-unsaturated carbonyl compounds.
Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols.
Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
Palladium-catalyzed synthesis of indene derivatives via propargylic carbonates with in situ generated organozinc compounds.
One-step synthesis of substituted dihydro- and tetrahydroisoquinolines by FeCl3.6H2O catalyzed intramolecular Friedel-Crafts reaction of benzylamino-substituted propargylic alcohols.
Zirconium-promoted epoxide rearrangement-alkynylation sequence.
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment.
Remarkable effect of N-substituent on enantioselective ruthenium-catalyzed propargylation of indoles with propargylic alcohols.
Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes.
Synthesis of spirocyclic C-arylglycosides and -ribosides by ruthenium-catalyzed cycloaddition.
Directed hydrozirconation of propargylic alcohols.
Highly efficient synthesis of functionalized indolizines and indolizinones by copper-catalyzed cycloisomerizations of propargylic pyridines.
Lewis acid catalyzed propargylation of arenes with O-propargyl trichloroacetimidates: synthesis of 1,3-diarylpropynes.
Reductive cyclization of o-nitrophenyl propargyl alcohols: facile synthesis of substituted quinolines.
Lewis acid-catalyzed conjugate addition-cyclization reactions of ethenetricarboxylates with substituted propargyl alcohols: stereoselectivity in the efficient one-pot synthesis of methylenetetrahydrofurans.
Copper(I) alkoxide-catalyzed alkynylation of trifluoromethyl ketones.
Bistrimethylsilylpropargylic ether: a versatile ambident synthon to access substituted allenyne ethers and alpha-substituted bispropargylic alcohols.
Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides.
One-pot synthesis of alpha-iodo-substituted alpha,beta-unsaturated aldehydes from propargylic alcohols.
Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers.
Chiral ruthenium-allenylidene complexes that bear a fullerene cyclopentadienyl ligand: synthesis, characterization, and remote chirality transfer.
Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.
Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.
Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones.
Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters.
Iron-catalyzed carbometalation of propargylic and homopropargylic alcohols.
A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols.
Mono- and dinuclear oxovanadium(V)calixarene complexes and their activity as oxidation catalysts.
Coupling-isomerization synthesis of chalcones.
B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.
trans-hydroalumination/alkylation: one-pot synthesis of trisubstituted allylic alcohols.
Vanadium-catalyzed addition of propargyl alcohols and imines.
Synthesis of spirocyclic C-arylribosides via cyclotrimerization.
Supramolecular assemblies of chiral propargylic alcohols.
A highly efficient preparative method of alpha-ylidene-beta-diketones via Au(III)-catalyzed acyl migration of propargylic esters.
The nicholas approach to natural product hybrids.
Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: novel methylenepyrrolidine and methylenetetrahydrofuran syntheses.
Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.
Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates.
Synthesis of a NO-releasing prodrug of rofecoxib.
[1,3]-Transfer of chirality during the Nicholas reaction in gamma-benzyloxy propargylic alcohols.
Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.
Carbon 1s excitation spectroscopy of propyne, trifluoropropyne, and propargyl alcohol.
Electron inventory, kinetic assignment (E(n)), structure, and bonding of nitrogenase turnover intermediates with C2H2 and CO.
Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols.
Reactivity of alkynes containing alpha-hydrogen atoms with a triruthenium hydrido carbonyl cluster: alkenyl versus allyl cluster derivatives.
Phototransformation of clodinafop-propargyl.
Synergistic dimetallic effects in propargylic substitution reaction catalyzed by thiolate-bridged diruthenium complex.
Highly stereoselective one-pot procedure to prepare bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes.
Ruthenium-catalyzed cycloisomerizations of diynols.
Substrate interactions with the nitrogenase active site.
Synthesis of diindeno-fused 4H-cyclopenta[def]phenanthren-4-ones and related compounds via benzannulated enediynyl propargylic alcohols.
Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines.
Antinociceptive properties of acetylenic thiophene and furan derivatives: evidence for the mechanism of action.
Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers.
Aryl annulation of cyclic ketones via a magnesium carbometalation-6-pi- electrocyclization protocol.
Meerwein-Ponndorf-Verley alkynylation of aldehydes: essential modification of aluminium alkoxides for rate acceleration and asymmetric synthesis.
Regioselectivity control in a ruthenium-catalyzed cycloisomerization of diyne-ols.
Silicon-assisted propargylic transfer to aldehydes.
Substrate interaction at an iron-sulfur face of the FeMo-cofactor during nitrogenase catalysis.
The mechanism of nitrogenase. Computed details of the site and geometry of binding of alkyne and alkene substrates and intermediates.
Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the gypsy moth, Lymantria dispar.
An organometallic intermediate during alkyne reduction by nitrogenase.
(+)-3-{(4S,5S)-5-[1,1-Dimethyl-2-(phenylthio)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}prop-2-yn-1-ol.
Localization of a catalytic intermediate bound to the FeMo-cofactor of nitrogenase.
Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: a one-pot synthesis of methylenetetrahydrofurans.
B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes.
Rhenium-catalyzed aromatic propargylation.
Coupling-isomerization-coupling sequences switched on by propargyl alcohol-enone-isomerization.
Construction of azacycles based on endo-mode cyclization of allenes.
Ru(II)-catalyzed chemo- and regioselective cyclotrimerization of three unsymmetrical alkynes through boron temporary tether. One-pot four-component coupling via cyclotrimerization/Suzuki-Miyaura coupling.
Phosphorylated 1,6-diphenyl-1,3,5-hexatriene.
Rhenium-catalyzed coupling of propargyl alcohols and allyl silanes.
Facile one-pot synthesis of photochromic pyrans.
A mechanistic dichotomy in ruthenium-catalyzed propargyl alcohol reactivity: a novel hydrative diyne cyclization.
Localization of a substrate binding site on the FeMo-cofactor in nitrogenase: trapping propargyl alcohol with an alpha-70-substituted MoFe protein.
Clotrimazole, ketoconazole, and clodinafop-propargyl as potent growth inhibitors of equine Babesia parasites during in vitro culture.
Application of selectively acylated glycosides for the alpha-galactosidase-catalyzed synthesis of disaccharides.
A Rh(I)-catalyzed cycloisomerization of homo- and bis-homopropargylic alcohols.
A mild C-O bond formation catalyzed by a rhenium-oxo complex.
Ruthenium-catalyzed alkyne-propargyl alcohol addition. An asymmetric total synthesis of (+)-alpha-kainic acid.
A mechanism for the formation of bis-glutathione conjugates of propargyl alcohol.
Characterization of propargyl bromide transformation in soil.
Total synthesis of rhizoxin D, a potent antimitotic agent from the fungus Rhizopus chinensis.
Steric control of organic transformation by a dendrimer cage: organocobalt dendrimer porphyrins as novel coenzyme B(12) mimics.
Asymmetric synthesis of anti-homopropargylic alcohols from aldehydes and chiral sulfonimidoyl substituted bis(allyl)titanium complexes through generation and elimination of novel chiral alkylidenecarbene (dimethylamino)sulfoxonium ylides.
Propargyloxycarbonyl (Poc) amino acid chlorides as efficient coupling reagents for the synthesis of 100% diastereopure peptides and resin bound tetrathiomolybdate as an effective deblocking agent for the Poc group.
Asymmetric total synthesis of 11-deoxytetrodotoxin, a naturally occurring congener.
An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols.
A Ru catalyzed divergence: oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols.
A Highly diastereoselective synthesis of (1R)-(+)-camphor-based chiral allenes and their asymmetric hydroboration-oxidation reactions.
Indenylidene complexes of ruthenium: optimized synthesis, structure elucidation, and performance as catalysts for olefin metathesis--application to the synthesis of the ADE-ring system of nakadomarin A.
Coupling of alkynylTMS derivatives with vinylic iodides. An efficient route to 1,3-enynes and dienes.
Lipase-mediated resolution of 4-TMS-3-butyn-2-ol and use of the mesylate derivatives as a precursor to a highly stereoselective chiral allenylindium reagent.
A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence.
Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes.
Disposition of propargyl alcohol in rat and mouse after intravenous, oral, dermal and inhalation exposure.
Reactions of first-row transition metal ions with propargyl alcohol in the gas phase.
Atom economy: aldol-type products by vanadium-catalyzed additions of propargyl alcohols and aldehydes.
Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D.
Cytochrome P450 2E1 metabolically activates propargyl alcohol: propiolaldehyde-induced hepatocyte cytotoxicity.
A novel 1,5-benzoheteroazepine synthesis via a one-Pot coupling-isomerization-cyclocondensation sequence
Identification of metabolites of [1,2,3-(13)C]Propargyl alcohol in mouse urine by (13)C NMR and mass spectrometry and comparison to rat.
A novel three-component one-pot pyrimidine synthesis based upon a coupling-isomerization sequence.
Mechanism-based inactivation of thymidylate synthase by 5-(3-fluoropropyn-1-yl)-2'-deoxyuridine 5'-phosphate.
Identification of metabolites of [1,2,3-(13)C]Propargyl alcohol in rat urine by (13)C NMR and mass spectrometry.
Unusual propargylic oxidations catalyzed by chloroperoxidase.
Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds.
Hybrid molecules containing propargylic sulfones and DNA minor groove-binding lexitropsins: synthesis, sequence specificity of reaction with DNA and biological evaluation.
Comparative oxidation of 2-propyn-1-ol with other low molecular weight unsaturated and saturated primary alcohols by bovine liver catalase in vitro.
Mutagenic activity of 3 industrial chemicals in a battery of in vitro and in vivo tests.
Vinylstannylated alkylating agents as prosthetic groups for radioiodination of small molecules: design, synthesis, and application to iodoallyl analogues of spiperone and diprenorphine.
Zinc-activated alcohols in ternary complexes of liver alcohol dehydrogenase.
Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3 alpha-hydroxysteroid dehydrogenase.
Fluorinated androgens and progestins: molecular probes for androgen and progesterone receptors with potential use in positron emission tomography.
Flavin-dependent alcohol oxidase from yeast. Studies on the catalytic mechanism and inactivation during turnover.
Role of propiolaldehyde and other metabolites in the pargyline inhibition of rat liver aldehyde dehydrogenase.
Two geometrical isomers of linoleic acid: improved total syntheses.
Acute oral toxicity as LD50 (mg/kg) of propargyl alcohol to male and female rats.
Penitricin, a new class of antibiotic produced by Penicillium aculeatum. III. Structural confirmation by chemical synthesis and biological activity.
Sex pheromone of the European grapevine moth,Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity.
Irreversible inactivation of the flavoenzyme alcohol, oxidase with acetylenic alcohols.
Inhibition of aldehyde dehydrogenase by propiolaldehyde, a possible metabolite of pargyline.
An approach to the synthesis of C18 tri-insaturated fatty acids.
C-nucleoside studies. Part 6. Synthesis of 3-[2,3,5-tri-O-benzyl-beta-(and alpha)-D-ribofuranosyl]prop-2-yn-1-ol and related compounds; a new synthesis of 3(5)-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole.
[Synthesis of sulfazine from propargyl alcohol].

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
Metabolomics Database:	Search
KEGG (GenomeNet):	C05986
HMDB (The Human Metabolome Database):	Search
YMDB (Yeast Metabolome Database):	YMDB01377
Export Tariff Code:	2905.29.9000
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: •grade: technical; 75% solution. •97% min. activity grade

Suppliers

BASF	Sigma-Aldrich: Aldrich
TCI AMERICA

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	56.064079284668
Specific gravity	@ 25 °C
Pounds per Gallon
Vapor Pressure	10.556 mmHg @ 25 °C
Flash Point TCC Value	36.11 °C TCC
logP (o/w)	-0.38
Solubility
water, 9.355e+005 mg/L @ 25 °C (est)	Yes

Organoleptic Properties

Odor Type: Floral
geranium
General comment	At 100.00 %. geranium

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-guinea pig LD50 60 mg/kg The Threshold Limit Values Vol. 4, Pg. 346, 1980. oral-mammal (species unspecified) LD50 50 mg/kg Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988. unreported-mammal (species unspecified) LD50 53 mg/kg Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986. oral-mouse LD50 50 mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BLOOD: HEMORRHAGE Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 8, Pg. 97, 1966. oral-rat LD50 20 mg/kg "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4672, 1982.
Dermal Toxicity:
skin-rabbit LD50 16 mg/kg SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4672, 1982. subcutaneous-rabbit LDLo 25 mg/kg "Zur Pharmakologie Ungesattigter Alkohole, Dissertation," Bock, H., Pharmakologischen Institu der Universitat Breslau, Poland, 1930Vol. -, Pg. -, 1930.
Inhalation Toxicity:
inhalation-mammal (species unspecified) LC50 3000 mg/m3 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988. inhalation-mouse LC50 2000 mg/m3/2H BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 8, Pg. 97, 1966. inhalation-rat LC50 873 ppm/2H GAF Material Safety Data Sheet.

Safety in use information

Category:
herbicides / pesticides
Recommendation for propargyl alcohol usage levels up to:
	not for fragrance use.

Recommendation for propargyl alcohol flavor usage levels up to:
	not for flavor use.