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(S)-(+)-2-butanol

Chemical Structure

General Material Information

Preferred name (S)-(+)-2-butanol
Trivial Name (+)-2-Butanol
Short Description (S)-()-sec-butyl alcohol
Formula C4 H10 O
CAS Number 4221-99-2
ECHA Number 224-168-1
FDA UNII 69KXU5NDTO
Nikkaji Number J9.275D
Beilstein Number 1718763
MDL MFCD00064281
NMR Predictor External link
Synonyms
  • (2S)- butan-2-ol
  • (2S)-(+)- butan-2-ol
  • (S)- butan-2-ol
  • (2S)-2-butanol
  • (S)-()-2-butanol
  • (S)-2-butanol
  • 2-butanol, (2S)-
  • 2-butanol, (S)-
  • (S)-()-sec- butyl alcohol
  • D-(+)- ethylmethylcarbinol
  • 2-Butanol, (2S)-
  • sec-Butyl alcohol, (S)-(+)-
  • 2-Butanol, (S)-
  • (+)-2-Butanol
  • (S)-2-Butanol
  • L-2-Butanol
  • d-Butanol
  • (S)-sec-Butanol
  • (S)-sec-Butyl alcohol
  • (2S)-2-Butanol
  • (S)-(+)-sec-Butanol
  • (1S)-1-Methylpropan-1-ol
  • (S)-(-)-2-Butanol

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Literature & References

Leffingwell:Chirality or Article
(2S)-butan-2-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):444683
Pubchem (sid):135230769
Publications by PubMed
Enantioselective, continuous (R)- and (S)-2-butanol synthesis: Achieving high space-time yields with recombinant E. coli cells in a micro-aqueous, solvent-free reaction system.
The effect of fluorine substitution on chiral recognition: interplay of CH···π, OH···π and CH···F interactions in gas-phase complexes of 1-aryl-1-ethanol with butan-2-ol.
Age-dependent changes in the ratio of (R)- and (S)-2-butanol released by virgin females of Dasylepida ishigakiensis (Coleoptera: Scarabaeidae).
Intermolecular chiral assemblies in R(-) and S(+) 2-butanol detected by microcalorimetry measurements.
Mixed-valent uranium(IV,VI) diphosphonate: synthesis, structure, and spectroscopy.
Enzyme-based glucose delivery as a high content screening tool in yeast-based whole-cell biocatalysis.
Mating disruption by a synthetic sex pheromone in the white grub beetle Dasylepida ishigakiensis (Coleoptera: Scarabaeidae) in the laboratory and sugarcane fields.
Kinetic resolution of (R,S)-2-butanol using enzymatic synthesis of esters.
Chiral recognition between 1-(4-fluorophenyl)ethanol and 2-butanol: higher binding energy of homochiral complexes in the gas phase.
Immobilization conditions of ketoreductase on enantioselective reduction in a gas-solid bioreactor.
Molecular basis for enantioselectivity in the (R)- and (S)-hydroxypropylthioethanesulfonate dehydrogenases, a unique pair of stereoselective short-chain dehydrogenases/reductases involved in aliphatic epoxide carboxylation.
Enantioselective HF loss promoted by resonant two-photon ionization of supersonically expanded (R)-1-phenyl-2,2,2-trifluoroethanol clusters.
Compound-specific nitrogen isotope analysis of D-alanine, L-alanine, and valine: application of diastereomer separation to delta15N and microbial peptidoglycan studies.
Chiral-selective chemistry induced by spin-polarized secondary electrons from a magnetic substrate.
Enantioselective chemisorption of propylene oxide on a 2-butanol modified Pd(111) surface: the role of hydrogen-bonding interactions.
A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase mutant derivative highly active and stereoselective on phenylacetone and benzylacetone.
Gas-phase chiral separations by ion mobility spectrometry.
Chirality in anesthesia I: minimum alveolar concentration of secondary alcohol enantiomers.
Modelling neurotransmitter functions: a laser spectroscopic study of (1S,2S)-N-methyl pseudoephedrine and its complexes with achiral and chiral molecules.
Analysis of vibrational circular dichroism spectra of (s)-(+)-2-butanol by rotational strengths expressed in local symmetry coordinates.
The stereoselectivity and catalytic properties of Xanthobacter autotrophicus 2-[(R)-2-Hydroxypropylthio]ethanesulfonate dehydrogenase are controlled by interactions between C-terminal arginine residues and the sulfonate of coenzyme M.
Enantioseparation of chiral amino acids as the N(O,S)-ethoxycarbonylated diastereomeric esters by achiral dual-capillary column gas chromatography.
R2PI Study of intermolecular hydrogen bond in solvent-free chiral complexes.
Spectroscopic studies of enantiomeric discrimination in jet-cooled chiral complexes.
Short-range interactions within molecular complexes formed in supersonic beams: structural effects and chiral discrimination
Stereospecificity of hydrogen transfer by the NAD(+)-linked alcohol dehydrogenase from the Antarctic psychrophile Moraxella sp. TAE123.
Kinetic mechanism of yeast alcohol dehydrogenase activity with secondary alcohols and ketones.
Assay of the enantiomers of 1,2-propanediol, 1,3-butanediol, 1,3-pentanediol, and the corresponding hydroxyacids by gas chromatography-mass spectrometry.
An improved procedure for the analysis of linkage positions in 2-acetamido-2-deoxy-D-glucopyranosyl residues by the reductive-cleavage method.
Analysis by the reductive-cleavage method of a polysaccharide containing 2-acetamido-2,6-dideoxy-D- and -L-galactopyranosyl residues.
Substrate specificity and stereoselectivity of horse liver alcohol dehydrogenase. Kinetic evaluation of binding and activation parameters controlling the catalytic cycles of unbranched, acyclic secondary alcohols and ketones as substrates of the native and active-site-specific Co(II)-substituted enzyme.
Determination of alpha-alkyl-alpha-amino acids and alpha-amino alcohols by chiral-phase capillary gas chromatography and reverse-phase high-performance liquid chromatography.
Occurrence of multiple forms of alcohol dehydrogenase in Penicillium supplemented with 2,3-butanediol.

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
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2905.14.5050
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 74.122901916504
Specific gravity @ 20 °C
Pounds per Gallon 6.723 to 6.748
Refractive Index 1.396 to 1.398 @ 20 °C
Boiling Point 96 to 97°C @ 760 mm Hg
Vapor Pressure 25.243999 mmHg @ 25 °C
Flash Point TCC Value 26.7 °C TCC
logP (o/w) 0.691 est
Solubility
alcohol Yes
water, 1.304e+005 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Oily
oily, winey
General comment At 1.00 % in dipropylene glycol. oily wine

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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
natural substances and extractives
Recommendation for (S)-(+)-2-butanol usage levels up to:
not for fragrance use.
Recommendation for (S)-(+)-2-butanol flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :444683
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(2S)-butan-2-ol
Chemidplus:0004221992
RTECS:EO1750000 for cas# 4221-99-2