252557

Sigma-Aldrich

4-Hydroxy-2-butanone

95%

Synonym(s):
2-Hydroxyethyl methyl ketone
Linear Formula:
HOCH2CH2COCH3
CAS Number:
Molecular Weight:
88.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

refractive index

n20/D 1.430 (lit.)

bp

73-76 °C/12 mmHg (lit.)

density

1.023 g/mL at 25 °C (lit.)

SMILES string

CC(=O)CCO

InChI

1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3

InChI key

LVSQXDHWDCMMRJ-UHFFFAOYSA-N

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General description

4-Hydroxy-2-butanone is an important pharmaceutical intermediate. Gas phase reaction of the OH radicals with 4-hydroxy-2-butanone has been investigated by absolute rate method.

Application

4-Hydroxy-2-butanone has been used in the synthesis of:
  • 3-buten-2-one via dehydration over anatase-TiO2 catalyst
  • 4-methyl-5-hydroxymethylthiazole
  • (±)-lineatin
  • mevalonic acid lactone
  • verrucarin
  • β-hydroxylactones

Packaging

100 g in glass bottle

Pictograms

Flame

Signal Word

Warning

Hazard Statements

hazcat

Flam. Liq. 3

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Studies on the biosynthesis of cholesterol. 5. Biosynthesis of squalene from DL-3-hydroxy-3-methyl [2-14C] pentano-5-lactone.
J W CORNFORTH et al.
The Biochemical journal, 69(1), 146-155 (1958-05-01)
Journal of the American Chemical Society, 104, 5486-5486 (1982)
Hon Wai Lam et al.
Organic letters, 7(19), 4225-4228 (2005-09-09)
[reaction: see text] Copper bisphosphine complexes catalyze the intramolecular reductive aldol reaction of alpha,beta-unsaturated esters with ketones, affording five- and six-membered beta-hydroxylactones in high stereoselectivities. Utilization of chiral nonracemic bisphosphines render the cyclizations enantioselective.
Journal of the American Chemical Society, 67, 400-400 (1945)
Gisèle El Dib et al.
The journal of physical chemistry. A, 117(1), 117-125 (2012-12-06)
The reaction of the OH radicals with 4-hydroxy-2-butanone was investigated in the gas phase using an absolute rate method at room temperature and over the pressure range 10-330 Torr in He and air as diluent gases. The rate coefficients were...

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