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252557

Sigma-Aldrich

4-Hydroxy-2-butanone

95%

Synonym(s):

2-Hydroxyethyl methyl ketone

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About This Item

Linear Formula:
HOCH2CH2COCH3
CAS Number:
Molecular Weight:
88.11
EC Number:
MDL number:
UNSPSC Code:
12352100
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 a beta-hydroxy ketone used as a starting material to synthesize 1,3-butanediol.

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

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the American Chemical Society, 79, 2316-2316 (1957)
Recent advances in fermentative production of C4 diols and their chemo-catalytic upgrading to high-value chemicals
Varma AR, et al.
Chinese Journal of Catalysis, 52, 99-126 (2023)
Synthesis of 3-buten-2-one from 4-hydroxy-2-butanone over anatase-TiO2 catalyst.
Ichikawa N, et al.
Catalysis Communications, 6(1), 19-22 (2005)
The Journal of Organic Chemistry, 47, 929-929 (1982)
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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