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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:
590-90-9
Molecular Weight:
88.11
EC Number:
209-693-6
MDL number:
MFCD00059005
UNSPSC Code:
12352100
PubChem Substance ID:
24855219
NACRES:
NA.22

$171.95

List Price$181.00Save 5%
Web-Only Promotion

Available to ship onApril 22, 2025Details

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Quality Level

100

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.)

functional group

hydroxyl
ketone

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.[1]

4-Hydroxy-2-butanone is an important pharmaceutical intermediate[2]. Gas phase reaction of the OH radicals with 4-hydroxy-2-butanone has been investigated by absolute rate method[3].

Application

4-Hydroxy-2-butanone has been used in the synthesis of:
  • 3-buten-2-one via dehydration over anatase-TiO2 catalyst[4]
  • 4-methyl-5-hydroxymethylthiazole[5]
  • (±)-lineatin[6]
  • mevalonic acid lactone[7][8]
  • verrucarin[9]
  • β-hydroxylactones[10]

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

91.4 °F - closed cup

flash_point_c

33 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV9489
MKCT1793
MKCS4824
MKCP6064
MKCL8587

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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
Journal of the American Chemical Society, 67, 400-400 (1945)
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)
The Journal of Organic Chemistry, 47, 929-929 (1982)
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)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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