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380067

Sigma-Aldrich

4,4-Dimethoxy-2-butanone

technical grade, ≥90%

Synonym(s):

3-Oxobutyraldehyde dimethylacetal, 3-Ketobutyraldehyde dimethyl acetal, 4,4-Dimethoxy-2-butanone, Acetylacetaldehyde dimethylacetal

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About This Item

Linear Formula:
CH3COCH2CH(OCH3)2
CAS Number:
5436-21-5
Molecular Weight:
132.16
Beilstein:
1702372
EC Number:
226-605-1
MDL number:
MFCD00008789
UNSPSC Code:
12352100
PubChem Substance ID:
24863716
NACRES:
NA.22

grade

technical grade

Assay

≥90%

form

liquid

refractive index

n20/D 1.414 (lit.)

bp

70-73 °C/20 mmHg (lit.)

density

0.996 g/mL at 25 °C (lit.)

SMILES string

COC(CC(C)=O)OC

InChI

1S/C6H12O3/c1-5(7)4-6(8-2)9-3/h6H,4H2,1-3H3

InChI key

PJCCSZUMZMCWSX-UHFFFAOYSA-N

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General description

4,4-Dimethoxy-2-butanone (Acetylacetaldehyde dimethylacetal) is a ketone.

Application

4,4-Dimethoxy-2-butanone (β-ketobutyracetal) may be used in the preparation of:
  • (R)-4,4-dimethoxy-2-butanol
  • pyrazoles and pyrimidines
  • [7,16-dihydro- 6,15( 17)-dimetbyldibenzo[b,i]-[1,4,8,11]tetrilazacyclotetradecinato-N5,N9,N14,N18]nickel{II)
4,4-Dimethoxy-2-butanone (Acetylacetaldehyde dimethylacetal) may be used in the preparation of N,N-diethyl-[2-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]-pyrimidin-3-yl]acetamide and acetoacetaldehyde.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

134.6 °F - closed cup

Flash Point(C)

57 °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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Olga B Gutiérrez Acosta et al.
Applied and environmental microbiology, 79(20), 6228-6235 (2013-08-06)
Acetone is activated by aerobic and nitrate-reducing bacteria via an ATP-dependent carboxylation reaction to form acetoacetate as the first reaction product. In the activation of acetone by sulfate-reducing bacteria, acetoacetate has not been found to be an intermediate. Here, we
Yamadazyma Farinosa IFO 10896-mediated reduction of 4, 4-dimethoxy-2-butanone as the key-step for the preparation of 1, 3-diols with unsymmetrical substituents.
Yamazaki T, et al.
Synthetic Communications, 30(16), 3061-3072 (2000)
β-keto acetals. I. Synthesis of pyrazoles and pyrimidines and the steric inhibition of resonance in 5-alkyl-1-p-nitrophenylpyrazoles.
Burness DM.
The Journal of Organic Chemistry, 21(1), 97-101 (1956)
2-Arylpyrazolo [1,5-a] pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands.
Selleri S, et al.
BioTechnology: An Indian Journal, 9(10), 2661-2671 (2001)
Facile template synthesis of nickel (II) complexes of dibenzotetraaza [14] annulenes.
Cutler AR, et al.
Inorganic Chemistry, 24(14), 2276-2281 (1985)

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