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296171

Sigma-Aldrich

Methyl 4-acetyl-5-oxohexanoate

98%

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About This Item

Linear Formula:
(CH3CO)2CHCH2CH2CO2CH3
CAS Number:
13984-53-7
Molecular Weight:
186.21
MDL number:
MFCD00008760
UNSPSC Code:
12352100
PubChem Substance ID:
24857842
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.459 (lit.)

bp

182 °C/48 mmHg (lit.)

density

1.066 g/mL at 25 °C (lit.)

functional group

ester
ketone

SMILES string

COC(=O)CCC(C(C)=O)C(C)=O

InChI

1S/C9H14O4/c1-6(10)8(7(2)11)4-5-9(12)13-3/h8H,4-5H2,1-3H3

InChI key

XFUDNZLAPUHONL-UHFFFAOYSA-N

Application

Methyl 4-acetyl-5-oxohexanoate is a β-ketoester, has been used:
  • in modified Knorr condensation for the synthesis of pyrrole
  • to identify the Michael addition product by using GC and GC-MS
  • in preparation of dibenzyl-3,6-dimethylpyrazine-2,5-dicarboxylate

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000142058
0000094493
0000089435
15118TH
00610KH

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Suppressed native hydrolytic activity of a lipase to reveal promiscuous Michael addition activity in water.
Svedendahl M, et al.
ChemCatChem, 1(2), 252-258 (2009)
C-H??? p and C= O??? p Intermolecular Interactions in Dibenzyl-3, 6-dimethylpyrazine-2, 5-dicarboxylate.
Silva JA, et al.
Journal of Chemical Crystallography, 38(4), 301-303 (2008)
Mechanism of a modified Knorr pyrrole condensation.
Rapoport H and Harbuct JW.
The Journal of Organic Chemistry, 36(6), 853-855 (1971)

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