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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.)

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

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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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)
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)
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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