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Sigma-Aldrich

Diethyl methylmalonate

99%

Synonym(s):

Methylmalonic acid diethyl ester

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About This Item

Linear Formula:
CH3CH(COOC2H5)2
CAS Number:
609-08-5
Molecular Weight:
174.19
Beilstein:
637028
EC Number:
210-175-7
MDL number:
MFCD00009162
UNSPSC Code:
12352100
PubChem Substance ID:
24847702
NACRES:
NA.22

Quality Level

200

Assay

99%

refractive index

n20/D 1.413 (lit.)

bp

198-199 °C (lit.)
78-80 °C/10 mmHg

density

1.022 g/mL at 20 °C (lit.)

SMILES string

CCOC(=O)C(C)C(=O)OCC

InChI

1S/C8H14O4/c1-4-11-7(9)6(3)8(10)12-5-2/h6H,4-5H2,1-3H3

InChI key

UPQZOUHVTJNGFK-UHFFFAOYSA-N

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General description

Diethyl methylmalonate reacts with 2-cyclohexenone under abnormal Michael conditions form 2-(3-oxocyclohexyl)-2-cyclohexenone. It causes the alkylation of poly(chloromethylstyrene) during pahse transfer catalysis.

Application

Diethyl methylmalonate was used to investigate the effect of direct supplementation of the medium with di-ester of methylmalonate on erythromycin fermentation in Saccharopolyspora erythraea mutB strain.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °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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Abnormal Michael reaction. Reaction between 2-cyclohexenone and diethyl methylmalonate.
Risinger GE and Haag WG.
The Journal of Organic Chemistry, 38(20), 3546-3647 (1973)
J Mark Weber et al.
Applied microbiology and biotechnology, 93(4), 1575-1583 (2011-11-04)
The Saccharopolyspora erythraea mutB knockout strain, FL2281, having a block in the methylmalonyl-CoA mutase reaction, was found to carry a diethyl methylmalonate-responsive (Dmr) phenotype in an oil-based fermentation medium. The Dmr phenotype confers the ability to increase erythromycin A (erythromycin)
Alkylation reaction of poly (chloromethylstyrene) with malononitrile and diethyl methylmalonate using phase transfer catalysts.
Nishikubo T, et al.
Makromol. Chem., 2(6-7), 387-392 (1981)

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