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126136

Diethyl methylmalonate

Name: Diethyl methylmalonate
Brand: ALDRICH

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24847702

EC Number:

210-175-7

Beilstein/REAXYS Number:

637028

MDL number:

MFCD00009162

Assay:

99%

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Properties

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

Description

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

10 - Combustible liquids

wgk

WGK 3

flash_point_f

179.6 °F - closed cup

flash_point_c

82 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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)

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)

An erythromycin process improvement using the diethyl methylmalonate-responsive (Dmr) phenotype of the Saccharopolyspora erythraea mutB strain.

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)

Global Trade Item Number

SKU	GTIN
1623580-1ML	04061842433940
525286-4L	04061838128300
525286-250ML	04061838128294
525286-20L	04061838120168
126136-500G	04061837368264
126136-100G	04061838723864