126136
Diethyl methylmalonate
99%
Synonym(s):
Methylmalonic acid diethyl ester
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About This Item
Linear Formula:
CH3CH(COOC2H5)2
CAS Number:
Molecular Weight:
174.19
Beilstein:
637028
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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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)
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)
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)
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