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136441

Sigma-Aldrich

Dimethyl malonate

98%

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Synonym(s):
Dimethyl propanedioate, Malonic acid dimethyl ester
Linear Formula:
CH2(COOCH3)2
CAS Number:
Molecular Weight:
132.11
Beilstein:
774261
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.413 (lit.)

bp

180-181 °C (lit.)

mp

−62 °C (lit.)

solubility

alcohol: miscible
diethyl ether: miscible
oil: miscible
water: slightly soluble

density

1.156 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC(=O)OC

InChI

1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3

InChI key

BEPAFCGSDWSTEL-UHFFFAOYSA-N

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This Item
D97754W2375078.00899
Dimethyl malonate 98%

Sigma-Aldrich

136441

Dimethyl malonate

Diethyl malonate ReagentPlus®, 99%

Sigma-Aldrich

D97754

Diethyl malonate

Diethyl malonate ≥98%, FG

Sigma-Aldrich

W237507

Diethyl malonate

Dimethyl malonate for synthesis

Sigma-Aldrich

8.00899

Dimethyl malonate

form

liquid

form

liquid

form

-

form

liquid

refractive index

n20/D 1.413 (lit.)

refractive index

n20/D 1.413 (lit.)

refractive index

n20/D 1.413 (lit.)

refractive index

-

bp

180-181 °C (lit.)

bp

199 °C (lit.)

bp

199 °C (lit.)

bp

181-183 °C/1013 hPa

mp

−62 °C (lit.)

mp

−51-−50 °C (lit.)

mp

−51-−50 °C (lit.)

mp

-61.9 °C

solubility

alcohol: miscible, diethyl ether: miscible, oil: miscible, water: slightly soluble

solubility

-

solubility

-

solubility

-

General description

Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.

Application

Dimethyl malonate was used in gold catalyzed oxidative esterification of glycerol, 1,2-propanediol and 1,3-propanediol.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Chiral thienylpyridines as N-S ligands for asymmetric catalysis: Palladium-catalyzed allylic alkylation and copper-catalyzed cyclopropanation reactions.
Chelucci G, et al.
J. Mol. Catal. A: Chem., 197(1), 27-35 (2003)
Oxidation of glycerol and propanediols in methanol over heterogeneous gold catalysts.
Taarning E, et al.
Green Chemistry, 10(4), 408-414 (2008)
B A McLaughlin et al.
Journal of neurochemistry, 70(6), 2406-2415 (1998-05-29)
Intrastriatal injections of the mitochondrial toxins malonate and 3-nitropropionic acid produce selective cell death similar to that seen in transient ischemia and Huntington's disease. The extent of cell death can be attenuated by pharmacological or surgical blockade of cortical glutamatergic
Violeta Iosub et al.
The Journal of organic chemistry, 75(5), 1612-1619 (2010-02-06)
A convenient and versatile enantioselective synthesis of biologically important alpha-quaternary amino acid derivatives was based on the sequential double alkylation or arylation of dimethyl malonate, followed by desymmetrization with porcine liver esterase (PLE) and Curtius rearrangement. The PLE-mediated hydrolysis of
R Padmakumar et al.
Analytical biochemistry, 214(1), 318-320 (1993-10-01)
A rapid and high-yield synthesis of methylmalonyl coenzyme A is reported. The two-step procedure involves preparation of the thiophenyl ester of methylmalonic acid using dicyclohexylcarbodiimide as a condensing agent, followed by transesterification with coenzyme A, to yield methylmalonyl coenzyme A

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