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Merck

136441

Sigma-Aldrich

Dimethyl malonate

98%

Sinónimos:

Dimethyl propanedioate, Malonic acid dimethyl ester

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About This Item

Fórmula lineal:
CH2(COOCH3)2
Número de CAS:
Peso molecular:
132.11
Beilstein/REAXYS Number:
774261
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

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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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

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificados de análisis (COA)

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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)
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
Lawrence P Tardibono et al.
Organic letters, 11(18), 4076-4079 (2009-08-22)
Homoallylic esters are obtained in a single transformation from allyl 2,2,2-trifluoroethyl malonates by using a Pd(0) catalyst. Facile decarboxylation of allyl 2,2,2-trifluoroethyl malonates is attributed to a decrease in pK(a) compared to allyl methyl malonates. Subsequent reduction of the homoallylic
G B MacPhee et al.
Archives of disease in childhood, 69(4), 433-436 (1993-10-01)
Two new cases of malonyl coenzyme A (CoA) decarboxylase deficiency are described. Hitherto, the worldwide experience of the disorder has been confined to reports on two affected Australian children. The new cases are Scots born and are the offspring of

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