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Merck
CN

136441

Dimethyl malonate

98%

Synonym(s):

Dimethyl propanedioate, Malonic acid dimethyl ester

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About This Item

Linear Formula:
CH2(COOCH3)2
CAS Number:
108-59-8
Molecular Weight:
132.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848281
EC Number:
203-597-8
Beilstein/REAXYS Number:
774261
MDL number:
MFCD00008460
Assay:
98%
Form:
liquid

Key Documents

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Product Name

Dimethyl malonate, 98%

InChI key

BEPAFCGSDWSTEL-UHFFFAOYSA-N

InChI

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

SMILES string

COC(=O)CC(=O)OC

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.)

functional group

ester

Quality Level

200

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Application

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

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3971
STBK8123
STBK5148
STBJ4888
STBJ0276

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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
Jeroen S Dickschat et al.
Chembiochem : a European journal of chemical biology, 5(6), 778-787 (2004-06-03)
The volatiles emitted from cell cultures of myxobacterium Myxococcus xanthus were collected by use of a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Two new natural products, (S)-9-methyldecan-3-ol ((S)-1) and 9-methyldecan-3-one (2), were identified and synthesized, together with other
Shinji Kato
Journal of the American Chemical Society, 127(33), 11538-11539 (2005-08-18)
Layer-by-layer (LbL) assembly of triarylamine (TAA)-containing polymers has been applied for anode functionalizations in organic light-emitting diodes (OLEDs). Surface work function of the ITO electrodes was significantly altered with the functionalizations, and the values changed depending on electron affinity of
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