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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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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

Quality Level

200

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

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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
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)
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 Y Choi et al.
Proceedings of the National Academy of Sciences of the United States of America, 87(8), 3174-3176 (1990-04-01)
To probe for free radical intermediates in the model methylmalonate to succinate rearrangements promoted by vitamin B12s, a model series with a pentenyl side chain radical trap has been devised. The control free radical, generated by tri-n-butyltin hydride treatment of
Catalytic oxidative decarboxylation of malic acid into dimethyl malonate in methanol with dioxygen.
Junxia Liu et al.
ChemSusChem, 5(11), 2151-2154 (2012-10-12)
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