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136441

Sigma-Aldrich

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
Beilstein:
774261
EC Number:
203-597-8
MDL number:
MFCD00008460
UNSPSC Code:
12352100
PubChem Substance ID:
24848281
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

200

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
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

WGK

WGK 1

Flash Point(F)

185.0 °F

Flash Point(C)

85 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
M Coker et al.
Journal of inherited metabolic disease, 19(6), 743-751 (1996-01-01)
Total plasma odd-numbered long-chain fatty acids were analysed in patients with methylmalonic acidaemia (vitamin B12-responsive and unresponsive), combined methylmalonic acidaemia/homocystinuria (CblC), propionic acidaemia (both neonatal-onset and late-onset), biotinidase deficiency and holocarboxylase synthase deficiency, as well as in hospital controls. Total
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
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