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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:
108-59-8
Peso molecular:
132.11
Beilstein/REAXYS Number:
774261
EC Number:
203-597-8
MDL number:
MFCD00008460
UNSPSC Code:
12352100
PubChem Substance ID:
24848281
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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Categorías relacionadas

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_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)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

112402

Succinato de dietilo

Malonic acid anhydrous, free-flowing, Redi-Dri™, ReagentPlus®, 99%

Sigma-Aldrich

792535

Malonic acid

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
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
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