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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.)

functional group

ester

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

136441-250ML:
136441-VAR:
136441-250G:
136441-1L:
136441-BULK:
136441-1KG:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3971
STBK8123
STBK5148
STBJ4888
STBJ0276

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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)
Ingalill Andersson et al.
The clinical respiratory journal, 1(1), 23-29 (2007-07-01)
Eating problems are common in patients with chronic obstructive pulmonary disease (COPD), and intake of micronutrients might be lower than recommended. To study dietary intake, serum and urinary concentration of trace elements and vitamins in elderly underweight patients with established
Luiz Fernando Freire Royes et al.
Pharmacology, biochemistry, and behavior, 83(1), 136-144 (2006-02-14)
Methylmalonic acidemias are metabolic disorders caused by a severe deficiency of methylmalonyl CoA mutase activity, which are characterized by neurological dysfunction, including convulsions. It has been reported that methylmalonic acid (MMA) accumulation inhibits succinate dehydrogenase (SDH) and beta-hydroxybutyrate dehydrogenase activity
Paul R Blakemore et al.
Organic letters, 7(21), 4721-4724 (2005-10-08)
[reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate.
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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