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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
form:
liquid
Assay:
98%
Pricing and availability is not currently available.

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[1].

Application

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3971
STBK8123
STBK5148
STBJ4888
STBJ0276

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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)
B A McLaughlin et al.
Journal of neurochemistry, 70(6), 2406-2415 (1998-05-29)
Intrastriatal injections of the mitochondrial toxins malonate and 3-nitropropionic acid produce selective cell death similar to that seen in transient ischemia and Huntington's disease. The extent of cell death can be attenuated by pharmacological or surgical blockade of cortical glutamatergic
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
Violeta Iosub et al.
The Journal of organic chemistry, 75(5), 1612-1619 (2010-02-06)
A convenient and versatile enantioselective synthesis of biologically important alpha-quaternary amino acid derivatives was based on the sequential double alkylation or arylation of dimethyl malonate, followed by desymmetrization with porcine liver esterase (PLE) and Curtius rearrangement. The PLE-mediated hydrolysis of
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Questions

1–3 of 3 Questions  

  1. A-t-il été conditionné en condition stérile ?

    1 answer

    1. This is not considered a sterile product. It is not filtered sterilized or packaged under sterile conditions.

      Helpful?

  2. Est-il possible de réaliser des injections de DMM avec du PBS 1X ?

    1 answer

    1. This product is not tested for suitability for in vitro or in vivo applications. The product is not sterile and endotoxin levels are not determined, however the minimum purity is 98%. There is a product option available with a higher purity specification. Product 8.00899, while also not tested for in vivo use, has a minimum purity of 99%. Please see the link below to review this product:
      https://www.sigmaaldrich.com/product/mm/800899

      Helpful?

  3. Bonjour, J'aimerai avoir quelques indications sur cet inhibiteur ( DMM ( 136441 )) Dans quel solvant est resuspendu le DMM ? A quel concentration ? ( 1 g/mL ? )

    1 answer

    1. This product is a neat or pure liquid. The melting point is -62 deg. C. The molecular weight is 132.11 and the density is 1.156g/mL. The calculated molarity is 8.75M. Per the product page, solubility information is as follows:
      alcohol: miscible
      diethyl ether: miscible
      oil: miscible
      water: slightly soluble

      Helpful?

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