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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:
774261
Número CE:
203-597-8
Número MDL:
MFCD00008460
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24848281
NACRES:
NA.22
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densidad de vapor

>1 (vs air)

Nivel de calidad

200

Ensayo

98%

Formulario

liquid

índice de refracción

n20/D 1.413 (lit.)

bp

180-181 °C (lit.)

mp

−62 °C (lit.)

solubilidad

alcohol: miscible
diethyl ether: miscible
oil: miscible
water: slightly soluble

densidad

1.156 g/mL at 25 °C (lit.)

grupo funcional

ester

cadena SMILES

COC(=O)CC(=O)OC

InChI

1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3

Clave InChI

BEPAFCGSDWSTEL-UHFFFAOYSA-N

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Descripción general

Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines[1].

Aplicación

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

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H319

Clasificaciones de peligro

Eye Irrit. 2

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

185.0 °F - closed cup

Punto de inflamabilidad (°C)

85 °C - closed cup

Equipo de protección personal

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (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)
Oxidation of glycerol and propanediols in methanol over heterogeneous gold catalysts.
Taarning E, et al.
Green Chemistry, 10(4), 408-414 (2008)
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
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
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
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Questions

1–5 of 5 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. 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.

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  4. 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?

  5. 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

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