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108421

Sigma-Aldrich

Methyl cyanoacetate

99%

Synonyme(s) :

Methyl 2-cyanoacetate

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About This Item

Formule linéaire :
NCCH2COOCH3
Numéro CAS:
105-34-0
Poids moléculaire :
99.09
Beilstein:
773945
Numéro CE :
203-288-8
Numéro MDL:
MFCD00001939
Code UNSPSC :
12352100
eCl@ss :
39031513
ID de substance PubChem :
24846667
Nomenclature NACRES :
NA.22

54,20 €

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Densité de vapeur

3.41 (vs air)

Niveau de qualité

200

Pression de vapeur

0.2 mmHg ( 20 °C)

Essai

99%

Indice de réfraction

n20/D 1.417 (lit.)

pb

204-207 °C (lit.)

Pf

−13 °C (lit.)

Densité

1.123 g/mL at 25 °C (lit.)

Groupe fonctionnel

ester
nitrile

Chaîne SMILES 

COC(=O)CC#N

InChI

1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3

Clé InChI

ANGDWNBGPBMQHW-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture[1]. It undergoes calcite or fluorite catalyzed Knövenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α-cyanocinnamic esters[2].

Application

Methyl cyanoacetate may be used in the synthesis of various 1,2,5-tricarbonyl compounds[3].

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

230.0 °F - closed cup

Point d'éclair (°C)

110 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF2549V
WXBD7921V
BCBN1608V
BCBL0892V
BCBG9316V

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MALONAMIC ACID

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Sigma-Aldrich

M1407

Malononitrile

Conformational isomerism in methyl cyanoacetate: A combined matrix-isolation infrared spectroscopy and molecular orbital study.
Reva ID, et al
Physical Chemistry Chemical Physics, 3(19), 4235-4241 (2011)
Construction of 1, 2, 5-Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper (I) Iodide-Catalyzed Aerobic Oxidation.
Kim SH, et al.
Advanced Synthesis & Catalysis, 353(18), 3335-3339 (2011)
Calcite and fluorite as catalyst for the Knovenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions.
Wada S and Suzuki H.
Tetrahedron Letters, 44(2), 399-401 (2003)
Søren S Donau et al.
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Questions

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

    1 réponse

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

    1 réponse

    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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