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108421

Sigma-Aldrich

Methyl cyanoacetate

99%

Synonym(s):

Methyl 2-cyanoacetate

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About This Item

Linear Formula:
NCCH2COOCH3
CAS Number:
Molecular Weight:
99.09
Beilstein/REAXYS Number:
773945
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39031513
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.41 (vs air)

Quality Level

vapor pressure

0.2 mmHg ( 20 °C)

assay

99%

refractive index

n20/D 1.417 (lit.)

bp

204-207 °C (lit.)

mp

−13 °C (lit.)

density

1.123 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC#N

InChI

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

InChI key

ANGDWNBGPBMQHW-UHFFFAOYSA-N

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General description

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

Application

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

wgk_germany

WGK 1

ppe

Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

C88602

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MALONAMIC ACID AldrichCPR

S937436

MALONAMIC ACID

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Sigma-Aldrich

M1407

Malononitrile

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)
Conformational isomerism in methyl cyanoacetate: A combined matrix-isolation infrared spectroscopy and molecular orbital study.
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