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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:
105-34-0
Molecular Weight:
99.09
Beilstein/REAXYS Number:
773945
EC Number:
203-288-8
MDL number:
MFCD00001939
UNSPSC Code:
12352100
eCl@ss:
39031513
PubChem Substance ID:
24846667
NACRES:
NA.22

vapor density

3.41 (vs air)

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
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

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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Cyanoacetohydrazide 98%

Sigma-Aldrich

C88602

Cyanoacetohydrazide

MALONAMIC ACID AldrichCPR

S937436

MALONAMIC ACID

Malononitrile ≥99%

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)
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