108421
Methyl cyanoacetate
99%
Synonym(s):
Methyl 2-cyanoacetate
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About This Item
Linear Formula:
NCCH2COOCH3
CAS Number:
Molecular Weight:
99.09
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
39031513
UNSPSC Code:
12352100
EC Number:
203-288-8
MDL number:
Beilstein/REAXYS Number:
773945
Assay:
99%
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.)
functional group
ester, nitrile
SMILES string
COC(=O)CC#N
InChI
1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3
InChI key
ANGDWNBGPBMQHW-UHFFFAOYSA-N
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves
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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.
Reva ID, et al
Physical Chemistry Chemical Physics, 3(19), 4235-4241 (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)