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
Beilstein:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2
WGK
WGK 1
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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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Alternatives to laboratory animals : ATLA, 43(2), 101-127 (2015-05-23)
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