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N-(2-Cyanoethyl)-N-methylaniline

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CAS:94-34-8
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CAS:94-34-8
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CAS:94-34-8
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CAS:94-34-8
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CAS: 94-34-8
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N-(2-Cyanoethyl)-N-methylaniline Basic information
Product Name:N-(2-Cyanoethyl)-N-methylaniline
Synonyms:3-(methylphenylamino)-propanenitril;N-Methyl-N-Cyanoethyl Aniline;3-(METHYLPHENYLAMINO)PROPIONITRILE 97%;N-(2-CYANOETHYL)-N-METHYLANILINE / 3-(METHYLPHENYLAMINO)PROPIONITRILE;3-(N-Methyl-N-phenylamino)propiononitrile;3-(N-methylanilino)propanenitrile;N-Methyl-N-(2-cyanoethyl)aniline 3-(N-Methyl-N-phenylamino)propionitrile;3-(N-METHYLANILINO)PROPIONITRILE
CAS:94-34-8
MF:C10H12N2
MW:160.22
EINECS:202-325-5
Product Categories:aniline derivatives;Intermediates of Dyes and Pigments
Mol File:94-34-8.mol
N-(2-Cyanoethyl)-N-methylaniline Structure
N-(2-Cyanoethyl)-N-methylaniline Chemical Properties
Boiling point 313 °C(lit.)
density 1.035 g/mL at 25 °C(lit.)
refractive index n20/D 1.56(lit.)
Fp 125-127°C/4mm
storage temp. Inert atmosphere,Room Temperature
form clear liquid
pka4.54±0.50(Predicted)
color White to Yellow to Green
Specific Gravity1.05
BRN 2803416
CAS DataBase Reference94-34-8(CAS DataBase Reference)
EPA Substance Registry SystemPropanenitrile, 3-(methylphenylamino)- (94-34-8)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38-21/22
Safety Statements 26-36-36/37
WGK Germany 3
TSCA TSCA listed
PackingGroup III
HS Code 29214300
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
N-(2-Cyanoethyl)-N-methylaniline Usage And Synthesis
SynthesisAn activated carbon-supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 mol percent) was added to a 10 mL Schlenk tube; after the evacuation of argon, add 1 mL of solvent (toluene). Under argon protection, to the above system, Were successively added phenylsilane (78.9 mg, 0.75 mmol), 3-Anilinopropionitrile (43.9 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol). The whole anti-reaction was carried out at 80 ° C with stirring for 15 hours. After completion of the reaction, 3 mL of ethyl acetate was added to the system. The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL). Ethyl acetate (3 x 10 mL), the organic phase was separated, Dried over anhydrous Na2SO4, and filtered; the solvent was removed by rotary evaporation. The residue was purified by column chromatography on ethyl acetate/petroleum ether = 1: 50 mixed solvent. Separation and purification gave N-(2-Cyanoethyl)-N-methyl aniline 226.4 mg, yield of 55 per cent.
References[1] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10375 - 10379
[2] Tetrahedron, 2013, vol. 69, # 6, p. 1712 - 1716
[3] Green Chemistry, 2010, vol. 12, # 5, p. 786 - 789
[4] Synthesis, 2008, # 24, p. 3931 - 3936
[5] Journal of the American Chemical Society, 1944, vol. 66, p. 725,728
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