68029-41-4

Basic information

• Product Name: 3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide
• CAS NO: 68029-41-4
• Molecular Formula: C₁₀H₇ClN₂S
• Molecular Weight: 222.694
• Mol File: 68029-41-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 389.8°C at 760 mmHg
• Flash Point: 189.5°C
• Density: 1.385g/cm³
• Vapor Pressure: 2.77E-06mmHg at 25°C
• Refractive Index: 1.701
• CAS DataBase Reference: 3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide(68029-41-4)
• EPA Substance Registry System: 3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide(68029-41-4)

Safety Data

• Hazardous Substances Data: 68029-41-4(Hazardous Substances Data)

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 127118-60-9 2,6-diamino-4-(2-chlorophenyl)-4H-thiopyran-3,5-dicarbonitrile 
• 864546-63-4 4-(2-chloro-phenyl)-5-cyano-2-methyl-6-thioxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 
• 347363-71-7 2-allylthio-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thienoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine 
• 1450734-15-2 (E)-3-(2-chlorophenyl)-2-cyano-1-iminioprop-2-ene-1-sulfenate 

Relevant articles and documents

1-(Cyanoacetyl)-3,5-dimethylpyrazole as active methylene compound in hantzsch-type pyridine synthesis: A convenient and highly effective approach to 3,5-dicyano-4-(het)aryl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates

Reaction of 1-(cyanoacetyl)-3,5-dimethylpyrazole with (E)-2-cyano-3-(het) arylprop-2-enethioamides was used for the synthesis of N-methylmorpholinium 3,5-dicyano-4-(het)aryl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates for the first time. The latter were also obtained in a multicomponent one-pot mode via the condensation of cyanothioacetamide with corresponding aldehydes and above 1-cyanoacetylpyrazole in the presence of N-methylmorpholine under mild conditions. Thiolates 1 exist as a pair of cis/trans-diastereomers in different ratios (from 3:4 to 2:1). Springer-Verlag 2007.

Synthesis, structure, and electrochemical characteristics of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles

We have obtained 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4- dihydropyridine-3-carboxylic acid nitriles by S-alkylation of the corresponding 2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxylic acid nitrile by iodoacetamide or one-pot multicomponent synthesis methods: condensation of 2-arylidene-acetoacetic acid ethyl ester, 2-cyanothioacetamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, 3-aryl-2-cyanothioacrylamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, an aromatic aldehyde, 2-cyanothioacetamide, piperidine, and iodoacetamide. We have carried out a comparative analysis of the capability of 2-alkylthio-4-aryl-5- ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles for electrochemical oxidation as a function of the electronic properties of the aryl substituent in the 4 position of the heterocycle and the 2-alkylthio substituent. X-ray diffraction data indicate the existence of a hydrogen bond between the C=O of the 2-carbamoylmethylthio substituent and the NH of the hydrogenated heterocycle, which explains the more facile oxidation of the studied compounds compared with 2-methylthio-substituted 1,4-dihydropyridines.