1192690-93-9

Basic information

• Product Name: 3-aMino-1H-Indole-2-carbonitrile
• Synonyms: 3-aMino-1H-Indole-2-carbonitrile
• CAS NO: 1192690-93-9
• Molecular Formula: C₉H₇N₃
• Molecular Weight: 157.17198
• Mol File: 1192690-93-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-aMino-1H-Indole-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-aMino-1H-Indole-2-carbonitrile(1192690-93-9)
• EPA Substance Registry System: 3-aMino-1H-Indole-2-carbonitrile(1192690-93-9)

Safety Data

• Hazardous Substances Data: 1192690-93-9(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 174969-51-8 N-(2-cyanophenyl)cyanothioformamide 
• 1242952-11-9 2-(cyanomethyleneamino)benzonitrile 
• 74897-46-4 3-amino-1-(p-tosyl)indole-2-carbonitrile 

Downstream Products

• 1192691-07-8 (2-cyanoindol-3-yl)iminotriphenylphosphorane 
• 1227096-71-0 3-(benzenesulfonylamino)indole-2-carbonitrile 
• 1227096-68-5 3-(p-tosylamino)indole-2-carbonitrile 
• 1383659-91-3 N'-(1-benzyl-2-cyano-1H-indol-3-yl)-N,N-dimethylformimidamide 

Relevant articles and documents

The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2- carbonitriles using triphenylphosphine

2-Cyano cyanothioformanilide 3a reacts with triphenylphosphine in the presence of water to give 2-(cyanomethyleneamino)benzonitrile 4a, 2-(cyanomethylamino)benzonitrile 5, 3-aminoindole-2-carbonitrile 2a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 6a. In the presence of p-toluenesulfonic acid in MeOH the reaction between 2-cyano cyanothioformanilide 3a and triphenylphosphine (2 equiv) gives 3-aminoindole-2-carbonitrile 2a in 90% yield. Under the same conditions 2-(cyanomethyleneamino)benzonitrile 4a gives anthranilonitrile 8a, 3-aminoindole-2-carbonitrile 2a and N-(2-cyanophenyl)formamide 9. In addition, substituted 2-cyano cyanothioformanilides 3b-f react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b-f in 63-75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2- carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 3g, (2-cyano-5,6- dimethoxyindol-3-yl)iminotriphenylphosphorane 6g and 2-(cyanomethyleneamino)-4, 5-dimethoxybenzonitrile 4g are obtained. The structure of 2- (cyanomethyleneamino)-4,5-dimethoxybenzonitrile 4g is supported unambiguously via independent synthesis and comparison to the isomeric 6,7- dimethoxyquinazoline-2-carbonitrile 15. All new compounds are fully characterised and a tentative mechanism for the transformation of 2-cyano cyanothioformanilides to indoles is proposed.

The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine

2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog