132431-15-3

Basic information

• Product Name: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile
• Synonyms: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile
• CAS NO: 132431-15-3
• Molecular Weight: 254.356
• Mol File: 132431-15-3.mol

Chemical Properties

• CAS DataBase Reference: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile(132431-15-3)
• EPA Substance Registry System: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile(132431-15-3)

Safety Data

• Hazardous Substances Data: 132431-15-3(Hazardous Substances Data)

Upstream product

• 93-61-8 N-methyl-N-phenylformamide 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 132431-18-6 (E)-7-iodo-2-(N-methylanilino)hept-2-enenitrile 
• 132431-21-1 (2E,4E)-2-(Methyl-phenyl-amino)-5-phenyl-penta-2,4-dienenitrile 
• 101383-73-7 (2Z,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile 
• 101383-72-6 (2E,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile 
• 69567-06-2 (N-methylanilino)prop-2-enenitrile 
• 86803-42-1 (E)-2-(N-Methylanilino)-2-hexenenitrile 
• 145968-99-6 (2E,5E)-4-(2-bromobenzyl)-2-(N-methylanilino)-6-phenylthiohexa-2,5-dienenitrile 
• 1485-19-4 9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 132431-20-0 (E)-2-(methyl(phenyl)amino)penta-2,4-dienenitrile 
• 99839-93-7 N-methyl-N-phenyl-carbamoyl cyanide 
• 40936-70-7 S-phenyl N-methyl-N-phenylcarbamothioate 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 3295-92-9 N-methyl N-phenyl carbamate d'isopropyle 
• 2621-79-6 ethyl N-methyl-N-phenylcarbamate 

Relevant articles and documents

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.

2-(N-Methylanilino)-2-phenylthioacetonitrile: a Useful Reagent for Preparation of Conjugated α-Amino Alkenenitriles via Tandem Alkylation and Dehydrosulphenylation

Alkylation of the anion of 2-(N-methylanilino)-2-phenylthioacetonitrile 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Counterattack by bromide and benzenethiolate ion