55305-43-6

Basic information

• Product Name: N-Cyano-N-phenyl-p-toluenesulfonaMide
• Synonyms: N-Cyano-N-phenyl-p-toluenesulfonaMide;N-Cyano-N-phenyl-p-toluenesulphonamide;N-Cyano-4-methyl-N-phenylbenzenesulfonamide
• CAS NO: 55305-43-6
• Molecular Formula: C₁₄H₁₂N₂O₂S
• Molecular Weight: 272.32228
• Mol File: 55305-43-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 85-87 °C
• Boiling Point: 418.4±38.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -8.96±0.50(Predicted)
• CAS DataBase Reference: N-Cyano-N-phenyl-p-toluenesulfonaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyano-N-phenyl-p-toluenesulfonaMide(55305-43-6)
• EPA Substance Registry System: N-Cyano-N-phenyl-p-toluenesulfonaMide(55305-43-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 55305-43-6(Hazardous Substances Data)

Usage

Uses

N-Cyano-N-phenyl-p-toluenesulfonamide is a useful research reactant for the synthesis of synthesis of 1,?2,?4-?triazol-?3-?imines through stepwise cycloaddition.

Upstream product

• 64-10-8 phenyl carbamate 
• 104-15-4 toluene-4-sulfonic acid 
• 98-09-9 benzenesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 103-85-5 monophenylthiourea 
• 622-34-4 1-phenylcyanamide 
• 62-53-3 aniline 

Downstream Products

• 25775-03-5 2-(1H-pyrazol-1-yl)-benzonitrile 
• 1447827-19-1 C₁₀H₆⁽²⁾H₄N₂O 
• 1447827-15-7 1-benzyl-2-(1-(methoxyimino)ethyl)-1H-pyrrole-3-carbonitrile 
• 1447826-84-7 2-(1-(methoxyimino)ethyl)-5-methylbenzonitrile 
• 1447826-85-8 2-(1-(methoxyimino)ethyl)-4-methylbenzonitrile 
• 1447826-86-9 2-(1-(methoxyimino)ethyl)-3-methylbenzonitrile 
• 1447826-87-0 5-methoxy-2-(1-(methoxyimino)ethyl)benzonitrile 
• 1447826-88-1 methyl 3-cyano-4-(1-(methoxyimino)ethyl)benzoate 
• 1447826-89-2 5-fluoro-2-(1-(methoxyimino)ethyl)benzonitrile 
• 1447826-90-5 5-chloro-2-(1-(methoxyimino)ethyl)benzonitrile 
• 1447826-91-6 5-bromo-2-(1-(methoxyimino)ethyl)benzonitrile 
• 1447826-92-7 5-iodo-2-(1-(methoxyimino)ethyl)benzonitrile 
• 1447826-93-8 3-cyano-4-(1-(methoxyimino)ethyl)phenyl 4-methylbenzenesulfonate 
• 1447826-94-9 N-(3-cyano-4-(1-(methoxyimino)ethyl)phenyl)acetamide 

Relevant articles and documents

Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent

Rh(iii)-catalyzed direct vinylic C-H cyanation reaction has been developed as a practical method for the synthesis of alkenyl nitriles. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation.

A boron-nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones

Cyanation offers a simple method for the introduction of a nitrile group into organic molecules and an orthogonal route for the installation of a wide array of functional groups using simple transformations. Cyanation methods are dominated by transition metal catalysis and the use of hydrogen cyanide gas. Here, the electrophilic cyanation of enones was achieved using a main-group catalyst and a non-toxic, electrophilic cyanide source. This protocol was applied across a broad substrate scope including those containing reducible functional groups. Mechanistic studies indicated an amino-borane intermediate which underwent B-N transborylation (B-N/B-H exchange) to achieve catalytic turnover.

A practical method for N-cyanation of secondary amines and sulfonamides

Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl)-N-arylsulfonyl-cyanamides, as the significant building blocks of the organic transformation.