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

Description

N-Cyano-N-phenyl-p-toluenesulfonamide, also known as N-phenyltoluenesulfonamide cyanide, is an organic compound that serves as an important intermediate in the synthesis of various chemical compounds. It is characterized by its cyano and phenyl groups attached to a toluenesulfonamide moiety, which contributes to its reactivity and utility in chemical reactions.

Uses

Used in Chemical Synthesis:
N-Cyano-N-phenyl-p-toluenesulfonamide is used as a research reactant for the synthesis of 1,2,4-triazol-3-imines through stepwise cycloaddition. This application is significant in the development of new chemical compounds with potential applications in various fields, such as pharmaceuticals, materials science, and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Cyano-N-phenyl-p-toluenesulfonamide is used as a key intermediate in the synthesis of various drug candidates. Its unique chemical structure allows for the creation of novel molecules with potential therapeutic properties, contributing to the advancement of drug discovery and development.
Used in Materials Science:
N-Cyano-N-phenyl-p-toluenesulfonamide is also utilized in the field of materials science for the development of new materials with specific properties. Its reactivity and functional groups enable the synthesis of compounds that can be used in the creation of advanced materials for various applications, such as electronics, coatings, and adhesives.

Upstream product

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

Downstream Products

• 84672-52-6 N-acetyl-N-phenyl-p-toluenesulfonamide 
• 68-34-8 phenyl toluenesulfonamide 
• 102-07-8 bis(diphenyl)urea 
• 70-55-3 toluene-4-sulfonamide 
• 64-10-8 phenyl carbamate 
• 104-15-4 toluene-4-sulfonic acid 
• 28446-70-0 (E)-4-methylcinnamonitrile 
• 2571-52-0 cyanomesitylene 
• 529-19-1 2-Methylbenzonitrile 
• 766-84-7 3-chloro-benzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 100-47-0 benzonitrile 
• 874-90-8 4-methoxybenzonitrile 
• 6609-56-9 2-methoxy-benzonitrile 

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.