6873-90-1

Basic information

• Product Name: Benzenesulfinamide, 4-methyl-N-(phenylmethyl)-
• CAS NO: 6873-90-1
• Molecular Formula: C14H15NOS
• Molecular Weight: 245.345
• Mol File: 6873-90-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzenesulfinamide, 4-methyl-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfinamide, 4-methyl-N-(phenylmethyl)-(6873-90-1)
• EPA Substance Registry System: Benzenesulfinamide, 4-methyl-N-(phenylmethyl)-(6873-90-1)

Safety Data

• Hazardous Substances Data: 6873-90-1(Hazardous Substances Data)

Upstream product

• 1858-86-2 Ethyl p-toluenesulfinate 
• 100-46-9 benzylamine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 6873-55-8 p-tolylsulfinyl amide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1365659-60-4 C₁₄H₁₅NS 
• 672-78-6 methyl p-toluene sulfinate 
• 536-57-2 p-toluene sulfinic acid 
• 10439-23-3 4-methylbenzenesulfinyl chloride 

Downstream Products

• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 91796-57-5 4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 123552-90-9 C₁₄H₁₄ClNOS 
• 13146-13-9 benzyl 4-methylbenzenesulfinate 
• 40491-79-0 butyl 4-methylbenzenesulfinate 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 1020731-54-7 N-benzyl-N-diphenylphosphanyl-p-tolylsulfinamide borane 
• 102-97-6 Benzyl-isopropyl-amin 
• 780-25-6 N-benzylidene benzylamine 
• 100-52-7 benzaldehyde 
• 1351958-49-0 (Rs)-N-benzyl-4-methylbenzenesulfinamide 
• 169330-83-0 (S)-N-benzyl-4-methylbenzenesulfinamide 
• 138711-78-1 C₁₉H₂₃NOS 
• 138711-66-7 C₁₇H₁₉NOS 

Relevant articles and documents

Synthetic preparation of N-alkyl and N-aryl arenesulfinamides using an arenesulfinic acid-CDI driven approach

A new synthetic methodology has been developed for the synthesis of N-alkyl and N-aryl arenesulfinamides. The methodology involved reacting arenesulfinic acids (R = -Me, -H, -Cl) with 1,1’-carbonyldiimidazole (CDI) to form the reactive intermediate, an arenesulfinylimidazole. This intermediate was then reacted with both primary and secondary amines to yield the corresponding N-alkyl sulfinamides in yields up to 90%. While the overall yields ranged from 52% to 90%, the level of diastereoselection with racemic or enantiomerically enriched amines only reached a level of 54:46 favoring the major diastereomer as determined by analysis of the 500 MHz 1H NMR spectra. A series of aniline derivatives were also investigated as coupling partners and were found to form the N-aryl arenesulfinamide in good yield.

Kinetic Resolution of Sulfinamides via Asymmetric N-Allylic Alkylation

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.

Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides

It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry.