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

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

Downstream Products

• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 40491-79-0 butyl 4-methylbenzenesulfinate 
• 40491-80-3 octyl 4-methylbenzenesulfinate 
• 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 
• 102-97-6 Benzyl-isopropyl-amin 
• 1020731-54-7 N-benzyl-N-diphenylphosphanyl-p-tolylsulfinamide borane 
• 93938-07-9 N-benzyl-p-toluenesulfonimidomorpholide 
• 138711-78-1 C₁₉H₂₃NOS 
• 138711-66-7 C₁₇H₁₉NOS 
• 123552-96-5 C₁₆H₁₉NOS 
• 103-67-3 benzyl-methyl-amine 

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.

Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides

An unexpected time-controlled highly selective C3-or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.