85565-07-7

Basic information

• Product Name: N,N-diisopropyl-4-methylbenzenesulfinamide
• Synonyms: N,N-diisopropyl-4-methylbenzenesulfinamide
• CAS NO: 85565-07-7
• Molecular Weight: 239.382
• Mol File: 85565-07-7.mol

Chemical Properties

• CAS DataBase Reference: N,N-diisopropyl-4-methylbenzenesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-diisopropyl-4-methylbenzenesulfinamide(85565-07-7)
• EPA Substance Registry System: N,N-diisopropyl-4-methylbenzenesulfinamide(85565-07-7)

Safety Data

• Hazardous Substances Data: 85565-07-7(Hazardous Substances Data)

Upstream product

• 4111-54-0 lithium diisopropyl amide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 108-18-9 diisopropylamine 

Downstream Products

• 64396-66-3 methyl (R)-4-methylbenzenesulfinate 
• 59203-01-9 (S)-(+)-1-methyl 4-methylbenzenesulfinate 
• 112458-71-6 ethyl (R)-4-methylbenzenesulfinate 
• 59203-02-0 (R)-ethyl p-toluenesulfinate 
• 422509-92-0 4-Methyl-benzenesulfinic acid (S)-propyl ester 
• 70003-95-1 isopropyl (R)-4-methylbenzenesulfinate 
• 59203-03-1 (R)-isopropyl p-toluenesulfinate 

Relevant articles and documents

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.

Asymmetric Synthesis of 2H-Azirine 2-Carboxylate Esters

2H-Azirine 2-carboxylate esters (5), the smallest unsaturated nitrogen heterocycle, are readily prepared in enantiomerically pure form via the base-induced elimination of sulfenic acid (RSOH) from nonracemic N-sulfinylaziridine 2-carboxylate esters (4). Optimum yields were obtained when the aziridine was treated with TMSCl at -95 °C followed by LDA, which was attributed to the improved leaving group ability of an silicon-oxonium species. By using this new methodology the first asymmetric syntheses of the marine cytotoxic antibiotics (R)-(-)- and (S)-(+)-dysidazirine (2) were accomplished.