667-14-1

Basic information

• Product Name: N-benzoyl-p-toluene sulfonimidoyl chloride
• Synonyms: N-benzoyl-p-toluene sulfonimidoyl chloride
• CAS NO: 667-14-1
• Molecular Weight: 293.774
• Mol File: 667-14-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-benzoyl-p-toluene sulfonimidoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzoyl-p-toluene sulfonimidoyl chloride(667-14-1)
• EPA Substance Registry System: N-benzoyl-p-toluene sulfonimidoyl chloride(667-14-1)

Safety Data

• Hazardous Substances Data: 667-14-1(Hazardous Substances Data)

Upstream product

• 657-84-1 sodium tosylate 
• 93-97-0 benzoic acid anhydride 
• 6873-55-8 p-tolylsulfinyl amide 
• 18513-02-5 N-(4-tolylsulfinyl)-benzamide 

Downstream Products

• 1221253-15-1 N-benzoyl-4-toluenesulfonimide-N'-cyclohexylamide 
• 1264737-57-6 N-benzoyl-4-methylphenyl sulfonimidoyl fluoride 
• 1264737-70-3 N-[oxo(p-tolyl)(trifluoromethyl)-λ6-sulfanylidene]benzamide 
• 3406-18-6 C₂₀H₁₇NO₃S 

Relevant articles and documents

Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism

SuFEx reactions, in which an S?F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, “Si-free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.

Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.