17865-14-4

Basic information

• Product Name: Benzenesulfonamide, N-(trimethylsilyl)-
• CAS NO: 17865-14-4
• Molecular Formula: C9H15NO2SSi
• Molecular Weight: 229.375
• Mol File: 17865-14-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(trimethylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(trimethylsilyl)-(17865-14-4)
• EPA Substance Registry System: Benzenesulfonamide, N-(trimethylsilyl)-(17865-14-4)

Safety Data

• Hazardous Substances Data: 17865-14-4(Hazardous Substances Data)

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 98-10-2 benzenesulfonamide 
• 75-77-4 chloro-trimethyl-silane 
• 16513-17-0 methyltrimethylsilylamine 

Downstream Products

• 60199-41-9 N-phenylsulfonyl-2,4-dinitrobenzenesulfenamide 
• 745019-99-2 C₃₆H₃₂N₄O₇S 
• 745019-86-7 C₂₈H₂₉N₃O₅S 
• 138815-40-4 2,2,2-trifluoroethyl-N-trimethylsilyl Benzenesulfonimidate 
• 138815-41-5 Phenyl N-trimethylsilyl Benzenesulfonimidate 
• 60199-40-8 N-phenylsulfonylpentachlorobenzenesulfenamide 
• 3559-04-4 N-benzoyl-benzenesulfonamide 
• 138937-41-4 N-Trimethylsilylbenzenesulfonimidoyl Chloride 
• 34609-07-9 N-(2-Oxo-pyrrolidin-1-ylmethyl)-benzenesulfonamide 
• 5219-80-7 N,N'-bis(benzenesulfonyl)urea 
• 54459-38-0 C₁₉H₁₇N₃O₇S₃ 

Relevant articles and documents

Synthesis, characterization, and theoretical analysis of soluble poly(oxothiazenes): The ambient temperature lewis acid catalyzed in situ polymerization of N-silylsulfonimidoyl chlorides

The ambient temperature condensation, to yield low molecular weight poly(methyloxothiazene) (Mw = 1 × 104; PDI = 1.4), can be achieved by the reaction of MeS(O2)NHSiMe3 and SOCl2 - this latter reactio

Novel synthesis of sulfonimidoyl halides and sulfonimidates from N-Silylated sulfonamides and dihalophosphoranes

In the past, general methods for the preparation of sulfonimidoyl chlorides have involved oxidation of sulfur-(IV) compounds with various oxidizing agents. For the purpose of studying the thermal decomposition of suitably substituted sulfonimidates to sulfur-nitrogen based polymeric materials, a simple method was developed for the synthesis of sulfonimidoyl halides from readily available sulfur(VI) starting materials. Unsubstituted sulfonamides are known to react with Ph3P-CCl4 to produce only N-phosphoranylidenesulfonamides. In contrast, we have found that the reaction of N-silylated sulfonamides [RSO2NHSiMe3 (6), RSO2N(SiMe3)2 (7)] with Ph3PCl2 in CHCl3 yields N-trimethylsilylsulfonimidoyl chlorides, Me3SiN=S(O)(R)Cl, 11, except when the group R is strongly electronegative, like CF3. Further, the reaction of 7 (R = Me) with Ph3PBr2 in CH2Cl2 produced the first detectible sulfonimidoyl bromide, Me3SiN=S(O)(Me)Br, 12. The sulfonimidoyl chlorides 11 were converted (in one-pot reactions) to 2,2,2-trifluoroethyl-, phenyl-, or ethyl N-trimethylsilylsulfonimidates 3 (R = Me, Et, ClCH32CH2CH2, PhCH=CH, Ph, 4-F-C6H4). In preliminary reactions, it was found that the N-silylsulfonimidates can in turn be derivatized by taking advantage of the susceptibility of the Si-N bond to cleavage.

Catalysts for Silylations with 1,1,1,3,3,3-Hexamethyldisilazane

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