2901-92-0

Basic information

• Product Name: Benzenesulfinyl chloride, 4-chloro-
• CAS NO: 2901-92-0
• Molecular Formula: C6H4Cl2OS
• Molecular Weight: 195.069
• Mol File: 2901-92-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenesulfinyl chloride, 4-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfinyl chloride, 4-chloro-(2901-92-0)
• EPA Substance Registry System: Benzenesulfinyl chloride, 4-chloro-(2901-92-0)

Safety Data

• Hazardous Substances Data: 2901-92-0(Hazardous Substances Data)

Upstream product

• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 106-54-7 p-Chlorothiophenol 
• 353243-81-9 4-chlorophenyl 2-(trimethylsilyl)ethyl sulfide 
• 108-90-7 chlorobenzene 
• 19378-58-6 N-(4-chloro-phenylsulfanylmethyl)-phthalimide 
• 143505-43-5 (2-((4- chlorophenyl)sulfinyl)ethyl)trimethylsilane 
• 100-03-8 4-chlorobenzenesulfinic acid 

Downstream Products

• 111531-31-8 4-chloro-benzenesulfinic acid benzhydryl ester 
• 79248-64-9 (S)-1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose p-chlorobenzenesulfinate 
• 79248-64-9 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose p-chlorobenzenesulfinate 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 154345-70-7 [(4-Chloro-benzenesulfinyl)-phenyl-methylene]-triphenyl-λ⁵-phosphane 
• 21502-37-4 N-Triphenylphosphoranyliden-4-chlor-benzolsulfinsaeureamid 
• 708-66-7 p-chlorophenyl trifluoromethyl sulfoxide 
• 169216-73-3 4-(4-Chloro-benzenesulfinyl)-2,3,5,6-tetramethyl-phenol 
• 1104591-43-6 N-[(4-chlorophenyl)sulfinyl]-2,6-di-tert-butyl-1,4-benzoquinone imine 
• 1104591-49-2 N-[(4-chlorophenyl)sulfinyl]-2,6-dichloro-1,4-benzoquinone imine 
• 75626-38-9 N-<(p-chlorophenyl)thio>-1,4-benzoquinone 4-imine S-oxide 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 77198-05-1 C₁₉H₁₄Cl₂N₂OS 
• 41231-46-3 benzyl 4-chlorobenzenesulfinate 

Relevant articles and documents

Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions

Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is

Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature

The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.

Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)- arylsulfinamides

A novel and simple process for the preparation of enantiomerically pure (SS)-benzenesulfinamide (SS)-3a, (SS)-p- toluenesulfinamide (SS)-3b, (SS)-p-chloro- benzenesulfinamide (SS)-3c and (SS)-p- fluorobenzenesulfinamide (SS)-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)- arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,SS)-N-benzyl-N-(1-phenylethyl)- arylsulfinamides (R,SS)-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,SS)-1 were then converted into four enantiopure (RS)-methyl arylsulfinates (RS)-2, and finally into four enantiopure (SS)- arylsulfinamides (SS)-3 in good yields.

Toward a synthetically useful stereoselective C-H amination of hydrocarbons

Reaction between a sulfur(VI) compound and an iodine(III) oxidant in the presence of a catalytic quantity (≤3 mol %) of a rhodium(II) catalyst leads to the formation of a chiral metallanitrene of unprecedented reactivity. The latter allows intermolecular C-H amination to proceed in very high yields up to 92% and excellent diastereoselectivities up to 99% with C-H bond containing starting materials as the limiting component. The scope of this C-H functionalization includes benzylic and allylic substrates as well as alkanes. Secondary positions react preferentially, but insertion into activated primary C-H bonds or sterically accessible tertiary sites is also possible. Cooperative effects between the nitrene precursor and the chiral catalyst at the origin of these good results have also been applied to kinetic resolution of racemic sulfonimidamide. This methodology paves the way to the use of Csp3-H bonds as synthetic precursors for the introduction of a nitrogen functionality into selected positions.

Convenient method for the preparation of aryl sulfinyl chlorides

Reaction of activated arenes with thionyl chloride in the presence of montmorillonite K-10 clay affords the corresponding aryl sulfinyl chlorides in good yield.

Oxidative fragmentations of 2-(trimethylsilyl)ethyl sulfoxides - Routes to alkane-, arene-, and highly substituted 1-alkenesulfinyl chlorides

The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is suitable for most alkane- and arenesulfinyl chlorides (3), but is limited to highly substituted vinylic sulfinyl chlorides. 1-Alkenyl 2-(trimethylsilyl)ethyl sulfoxides with reduced double bond substitution (6, 7, 11) succumb to reactions involving chlorination of the double bond. The β-effect of silicon is invoked to explain the ability of the 2-(trimethylsilyl)ethyl group to induce C-S bond scission under the oxidative cleavage reaction conditions. A mechanism is offered to account for the role played by the β-silicon atom of the 2-(trimethylsilyl)ethyl group. Indeed, the silicon atom is self-sacrificial in that it diverts the course of the reaction from the usual α-carbon chlorination mode to one of oxidative cleavage, whereby the 2-(trimethylsilyl)ethyl group is lost. The overall reaction calls upon the ability of silicon atoms to donate electron density by hyperconjugation.

Nitrosations with hydrazine derivatives: Synthesis of N4-arenesulfinylsemicarbazides and N5-arenesulfinyl-N1-aminobiuretes from arenesulfinylisocyanates and N,N-disubstituted hydrazines

Arenesulfinyl-isocyanates 5 prepared in situ from arenesulfinyl chlorides 4 and silver cyanate react with N,N-disubstituted hydrazines to mixtures of N4-arenesulfinylsemicarbazides 6 as main components and N5-arenesulfinyl-N1/s

Sulfonimidamides

This invention provides certain sulfonimidamide compounds, formulations and method of use of these compounds in treating susceptible neoplasms.

The reaction of 2-trimethylsilylethyl sulfoxides with sulfuryl chloride. A fragmentation route to sulfinyl chlorides

Sulfinyl chlorides were prepared in good to excellent yields by reacting aryl or alkyl 2-trimethylsilylethyl sulfoxides with SO2Cl2.

Convenient methods for the preparation of sulfur substituted allenecarboxylates

2-Sulfinyl- and 2-sulfonylallenecarboxylates, as new 1,1-diacceptor substituted allenes, were prepared starting from methyl 4-hydroxy-4-methyl-2-pentynoate by a [2,3]-sigmatropic rearrangement. The sulfoxides could be reduced to the corresponding allenyl sulfides. A 2(5H)-furanone derivative was prepared by a side-reaction.