41719-05-5

Basic information

• Product Name: Benzenemethanesulfinyl chloride
• CAS NO: 41719-05-5
• Molecular Formula: C7H7ClOS
• Molecular Weight: 174.651
• Mol File: 41719-05-5.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanesulfinyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanesulfinyl chloride(41719-05-5)
• EPA Substance Registry System: Benzenemethanesulfinyl chloride(41719-05-5)

Safety Data

• Hazardous Substances Data: 41719-05-5(Hazardous Substances Data)

Upstream product

• 150-60-7 dibenzyl disulphide 
• 52096-57-8 2-(Benzylthiomethyl)-1H-isoindole-1,3(2H)-dione 
• 100-53-8 phenylmethanethiol 
• 10113-29-8 tetrabenzyltin 
• 7719-09-7 thionyl chloride 
• 16302-98-0 petivericin 
• 18053-55-9 benzyl 2-(trimethylsilyl)ethyl sulfide 
• 143505-47-9 benzyl 2-(trimethylsilyl)ethyl sulfoxide 

Downstream Products

• 24824-97-3 Benzyl-α-chlormethyl-sulfoxid 
• 41719-10-2 Iodmethyl-benzyl-sulfoxid 
• 19158-29-3 4-(6-phenylmethanesulfinyl-cyclohex-1-enyl)-morpholine 
• 42300-72-1 Aethyl-α-toluolsulfinat 
• 1198104-88-9 C₁₁H₁₅BrO₂S 
• 1198104-48-1 C₁₄H₁₃BrO₂S 
• 89523-60-4 S-tert-butyl phenylmethanesulfinothioate 
• 37945-60-1 Phenyl Phenylmethanethiosulfonate 
• 4403-73-0 benzylsulfinic acid 
• 100-87-8 Benzylsulfonic acid 
• 16601-40-4 S-benzyl phenyl-methanethiosulfonate 
• 150-60-7 dibenzyl disulphide 
• 73975-55-0 benzyl 2-methoxycarbonylethyl sulphoxide 
• 64648-11-9 α-acetylthiobenzyl benzyl sulphoxide 

Relevant articles and documents

Sulfinyl chlorides through the oxidative chlorination of sulfenyl derivatives with trimethylsilyl acetate/sulfuryl chloride system

A new and useful procedure for the synthesis of sulfinyl chlorides is described involving a combined action of trimethylsilyl acetate and sulfuryl chloride as a oxidative chlorination system on sulfenyl derivatives.

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

Allicin and derivates are cysteine protease inhibitors with antiparasitic activity

Allicin and derivatives thereof inhibit the CAC1 cysteine proteases falcipain 2, rhodesain, cathepsin B and L in the low micromolar range. The structure-activity relationship revealed that only derivatives with primary carbon atom in vicinity to the thiosulfinate sulfur atom attacked by the active-site Cys residue are active against the target enzymes. Some compounds also show potent antiparasitic activity against Plasmodium falciparum and Trypanosoma brucei brucei.

Intramolecular homolytic substitution of sulfinates and sulfinamides

A general and efficient method for the synthesis of cyclic sulfi-nates and sulfinamides based on intra-molecular homolytic substitution (SHi) at the sulfur atom by aryl or alkyl radi-cals is described. Both alkyl and benzo-fused compounds can be accessed di-rectly from easily prepared acyclic pre-cursors. Enantiomerically enriched sulfur-based heterocycles were formed through an SHi process with inversion of configuration at the sulfur atom. Cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the size of the incoming radical. 2-Pyridyl and 2-qui-nolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.

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.

Atropisomer-selective ligand-coupling reactions of sulfoxides. X-Ray molecular and crystal structures for 2-(thiophen-3-yl>amino)-2-methylpropan-1-ol, 2-(2-hydroxy-1,1-dimethylethyl)-2,3-dihydronaphthoisothiazol-3-one and (R)-(+)-2-bromo-1-(tert...

1-(Alkyl- or aryl-sulfinyl)naphthalenes activated by electron-withdrawing substituents at the 2-position undergo substitution reactions on treatment with Grignard reagents.Evidence suggesting that these transformations proceed through ligand-coupling reactions of ?-sulfuranes is presented.The ligand-coupling reaction of homochiral sulfoxides with 1-naphthylmagnesium bromide furnishes atropisomeric 1,1'-binaphthyls in 60-95percent ee.Single-crystal X-ray structure determinations have been carried out on 2-(thiophen-3-yl>amino)-2-methylpropan-1-ol 18 and 2-(2-hydroxy-1,1-dimethylethyl)-2,3-dihydronaphthoisothiazol-3-one 22, compounds formed through intramolecular nucleophilic and electrophilic attack, respectively, on a neighbouring oxazoline group.The absolute configuration of (R)-(+)-1-(tert-butylsulfinyl)naphthalene 27 was determined by a single-crystal X-ray study of the 2-bromo-derivative 28.

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.

Direct Conversion of Thiols to Sulfinyl Chlorides by Sulfuryl Chloride

Sulfinyl chlorides are prepared in quantitative yield by the reaction of thiols with sulfuryl chloride/acetic acid at low temperature.

A SIMPLE AND EFFICIENT PREPARATION OF SULFINYL CHLORIDES FROM DISULFIDES AND SULFURYL CHLORIDE

Disulfides react with sulfuryl chloride in the presence of acetic acid to form the corresponding sulfinyl chlorides in nearly quantitative yield.

Reactions of Thionyl Chloride with Tetraorganotin(IV) Compounds

The reactions of thionyl chloride with tetraorganotin(IV) derivatives (R4Sn where R = CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H4CH3) bring about cleavage of tin-carbon bonds to give dialkyl/aryltin(IV) and alkyl/aryl sulphinyl chlorides.The ease of cleavage observed on the basis of the reactivities of R4Sn follows the order: n-C4H9 > n-C3H7 > C2H5 > CH3 > C6H5CH2 >> C6H4CH3.This order is not the same as commonly known in literature.