31540-75-7

Usage

Chemical structure

A benzene ring with a dichloromethyl group attached to the 1-position and a sulfonyl group attached to the same carbon, and a methyl group at the 4-position.

Type of compound

Sulfone

Functional groups

Dichloromethyl, sulfonyl, and methyl groups

Applications

Intermediate in organic synthesis for pharmaceuticals and agrochemicals; reagent in the synthesis of other organic compounds

Reactivity

Strong electrophile due to the presence of dichloromethyl and sulfonyl groups; can undergo reactions with nucleophiles

Safety precautions

Toxic and harmful if ingested or inhaled; can cause skin and eye irritation; handle with caution

Upstream product

• 67-66-3 chloroform 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 3899-90-9 3-nitrophenyl 4-methylbenzenesulfonate 
• 3937-96-0 tosylacetic acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 1666-24-6 α-benzoyl-α-(p-tolylsulfonyl)diazomethane 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 50397-64-3 methyl 2-(p-tolylsulfonyl)acetate 
• 536-57-2 p-toluene sulfinic acid 

Downstream Products

• 133228-48-5 α-chloro-5-fluoro-2,4-dinitrobenzyl p-tolyl sulfone 
• 133228-43-0 α,5-dichloro-2,4-dinitrobenzyl p-tolyl sulfone 
• 460743-34-4 α-chloro-α-(p-tolylsulfonyl)acetophenone 
• 133228-47-4 α-chloro-2,4-dinitrobenzyl p-tolyl sulfone 

Relevant academic research and scientific papers

Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides

Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.

Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms

Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to α-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like products. With X=SO2Ph, the major product was the corresponding α,α-dichloroalkyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations.

Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones

The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.

Vicarious nucleophilic substitution of hydrogen in nitrophenyl toluenesulfonates

Toluenesulfonates of nitrophenols react with carbanions possessing leaving groups giving products of the vicarious nucleophilic substitution of hydrogen. The yields and orientation depend on the reaction conditions and the structure of the reagents. The products obtained can be easily hydrolyxed to the corresponding phenols or - in certain cases - to hydroxynitrobenzaldehydes.

Sulfonyl Esters. V. A Preparation of Dichloromethyl Sulfones

α-Sulfonyl methyl esters have been chlorinated in the presence of base.Chlorination proceeds with accompanying demethoxycarbonylation to furnish dichloromethyl sulfones in good yields.