91110-67-7

Usage

Physical State

colorless liquid

Odor

pungent

Reactivity

highly reactive

Uses

+ As a reagent in organic synthesis for the introduction of the sulfonylmethyl group
+ In the pharmaceutical industry for the synthesis of various pharmaceuticals
+ As a building block in the production of agrochemicals and other specialty chemicals
+ Potential use in the treatment of various diseases and disorders

Hazards

Handle with caution as it can be hazardous if mishandled.

Upstream product

• 107623-15-4 (2-chlorobenzyl)(phenyl)sulfane 
• 873-55-2 sodium benzenesulfonate 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 10175-31-2 1-(2-chlorophenyl)-N,N-dimethylmethanamine 
• 98-80-6 phenylboronic acid 

Downstream Products

• 25144-38-1 (E)-2,2'-dichlorostilbene 
• 20657-43-6 (Z)-1,2-bis(2-chlorophenyl)ethene 
• 109810-04-0 4-benzenesulfonyl-4-(2-chloro-phenyl)-heptanedinitrile 
• 101118-90-5 4-benzenesulfonyl-4-(2-chloro-phenyl)-butyronitrile 

Relevant academic research and scientific papers

One-pot synthesis of sulfones via Ni(II)-catalyzed sulfonylation of boronic acids, Na2S2O5 and benzylic ammonium salts

A one-pot nickel-catalyzed synthesis of (hetero)aryl alkyl sulfones from readily available boronic acids, sodium metabisulfite and benzylic ammonium salts as electrophiles is described. This general and efficient synthetic process is of broad scope, occurs in two steps, and delivers structural diverse sulfones, and the intermediate sulfinate is isolated. The transformation exhibits application of benzylic ammonium salts as novel electrophiles for direct insertion of SO2 as a novel area to be investigated.

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates

A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).