6640-56-8

Usage

Structure

A benzene ring with a methyl group (CH3) and a sulfanyl group (S) attached to it, and a nitrophenyl group (-C6H4NO2) attached to the sulfur.

Physical properties

Yellow solid.

Molecular weight

237.30 g/mol.

Uses

Organic synthesis, pharmaceutical research (anti-cancer and anti-inflammatory drugs), precursor in the production of various compounds, and as a reagent in chemical reactions.

Safety precautions

Potential health hazards, including irritant and toxic effects; should be handled and stored carefully.

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 137-06-4 2-thiocresol 
• 100-00-5 4-chlorobenzonitrile 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 108-88-3 toluene 
• 40208-36-4 N-(p-nitrophenylthio)morpholine 

Downstream Products

• 126348-48-9 4-(toluene-2-sulfonyl)-aniline 
• 76590-35-7 4-((2-methylphenyl)thio)aniline 
• 42085-91-6 (4-nitro-phenyl)-o-tolyl sulfone 

Relevant academic research and scientific papers

Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors

In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.

Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides

NiCl2·6H2O efficiently catalyzes the C-S bond formation by the cross-coupling of aryl iodides with thiols in tetrabutylammonium bromide (TBAB) in excellent yield. The reaction functions in air and the NiLn-TBAB can be recovered and recycled without the loss of activity.

Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides

S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).

Arene sulfenylation by arenesulfenamides and arenesulfenylacetates

Two systems for arene sulfenylation were investigated: arenesulfenamides in the presence of SO3 and sulfenylacetate complexes with AlBr3.A preference for the second reagent was demonstrated for sulfenylation of substrates bearing donor substituents. - Key words: arenesulfenamides; arenesulfenylacetates; diarenesulfides.