75421-91-9

Basic information

• Product Name: 1H-Pyrrole, 1-methyl-3-[(4-methylphenyl)sulfinyl]-
• CAS NO: 75421-91-9
• Molecular Formula: C12H13NOS
• Molecular Weight: 219.307
• Mol File: 75421-91-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 1-methyl-3-[(4-methylphenyl)sulfinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 1-methyl-3-[(4-methylphenyl)sulfinyl]-(75421-91-9)
• EPA Substance Registry System: 1H-Pyrrole, 1-methyl-3-[(4-methylphenyl)sulfinyl]-(75421-91-9)

Safety Data

• Hazardous Substances Data: 75421-91-9(Hazardous Substances Data)

Upstream product

• 96-54-8 N-Methylpyrrole 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 6873-87-6 N-butyl-4-methylbenzene-1-sulfinamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 536-57-2 p-toluene sulfinic acid 

Downstream Products

• 1381847-86-4 C₁₂H₁₃NS 
• 113976-53-7 2-Chloro-1-methyl-3-(toluene-4-sulfonyl)-1H-pyrrole 
• 113976-56-0 2,5-Dichloro-1-methyl-3-(toluene-4-sulfonyl)-1H-pyrrole 
• 113976-58-2 2-Chloro-1-methyl-3-(toluene-4-sulfinyl)-1H-pyrrole 

Relevant articles and documents

Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water

Abstract: The first example of the sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to a wide range of functionalized diaryl sulfoxides.

Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides

An unexpected time-controlled highly selective C3-or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.

Synthesis and Rearrangement of 2-(Arylsulfinyl)- and 2-(Alkylsulfinyl)pyrroles

Pyrrole and N-methylpyrrole reacted with aryl- and alkylsulfinyl chlorides, at 0 deg C, to give the corresponding 2-sulfinylpyrroles as the major products only when contact of the products with the liberated hydrogen chloride was minimized or eliminated.If this precaution was not taken, the 3-sulfinylpyrroles were the principle products.In contrast, N-(phenylsulfinyl)succinimide (2a) reacted, at room temperature, with a variety of pyrroles to produce the 2-phenylsulfinyl compounds in good yields.The 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrroles undergo a remarkably facile acid-promoted rearrangement to the isomeric 3-sulfinylpyrroles.This transposition is, at least in part, an intermolecular process as demonstrated by crossover experiments.