728895-67-8

Basic information

• Product Name: Benzene, 1-[(1E)-2-(3-methylphenyl)-1-nitroethenyl]-2-(methylthio)-
• CAS NO: 728895-67-8
• Molecular Formula: C16H15NO2S
• Molecular Weight: 285.367
• Mol File: 728895-67-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(1E)-2-(3-methylphenyl)-1-nitroethenyl]-2-(methylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(1E)-2-(3-methylphenyl)-1-nitroethenyl]-2-(methylthio)-(728895-67-8)
• EPA Substance Registry System: Benzene, 1-[(1E)-2-(3-methylphenyl)-1-nitroethenyl]-2-(methylthio)-(728895-67-8)

Safety Data

• Hazardous Substances Data: 728895-67-8(Hazardous Substances Data)

Upstream product

• 121905-60-0 3-methylphenylmagnesium chloride 
• 389838-02-2 (E)-1-(2-(methylthio)phenyl)-2-pyrrolidinyl-1-nitroethene 

Downstream Products

• 728895-89-4 (E)-1-[2-(methylsulfonyl)phenyl]-1-nitro-2-(m-tolyl)ethylene 

Relevant articles and documents

Easy access to 4-nitrothiochroman S,S-dioxides via ring-enlargement from 3-nitrobenzo[b]thiophene

The (E)-2-aryl-1-[2-(methylthio)phenyl]-1-nitroethylenes 5 can easily be oxidized to the relevant sulfones 6 and effectively subjected to cyclization via an intramolecular Michael addition after metallation with lithium bis(trimethylsilyl)amide in THF. After quenching with ammonium chloride the 3-aryl-4-nitrothiochroman S,S-dioxides 2 are obtained as diastereomeric mixtures in good to excellent yields. Both yields and stereochemistry of the ring-closure step appear to be influenced by steric effects of the 3-aryl moiety. As sulfides 5 derive from an initial ring opening of 3-nitrobenzo[b]thiophene (1), the overall 1 to 2 process can be considered as an effective 5 to 6 ring enlargement of the sulfur heterocycle. A conformational 1H NMR and molecular-mechanics investigation on the isolated diastereomeric 2 has also been accomplished.