353243-90-0

Basic information

• Product Name: 3-methoxybenzenesulfinyl chloride
• Synonyms: 3-methoxybenzenesulfinyl chloride
• CAS NO: 353243-90-0
• Molecular Weight: 190.65
• Mol File: 353243-90-0.mol

Chemical Properties

• CAS DataBase Reference: 3-methoxybenzenesulfinyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxybenzenesulfinyl chloride(353243-90-0)
• EPA Substance Registry System: 3-methoxybenzenesulfinyl chloride(353243-90-0)

Safety Data

• Hazardous Substances Data: 353243-90-0(Hazardous Substances Data)

Upstream product

• 15570-12-4 3-methoxybenzenethiol 
• 353243-87-5 (2-((3-methoxyphenyl)sulfinyl)ethyl) trimethylsilane 
• 353243-82-0 3-methoxyphenyl 2-(trimethylsilyl)ethyl sulfide 

Downstream Products

• 134478-45-8 2-(3-methoxyphenylthio)thiophene-3-carboxylic acid 
• 134478-48-1 2-(3-methoxyphenylthio)thiophene-3-carboxylic acid S-oxide 
• 134478-60-7 2-(3-Methoxy-phenylsulfanyl)-thiophene-3-carbonyl chloride 
• 134478-98-1 2-(3-Methoxy-phenylsulfanyl)-thiophene-3-carboxylic acid dimethylamide 
• 134478-46-9 N,N-dimethyl-2-(3-methoxyphenylthio)-3-thenylamine 

Relevant articles and documents

Oxidative fragmentations of 2-(trimethylsilyl)ethyl sulfoxides - Routes to alkane-, arene-, and highly substituted 1-alkenesulfinyl chlorides

The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is suitable for most alkane- and arenesulfinyl chlorides (3), but is limited to highly substituted vinylic sulfinyl chlorides. 1-Alkenyl 2-(trimethylsilyl)ethyl sulfoxides with reduced double bond substitution (6, 7, 11) succumb to reactions involving chlorination of the double bond. The β-effect of silicon is invoked to explain the ability of the 2-(trimethylsilyl)ethyl group to induce C-S bond scission under the oxidative cleavage reaction conditions. A mechanism is offered to account for the role played by the β-silicon atom of the 2-(trimethylsilyl)ethyl group. Indeed, the silicon atom is self-sacrificial in that it diverts the course of the reaction from the usual α-carbon chlorination mode to one of oxidative cleavage, whereby the 2-(trimethylsilyl)ethyl group is lost. The overall reaction calls upon the ability of silicon atoms to donate electron density by hyperconjugation.

POTENTIAL ANTIDEPRESSANTS AND INHIBITORS OF 5-HYDROXYTRYPTAMINE AND NORADRENALINE RE-UPTAKE IN THE BRAIN: N,N-DIMETHYL-(ARYLTHIO)THENYLAMINES AND N,N-DIMETHYL-2-(THIENYLTHIO)BENZYLAMINES

3-(3-Methoxyphenylthio)thiophene-2-carboxylic acid (IV) and 2-(3-methoxyphenylthio)thiophene-3-carboxylic acid (VII) were transformed via acid chlorides and dimethylamides to the amines V and VIII which were demethylated to the phenolic amines VI and IX.N