342631-38-3

Basic information

• Product Name: (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one
• Synonyms: (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one
• CAS NO: 342631-38-3
• Molecular Weight: 302.781
• Mol File: 342631-38-3.mol

Chemical Properties

• CAS DataBase Reference: (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one(342631-38-3)
• EPA Substance Registry System: (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one(342631-38-3)

Safety Data

• Hazardous Substances Data: 342631-38-3(Hazardous Substances Data)

Upstream product

• 4892-02-8 Methyl thiosalicylate 
• 342631-26-9 1-(3-Chlorophenyl)-3-[2-(methoxycarbonyl)phenylthio]propyne 
• 342631-19-0 3-[2-(Methoxycarbonyl)phenylthio]propyne 
• 625-99-0 3-iodochlorobenzene 

Downstream Products

• 2527-63-1 2,2'-dithiobis(N-phenylbenzamide) 
• 770-23-0 (E)-3-(3-chlorophenyl)propenal 
• 5459-63-2 bis[2-(methoxycarbonyl)phenyl]disulfide 

Relevant articles and documents

A general and highly regio and stereoselective method for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis

A palladium-copper-catalysed procedure for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h is developed. 3-[2-(Methoxycarbonyl)phenylthio]propyne 2 reacts with aryl iodides 3a-3h in the presence of bis(triphenylphosphine)palladium(II) dichloride, copper(I) iodide and triethylamine in acetonitrile to furnish the disubstituted alkynes 4a-4h in good yields (70-84%). These on alkaline hydrolysis and subsequent cyclisation of the carboxylic acids formed with copper(I) iodide (20 mol%) and triethylamine in tetrahydrofuran under reflux afford (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h in 61-70% yield rather than the expected benzoxathiepinones 6. The reactions of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a and 5g with nucleophites and the hydrogenation of compounds 5a, 5b and 5d are also studied.

Novel heteroannulation through copper catalysis: A highly regio- and stereoselective synthesis of 2-substituted 3,1-benzoxathiinones

A highly regio- and stereoselective method, comprising a cuprous iodide-catalysed cyclisation as a key step, gives an easy access to (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 16-22.