6481-72-7

Basic information

• Product Name: Benzenesulfinothioic acid, 4-chloro-, S-(4-chlorophenyl) ester
• CAS NO: 6481-72-7
• Molecular Formula: C12H8Cl2OS2
• Molecular Weight: 303.233
• Mol File: 6481-72-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzenesulfinothioic acid, 4-chloro-, S-(4-chlorophenyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfinothioic acid, 4-chloro-, S-(4-chlorophenyl) ester(6481-72-7)
• EPA Substance Registry System: Benzenesulfinothioic acid, 4-chloro-, S-(4-chlorophenyl) ester(6481-72-7)

Safety Data

• Hazardous Substances Data: 6481-72-7(Hazardous Substances Data)

Upstream product

• 933-01-7 4-chloro-benzenesulfenyl chloride 
• 108-90-7 chlorobenzene 
• 38781-27-0 Di(4-chlor-phenyl)-thio-dithiazylid 
• 13616-65-4 bis(4-chlorophenylamine) sulfide 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 

Downstream Products

• 26974-28-7 benzenethiosulfinic acid S-(4-chloro-phenyl ester) 
• 26974-31-2 1-(4-chlorophenyl)-2-chloro-1,2-dithiaethanone 
• 121955-59-7 toluene-4-thiosulfinic acid S-(4-chloro-phenyl ester) 

Relevant articles and documents

Investigations on the Lewis-acids-catalysed electrophilic aromatic substitution reactions of thionyl chloride and selenyl chloride, the substituent effects, and the reaction mechanisms

The previously established aluminium-chloride-(AlCl3)-catalysed electrophilic aromatic substitution (EAS) of benzene (PhH) with thionyl chloride (SOCl2) has been extended to toluene (PhCH3), chlorobenzene (PhCl), and phenol (PhOH). -CH3 was found to be mainly a para-director with a minor ortho-directing effect on the EAS reactions giving diaryl sulfoxides (Ar2SO). -Cl was found to be exclusively a para-director for formation of Ar2SO. All the -CH3, -Cl, and -OH groups were shown to be exclusive para-directors for formation of diaryl sulfides (Ar2S) from the EAS reactions. Although the reactions of PhH and PhCH3 with SOCl2 in the presence of AlCl 3 gave the major Ar2SO and minor Ar2S at ambient temperature, the phenol (PhOH) reaction was shown to give only the reduced sulfide (p-HOC6H4)2S with no sulfoxide (p-HOC6H4)2SO formed. The mixed diaryl sulfoxides ArSOAr′ (Ar, Ar′=C6H5, p-CH 3C6H4; C6H5, o-CH 3C6H4; and C6H5, p-ClC6H4) were produced in the AlCl3-catalysed reactions of SOCl2 with molar 1:1 PhH-PhX mixtures (X=CH3 and Cl). Efforts to enhance the yield of S-aryl arenesulfonothioates ArSO 2SAr (Ar=Ph, p-CH3C6H4, and p-ClC6H4) from the AlCl3-catalysed EAS reactions of SOCl2 were made, showing that decreasing the molar ratios of ArH/SOCl2 or lowering the temperature resulted in an increase in the product yield. A detailed mechanism has been proposed to account for the formation of ArSO2SAr. The Lewis-acid-MCl3-(M=Al and Fe)-catalysed EAS reactions of PhH with selenyl chloride (SeOCl2) were demonstrated to give the reduced diphenyl selenide (Ph2Se) and diphenyl diselenide (PhSeSePh) via novel auto-redox processes in selenium of the key EAS intermediates.