1309446-60-3

Basic information

• Product Name: ethyl 4-(3-((4-chlorophenyl)thio)-5-(trimethylsilyl)thiophen-2-yl)benzoate
• Synonyms: ethyl 4-(3-((4-chlorophenyl)thio)-5-(trimethylsilyl)thiophen-2-yl)benzoate
• CAS NO: 1309446-60-3
• Molecular Weight: 447.094
• Mol File: 1309446-60-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 4-(3-((4-chlorophenyl)thio)-5-(trimethylsilyl)thiophen-2-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-(3-((4-chlorophenyl)thio)-5-(trimethylsilyl)thiophen-2-yl)benzoate(1309446-60-3)
• EPA Substance Registry System: ethyl 4-(3-((4-chlorophenyl)thio)-5-(trimethylsilyl)thiophen-2-yl)benzoate(1309446-60-3)

Safety Data

• Hazardous Substances Data: 1309446-60-3(Hazardous Substances Data)

Upstream product

• 1213-40-7 S-(4-chlorophenyl)benzene thiosulfonate 
• 1176869-72-9 {5-[(4-methoxyphenyl)sulfinyl]-2-thiophenyl}(trimethyl)silane 
• 1176869-76-3 (4-((4-chlorophenyl)thio)-5-((4-methoxyphenyl)sulfinyl)thiophen-2-yl)trimethylsilane 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 18245-28-8 2-(trimethylsilyl)thiophene 

Relevant articles and documents

Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide-magnesium exchange

The aryl sulfoxide moiety allows an expedient two-step difunctionalisation of readily available diaryl sulfoxides. Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes (furans, thiophenes, benzofurans and pyridines) were prepared in a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metallation-directing group, allowing smooth ortho-magnesiation with TMPMgCl.LiCl (TMP=tetramethylpiperidine). After a quenching reaction with an electrophile, the resulting sulfoxide is converted into a second magnesium reagent with iPrMgCl.LiCl (sulfoxide-magnesium exchange), which can be trapped with various electrophiles. Highly chemoselective TMPMgCl.LiCl and iPrMgCl.LiCl are compatible with a broad range of functional groups (e.g., F, Cl, CF 3, CN, CO2tBu, alkynyl, ethers, thioethers). Large-scale reactions (25-40 mmol) and the preparation of fully functionalised furans and thiophenes are also reported. Successful exchange: Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes were prepared in a two-step sequence, triggered by an aryl sulfoxide group. The chemoselective reagents used, TMPMgCl.LiCl (TMP=tetramethylpiperidine) and iPrMgCl.LiCl, are compatible with a broad range of functional groups (see scheme; E=electrophile.)