243671-61-6

Basic information

• Product Name: (Z)-2-((2-hydroxyethyl)thio)-1-p-toluenesulfonylethylene
• Synonyms: (Z)-2-((2-hydroxyethyl)thio)-1-p-toluenesulfonylethylene
• CAS NO: 243671-61-6
• Molecular Weight: 258.362
• Mol File: 243671-61-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Z)-2-((2-hydroxyethyl)thio)-1-p-toluenesulfonylethylene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-((2-hydroxyethyl)thio)-1-p-toluenesulfonylethylene(243671-61-6)
• EPA Substance Registry System: (Z)-2-((2-hydroxyethyl)thio)-1-p-toluenesulfonylethylene(243671-61-6)

Safety Data

• Hazardous Substances Data: 243671-61-6(Hazardous Substances Data)

Upstream product

• 60-24-2 2-hydroxyethanethiol 
• 13894-21-8 ethynyl p-tolyl sulfone 

Downstream Products

• 142572-72-3 (E)-2-(1-pyrrolidyl)-1-p-toluenesulfonylethylene 
• 60-24-2 2-hydroxyethanethiol 

Relevant articles and documents

Chemoselective protection of thiols versus alcohols and phenols. The Tosvinyl group

The conjugate addition of aliphatic and aromatic thiols to ethynyl p-tolyl sulphone (tosylacetylene) has been managed to afford Tosvinyl derivatives chemoselectively (in the presence of oxygen nucleophiles) and stereoselectively (isomers Z) in practically quantitative yields. The conditions of choice are: catalytic amounts of Et3N (only 0.5-1.0 mol%), a reaction temperature around 0°C and, for the less acidic thiols, CF3CH2OH or CH3CN/CF3CH2OH as the solvent. Thus, N-Boc-Cys-OMe has been quantitatively protected as its S-Tosvinyl derivative in the presence of N-Boc-Ser-OMe and N-Boc-Tyr-OMe. This novel protecting group is stable to several basic and acidic conditions; its removal is achieved at rt by treatment with an excess of pyrrolidine or at 0°C with alkanethiolate ions.