2-Nitrobenzenesulfenyl chloride is used as a reagent for N-protection as N-2-nitrophenylsulfenyl (Nps) derivatives, in amino acids and peptides and nucleosides.
Norman Kharasch; Herbert L. Wehrmeister; Henry Tigerman. Derivatives of Sulfenic Acids. I. Reactions of 2-Nitrobenzenesulfenyl Chloride, 2,4-Dinitrobenzenesulfenyl Chloride and of the Corresponding Sulfenyl Thiocyanates with Olefins and with Methyl Ketones. J. Am. Chem. Soc. 1947, 69, (7), 1612-1615.
Reagent for N-protection as N-2-nitrophenylsulfenyl (Nps) derivatives, in amino acids and peptides: J. Am. Chem. Soc., 85, 3660 (1963); 87, 99 (1965); Biochemistry, 7, 971, 980 (1968); Synthesis, 512 (1985); Helv. Chim. Acta, 66, 602 (1983), and nucleosides: J. Org. Chem., 54, 2321 (1989). The Nps group is readily cleaved by dilute acid. For cleavage with thioacetamide, see: Helv. Chim. Acta, 49, 1330 (1966).
The chemistry of sulfenyl halides has been reviewed: Synthesis, 563, 617 (1971).
Gefahrenhinweise (EU): H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Obtain special instructions before use. Wear eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.