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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).
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant