4-Nitrobenzenesulfonyl chloride is used as an intermediate for the synthesis of pharmaceuticals like foscmprenavir, darunavir and amprenavir. It is involved in the preparation of N-nosyl-alpha-amino acid for peptide synthesis. It is also used for stereoselective α-glucosylation of partially protected carbohydrates in association with silver tri-fluoromethanesulfonate, N,N-dimethylacetamide and triethylamine. It is widely used for the synthesis of hydroxylamines of sulfadiazine, sulfamethoxazole and [Cu(bipy)2Cl](nbs) (1) (bipy = 2,2'-bipyridine, nbs = 4-nitrobenzenesulfonate).
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
4-Nitrobenzenesulfonyl chloride is used as an intermediate for the synthesis of pharmaceuticals like foscmprenavir, darunavir and amprenavir. It is involved in the preparation of N-nosyl-alpha-amino acid for peptide synthesis. It is also used for stereoselective α-glucosylation of partially protected carbohydrates in association with silver tri-fluoromethanesulfonate, N,N-dimethylacetamide and triethylamine. It is widely used for the synthesis of hydroxylamines of sulfadiazine, sulfamethoxazole and [Cu(bipy)2Cl](nbs) (1) (bipy = 2,2′-bipyridine, nbs = 4-nitrobenzenesulfonate).
Solubility
Soluble in toluene, tetrahydrofuran, methylene chloride and ethyl acetate. Insoluble in water.
Notes
Moisture sensitive. Incompatible with strong oxidizing agents and strong bases.
RUO – Research Use Only
General References:
- Reagent for formation of 4-nitrobenzenesulfonyl ('Nosyl', Ns) derivatives of alcohols and amines. Nosylamides, formed from amines in the presence of, e.g. triethylamine, are stable to strong acids and bases, but are selectively cleaved by thiolates, e.g. PhSH or mercaptoacetate: Tetrahedron Lett., 36, 6373 (1995). See also 2-isomer (preceding entry).
- Marchenko, M.; Thomson, A.; Ellis, T. N.; Knuckley, B.; Causey, C. P. Development of a clickable activity-based protein profiling (ABPP) probe for agmatine deiminases. Bioorg. Med. Chem. 2015, 23 (9), 2159-2167.
- Hfaiedh, A.; Yuan, K.; Ammar, H. B.; Hassine, B. B.; Soule, J. F.; Doucet, H. Eco-Friendly Solvents for Palladium-Catalyzed Desulfitative C[BOND]H Bond Arylation of Heteroarenes. ChemSusChem 2015, 8 (10), 1794-1804.