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98-74-8 - 4-Nitrobenzenesulfonyl chloride, 97% - A18512 - Alfa Aesar

A18512 4-Nitrobenzenesulfonyl chloride, 97%

CAS Number
98-74-8
Synonyms

Size Price ($) Quantity Availability
25g 49.68
100g 129.60
500g 515.87
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4-Nitrobenzenesulfonyl chloride, 97%

MDL
MFCD00007445
EINECS
202-697-9

Chemical Properties

Formula
C6H4ClNO4S
Formula Weight
221.62
Melting point
76-80°
Boiling Point
143-144°/1.5mm
Sensitivity
Moisture Sensitive
Solubility
Soluble in toluene, tetrahydrofuran, methylene chloride and ethyl acetate. Insoluble in water.

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).

Notes

Moisture sensitive. Incompatible with strong oxidizing agents and strong bases.

Literature 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).

/n

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H402-H412

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful to aquatic life. Harmful to aquatic life with long lasting effects.

Precautionary Statements: P260-P273-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
746543
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.90
TSCA
Yes

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