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4-Bromobenzenesulfonyl chloride is used as activating agent in the synthesis of oligodeoxyribo- and oligoribo- nucleotides in solution. It also used in the synthesis of 4-(N-allylsulfamoyl)phenylboronic acid and in protection of amines as 4-bromobenzenesulfonamides.
Reese CB.; Pei-Zhuo Z. J. Phosphotriester approach to the synthesis of oligonucleotides: a reappraisal.. Chem. Soc. Perkin Trans. I. 1993, 1 (9), 2291-2301.
Xiaobao Li.; Justin Pennington.; John F Stobaugh.; Christian Schöneich. Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH. Analytical Biochemistry. 2008, 372 (2), 227-236.
Used in protection of amines as 4-bromobenzenesulfonamides: Synth. Commun., 18, 1615 (1988); Tetrahedron Lett., 30, 2399 (1989).
Alcohols are converted to 4-brombenzenesulfonate ("brosylate") esters with enhanced leaving group ability relative to the commoner tosylate; see, e.g.: Carbohydr. Res., 46, 53 (1976).
In the presence of potassium carbonate and a phase-transfer catalyst, N,N'-disubstituted ureas are dehydrated to carbodiimides in high yield: Synthesis, 520 (1987).
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious 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