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Benzenesulfonyl chloride reacts with Grignard reagents to form oxindoles from N-unsubstituted indoles. It is widely used to check the assay of thiamine in different food products. It is involved in the synthesis of alpha-disulfones, sulfonamides and sulfoante esters as precursor. It is a derivatization reagent for the determination of various amines in waste water and surface water at the sub-ppb level by gas chromatography-mass spectrometry. It is common reagent used in Hinsberg test for detection and distinguishing the type of amines as primary, secondary and tertiary amines.
Reacts with ß-hydroxy esters in pyridine to give ß-lactones which, at higher temperatures eliminate CO2 in a stereospecific alkene synthesis: J. Am. Chem. Soc., 94, 2000 (1972); J. Org. Chem., 39, 1322, 1650 (1974):
Alternatively, MgBr2 induces a ring-opening reaction leading to ß-unsaturated acids. See, e.g.: Synth. Commun., 19, 2243 (1989).
Yuan, K.; Sang, R.; Soule, J. F.; Doucet, H. Desulfitative Pd-catalysed coupling reaction using benzenesulfonyl chlorides and enones as the coupling partners. Catal. Sci. Technol. 2015, 5 (5), 2904-2912.
Delgertsetseg, B.; Javkhlantugs, N.; Enkhtur, E.; Yokokura, Y.; Ooba, T.; Ueda, K.; Ganzorig, C.; Sakomura, M. Detailed investigation of dependencies of photovoltaic performances of P3HT:PC61BM based solar cells on anodic work function modified by surface treatment of indium-tin-oxide electrode with benzenesulfonyl chloride derivatives. Org. Electron. 2015, 23, 164-170.
Gefahrenhinweise (EU): H302-H314-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.