Benzenesulfonyl fluoride

Bacterial Extract Protease CocktaiL Inhibitors present are pepstatin A, 4-(2-amino-ethyl)benzenesulfonyl fluoride (AEBSF), rrans-epoxysuccinyl-L-leucylam-ido(4-guanidino)butane (E-64), bestatin, and sodium EDTA. 

Herlem et al463 have observed that asphaltene is dissolved in fluorosulfuric acid and the process is accompanied by strong redox reactions (SO2 and HF evolution). The products are mainly functionalized by SO3H groups, but SO2F groups were also detected by XPS. Indeed, model studies with benzene showed the formation of benzenesulfonic acid, diphenylsulfone, and benzenesulfonyl fluoride. For alkylbenzenes, sulfonation was not accompanied by cracking of the alkyl chain. 

Benzeneselenenyl halides, 34-37 Benzeneselenenyl iodide, 36 Benzeneseleninic anhydride, 37—39 Benzenesulfenyl chloride, 39-40 Benzenesulfonyl fluoride, 40 Benzenesulfonylnitrile oxide, 40-41 1 -Benzenesulfonyl-2-trimethylsilylethane, 41-42... 

Representatives of this class of inhibitors are DFP (diisopropylfluoro-phosphate), PMSF (phenylmethylsulfonyl fluoride), APMSF (4-aminophe-nyl)-methanesulfonyl, AEBSF (4-(2-aminoethyl)-benzenesulfonyl fluoride), FK-448 (4-(4-isopropylpiperadinocarbonyl) phenyl 1,2,3,4,-tetrahydro-1-naphthoate methanesulfonate), camostat mesilate (7V,/V -dimethyl carba-moylmethyl-/)-(/> -guanidino-benzoyloxy)phenylacetate methanesulfonate), and Na-glycocholate. The organophosphorus inhibitors DFP and PMSF are potent irreversible inhibitors of serine proteases. Due to their... 

Higher temperatures (100-125°) are employed when carboxyl or nitro groups.are on the nucleus. Benzenesulfonyl fluoride is obtained in 62% yield by the action of excess fluorosulfonic acid at 20° on benzene in an iron vessel. ... 

A solution of CF3TMS (2.84 g. 20 mmol) in THF (10 mL) was added portionwise to a stirred suspension of benzenesulfonyl fluoride (10 mmol) and TASF(Me) (1 mmol) in petroleum ether (bp 60-80"C) (10 mL) at 25 C over 10-15 min under argon. The mixture was stirred for 0.5 h, then treated with H20 (30mL), and extracted with petroleum ether (30 mL). The organic phase was washed with H20 (4x 50 mL), dried (MgS04) and concentrated. The product was distilled yield 99% bp 118-119 C/20Torr n ° 1.4637. 

Sanecki P, Kaczmarski K (1999) The voltammetric reduction of some benzenesulfonyl fluorides, simulation of the ECE mechanism and determination of the potential variation of the transfer coefficient by using the compounds with two reducible groups. J Electroanal Chem 471 14-25... 

Benzenesulfonyl Fluoride. For experiments with fluorosulfonic acid, Steinkopf recommends the use of an iron vessel with a screw top fitted with a mercury-seal stirrer, dropping funnel, thermometer well, and gas-exit tube. A small open-top iron or platinum container without a stirrer can be used only in very small-scale fluorosulfonations. 

To 225 g. (2.25 moles) of -fluorosulfonic acid in an iron container is added 55 g. (0.7 mole) of benzene with stirring during six hours at 16-20°. After an additional nine hours at the same temperature, with continued stirring, the reaction mixture is poured on ice and extracted with ether the ether layer is washed with water to which sufficient calcium carbonate is added to neutralize the acid, the ether solution is separated and concentrated, and the residue is distilled with steam. There is obtained 77.5 g. (62% yield) of an oil that distils at 90-91°/14 mm. and 203-204°/ 760 mm. 4°° 1.3286 and nif 1.4932. The residue from the steam distillation contains 9.5 g. of phenyl sulfone. Benzenesulfonyl fluoride may be obtained also by allowing benzenesulfonyl chloride to stand with four times its weight of fluorosulfonic acid at room temperature for twenty-four hours. 

A mixture of 1,3-dicyano-l-trimethylsiloxycyclobutane, benzenesulfonyl fluoride, and tetraethylammonium fluoride stirred 6 days under Ng 1,3-dicyano-l-ben-zenesulfonyloxycyclobutane. Y 61%. - Siloxy derivs. of relatively acidic alcohols can be efficiently converted to sulfonates by the above method. F. e. s. P. Ykman and H. K. Hall, Jr., J. Organometal. Chem. 116, 153 (1976). 

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