4- benzenesulfonyl chloride

Insoluble in cold water soluble in ether and alcohol.1 Reacts slowly with water to form benzenesulfonic acid and hydrogen chloride.2 

Severely irritates the eyes and causes skin burns. Causes severe internal irritation if taken by mouth.2 

Package Lots. Place the compound in a separate container labeled for disposal by burning. Burn in an incinerator equipped with afterburner and scrubber.7 

Small Quantities. Wear nitrile rubber gloves, laboratory coat, and eye protection. Work in the fume hood. Sodium hydroxide solution (60 mL of 2.5 M) is added to a 100-mL, three-necked, round-bottom flask equipped with a stirrer, dropping funnel, and thermometer. Benzenesulfonyl chloride (0.05 mol, 8.9 g, or 6.5 mL) is added dropwise. If the reaction is sluggish (no dissolution or rise in temperature) at first, heat the mixture on a steam bath to about 90°C. When the initially added benzenesulfonyl chloride has dissolved, add the remainder dropwise. After addition is complete, continue heating until a clear solution is obtained. Cool the mixture is cooled to room temperature, neutralize with 10% hydrochloric acid, and wash into the drain.5 

Reactions for Spillage and Waste Disposal QHjSOp + 2NaOH- H=° C fjSO Na + NaCJ + H.O 

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The carbonylation of aryl halides under mild conditions in the presence of CsF afford.s the acid fluoride 490 in good yields. Unlike acyl chlorides, acyl fluorides are inert toward Pd(0) catalyst[345]. Benzenesulfonyl chloride (491) undergoes desulfonylation-carbonylation to give the benzoate 492 in the presence of titanium tetralkoxide at 160 °C[346]. 

The O-alkyl derivatives of those A-oxides, which exist partly or entirely as (V-hydroxy tautomers, may be made by primary synthesis (as above) or by alkylation. Thus, 5,5-diethyl-1-hydroxybarbituric acid (936 R = H) with methyl iodide/sodium ethoxide gives the 1-methoxy derivative (936 R = Me) or with benzenesulfonyl chloride/ethoxide it gives the alkylated derivative (936 R = PhS02) (78AJC2517). 

Benzenesulfonyl chloride [98-09-9J M 176.6, m 14.5°, b 120°/10mm, 251.2°/760mm(dec), d 1.384. Distd, then treated with 3mole % each of toluene and AICI3, and allowed to stand overnight. The free benzenesulfonyl chloride was distd off at 1mm pressure, and then carefully fractionally distd at 10mm in an all-glass column. [Jensen and Brown J Am Chem Soc 80 4042 795[Pg.121]

A thiazole derivative that incorporates a fragment of the amphetamine molecule shows some CNS stimulant activity more specifically, the compound antagonizes the depression caused by overdoses of barbiturates and narcotics. Reaction of benzalde-hyde with sodium cyanide and benzenesulfonyl chloride gives the toluenesulfony1 ester of the cyanohydrin (141). Reaction of this with thiourea leads directly to aminophenazole (143) It is probable the reaction proceeds by displacement of the tosylate by the thiourea sulfur to give 142 addition of the amino group to the nitrile followed by tautomerization affords the observed product. ... 

Phenylphenylsulfanyl)benzenesulfonyl Chloride (Fragment Arene —S —Arene—Arene)... 

The decomposition of 2-(2-phenylphenylsulfanyl)benzenesulfonyl chloride (5) at elevated temperatures leads to the formation of tribenzo[6,c/,/]thiepin(6) in 24% yield by an intramolecular cyclization pathway. Mechanistically, this thermolysis is comparable to the Pschorr reaction (cf. Houben-Weyl, Vol. 5/2b, p 420 Vol. 10/3, p 189) however, copper(I) chloride is now preferred as a catalyst, without any solvent.4 In the thermolysis of 5, 4-phenyldibenzothiophene (7) is formed as a byproduct in 14% yield. Octachloronaphthalene can also be employed as a catalyst however, the yield of 6 is somewhat lower (19%).4... 

Phenylphenylsulfanyl)benzenesulfonyl chloride (10 g, 28 mmol) and CuCI (27 mg, 0.28 mmol) were mixed together in a glass vessel under an N2 atmosphere. The contents were stirred and the vessel was... 

Benzenesulfonic acid, 4-methyl-, monohydrate [6192-52-5], 44 Benzenesulfonyl chloride, 4-methyl- [98-59-9], 97... 

Pure samples are best prepd by the methylation of acetanilide or benzanilide to the N-methyl compds followed by acid hyd. It has been prepd commercially by the action of methyl ale on aniline in an autoclave under press and by the action of methyl amine on halobenzenes. For a summary of prepns see Refs 6 9. It may be separated from aniline and dime thy laniline by treatment of the mixt with benzenesulfonyl chloride. Dimethylamline fails to react and is extd out with dil acid. Aniline forms benzenesulfonanilide which is acidic and is removed by washing with dil base, leaving the N-methylbenzenesulfonanilide. Purified N-methylaniline is obtd by acid hyd (Ref 8). N-Methylaniline is used as an additive to raise the octane no of motor fuels (Ref 6), as a dyestuff intermediate (Ref 3), in the prepn of Tetryl (see below), and in the prepn of Methylcentralite (Encycl, Vol 2, C137-R)... 

Ilydriodic acid in reduction of m-nitro-benzenesulfonyl chloride to m-nitrophenyl disulfide, 40, 80 Hydrogenation, of diethylisonitroso-malonate to diethyl aminomalo-nate over palladium-on-charcoal, 40, 24... 

Benzenesulfonyl chloride, 4-methyl- [p-Tol-uenesulfonyl chloride], 55, 57, 59 Benzenethiol [Phenol, thio-], 55, 122 Benzenethiol, copper(I) salt [Thiophenol, copper(I) salt], 55, 123 Benzenethiol, lithium salt [Thiophenol, lithium salt], 55, 1 22 Benzoic acid, 2-amino- [Anthramlic acid], p bromination of, 55, 23... 

Polysulfonation of self-polycondensation of 4-(phenylthio)benzenesulfonyl chloride was also used to prepare poly(arylene sulfide sulfone)s.245,246 Condensation of diphenyl sulfide with d -oxydibenzenesulfonic acid or d.d -thiodibcn/cnc-sulfonic acid247 or by poly etherification of poly condensation of DC DPS with d.d -dihydroxydiphenol sulfide occurred.5... 

Analogously, sulfonyl halides such as benzenesulfonyl chloride 1764 are reduced by excess TIS 17 to disulfides such as diphenyl sulfide 1765 [22, 23] (Scheme 12.5). 

The classic syntheses of the antibacterial sulfonamides involve reaction of the appropriate arylamine with an acid addition salt of p-amino-benzenesulfonyl chloride, or p-nitrobenzenesulfonyl chloride followed by reduction. Chemical interest largely resides in preparation of the corresponding arylamines. For the synthesis of sulfacytine (134), N-ethyl uracil (131) was converted to its thioamide (132) by reaction with phosphorous pentasulfide. The newly introduced sulfur is then displaced with ammonia in methanol to give 133. Standard reactions complete... 

In recent years, a variety of aryl boronic acids are commercially available, albeit in some cases they may be expensive for large scale purposes. During our work in the mid-1990 s boronic acid (II) was not commercially available and so two different protocols were used to prepare this acid. The first approach involved the transmetallation with n-butyl lithium of aryl bromide (I) and trapping the lithio species generated with trialkyl borate followed by an acid quench. Aryl bromide (I) is easily prepared by reaction of o-bromobenzenesulfonyl chloride with 2-propanol in the presence of pyridine as a base. The second approach was a directed metallation of isopropyl ester of benzene sulfonic acid (VII), to generate the same lithio species and reaction with trialkyl borate. The sulfonyl ester is prepared by reaction of 2-propanol with benzenesulfonyl chloride. From a long-term strategy the latter approach is... 

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