Benzenediazonium-4-sulfonate

Benzenediazonium-2-carboxylate, 2655 Benzenediazonium-3-carboxylate, 2656 Benzenediazonium-4-carboxylate, 2657 Benzenediazonium chloride, 2223 Benzenediazonium hydrogen sulfate, 2311 Benzenediazonium iodide, 2243 Benzenediazonium nitrate, 2268 Benzenediazonium-4-oxide, 2182 Benzenediazonium perchlorate, 2225 Benzenediazonium-2-sulfonate, 2185 Benzenediazonium-4-sulfonate, 2186 Benzenediazonium tetrachlorozincate, 3469 Benzenediazonium tetrafluoroborate, 2216 Benzenediazonium tetraphenylborate, 3870a Benzenediazonium tribromide, 2220 Benzenediazonium triiodide, 2247... 

Several of these internal diazonium salts, prepared by diazotisation of anthranilic acids, are explosive in the solid state, or react violently with various materials. Individually indexed compounds (including analogous sulfonates) are Benzenediazonium-2-carboxylate, 2655 Benzenediazonium-2-sulfonate, 2185 Benzenediazonium-3 or 4-carboxylate, 2656... 

A) Diazotizalion of Sulfanilic Acid.—A mixture of 105 g. (0.5 mole) of sulfanilic acid dihydrate, 26.5 g. (0.25 mole) of anhydrous sodium carbonate, and 500 cc. of water is heated and stirred until all the sulfanilic acid has dissolved, and the solution is then cooled in an ice bath to 15° (sodium sulfanilate begins to crystallize at this temperature). A solution of 37 g. (0.54 mole) of sodium nitrite in 100 cc. of water is added and the resulting solution is poured at once onto a mixture of 106 cc. (1.25 moles) (Note i) of concentrated hydrochloric acid (sp. gr. 1.18) and 600 g. of ice contained in a 2-I. beaker. The solution, from which -benzenediazonium sulfonate separates on stirring, is allowed to stand in an ice bath for fifteen to twenty-five minutes, during which time the naphtholate solution is prepared. 

Di azobenzene Sulfonic Acid. See Benzenediazonium Sulfonic Acid in Vol 2 , p B57-L... 

Benzene diazo- and diazonium derivs (cont d) benzenediazonium sulfocyanate 2 BS7 benzenediazonium sulfonic acid and derivs 2 B57... 

Diazobenzene sulfonic acid see Benzenediazonium sulfonic acid 2 B57... 

Benzenediazomum-2-carboxylate, 46,1194 Benzenediazonium chloride, 394, 838 Benzenediazonium fluoroborate, 394 Benzenediazonium nitrate, 328 Benzenediazonium sulfonate, 713 Benzene-maleic anhydride 1 2 adduct, 557 Benzenesulfinyl fluoride, 849 Benzenesulfonamides, 46-47, 48... 

As a test of this mechanism, the coupling of p-benzenediazonium sulfonate 21 with phenol was examined. In solution it couples in the para position, but a-cyclodextrin... 

The ratio between the isomers obtained in coupling with 1,3- and 1,5-naphtholsulfonic acids depends on the reactivity of the diazo component. Energetic ones, such as the 2,4-dinitrobenzenediazonium compound, essentially couple only with l-naphthol-3-sulfonic acid [3771-14-0] in the para position, but 4-chloro-benzenediazonium salt (a weaker diazo) attacks the ortho position. Both isomers result when mononitrobenzenediazonium compounds are used. The tendency to couple para is greater in l-naphthol-5-sulfonic acid [117-59-9] C QHgO S (21). For the combination of... 

The cyclophane 12.30 reacts with 4.8 equivalents of benzenediazonium-4-sulfonate to give the tetraarylazo derivative 12.31 in good yield. In contrast to the starting material the product is water-soluble. Without going into details, the authors mention a spectrophotometrically determined pifa-value of 10 which is attributed to the dissociation of four protons. (From the plot of absorbances given in the paper, the present author has the impression that the four protons are not dissociated at exactly the same pH value.)... 

Besides the azo coupling reactions of 1-methyl- and 2,5-dimethylpyrrole with benzenediazonium-4-sulfonate mentioned above, Butler et al. (1977) synthesized almost all possible combination products of the unsubstituted and four 4-substituted benzenediazonium ions with pyrrole itself, with most isomeric mono-, di-, and trimethyl-pyrroles, and with 3-ethyl-2,4-dimethylpyrrole. These authors also investigated the kinetics of all these combinations (see Sec. 12.7). 

Fig. 12-4. Rate of azo coupling of benzenediazonium-4-sulfonate with salicylic acid as a function of pH (Bagal et al., 1985).

Benzenediazonium-4-sulfonate, 2193 Benzenediazonium tetrachlorozincate, 3476 Benzenediazonium tribromide, 2227... 

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