P-Aminobenzenesulfonic acid

Problem 21.9 (a) Why does sulfanilic (p-aminobenzenesulfonic) acid exist as a dipolar ion, while p-aminobenzoic acid does not (b) Why is sulfanilic acid soluble in bases but not in acids -4... 

The influence of the sulfonic acid group upon the course of ethanol deaminations somewhat resembles that of the methyl group. Thus, o-aminobenzenesulfonic acid gives only the ether 18 the meta isomer yields a mixture of m-ethoxybenzenesulfonic acid and benzenesulfonic acid (the ether predominates) 18> 19 and from p-aminobenzenesulfonic acid the only product isolated is benzenesulfonic acid.20... 

Problem 36.3 Account for the fact that p-aminobenzoic acid or < -aminobenzoic acid does not exist appreciably as the dipolar ion, but p-aminobenzenesulfonic acid sulfanilic acid) does. Hint What is Kb for most aromatic amines )... 

Aromatic monoamines, having a minimum one additional functional group, and being found in the patent literature of poly(ester-imide)s, are the aforementioned p-aminobenzoic acid [48, 77], the p-aminophenol [78], the aminoth-erephthalic acid [79] and the p-aminobenzenesulfonic acid [80], but probably none of these monomers were ever used for large scale production. Also the di-aminobenzenes had no economical success as wire enamel raw materials, probably because they were too expensive, too toxic and because they have, in bulk, insufficient storage stability. 3,5-Diaminotriazole-(l,2,4) was claimed as raw material for wire enamel resin yielding films with improved hardness [81]. 

AMINOBENZENESULFONIC ACID or p-AMINOBENZENESULFONIC ACID (121-57-3) CsH NOjS HjO Decomposes on contact with strong acids, forming sulfur trioxide. The aqueous solution is acidic reaction with strong bases. Incompatible with alkylene oxides, aliphatic amines, alkanolamines, amides, ammonia, epichlorohydrin, organic anhydrides, isocyanates, oxidizers, vinyl acetate. On small fires, use dry chemical powder (such as Purple-K-Powder), Halon , water spray, or CO2 extinguishers. 

AI3-15414 Aniline-4-sulfonic acid Aniline-p-sulfonic acid Aniline-p-sulphonic acid Benzenesulfonic acid, 4-amino- CCRIS 4576 EINECS 204482-5 HSDB 5590 Kyselina sulfanilova NSC 7170 p-Aminobenzenesulfonic acid Sulfanilic acid Sulfanilsaure Sulphanilic acid. Used in dyestuffs, organic synthesis, medicine. 

PROBLEM 11.22 Methyl orange is an azo dye used as an indicator in acid-base titrations. (It is yellow-orange above pH 4.5 and red below pH 3.) Show how it can be synthesized from p-aminobenzenesulfonic acid (sulfanilic acid) and N,N-dimethylaniline. 

Outline a synthesis of orange II from 2-naphthoI and p-aminobenzenesulfonic acid. 

Derivatization with p-aminobenzenesulfonic acid/N(l-naphthyl) ethylenediamine dihydrochloride... 

Li X, Wan Y, Sun C (2004) Covalent modification of a glassy carbon surface by electrochemical oxidation of p-aminobenzenesulfonic acid in aqueous solution. J Electroanal Chem 569 79-87... 

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