Aniline-o-sulfonic acid

CAS 88-21-1 EINECS/ELINCS 201-810-9 Synonyms o-Aminobenzene sulfonic acid o-Aminophenylsulfonic acid Aniline-2-sulfonic acid Aniline-o-sulfonic acid Anilino-2-sulfonic acid... 

Aniline-3-sulfonic acid. See Metanilic acid Aniline-4-sulfonic acid. See Sulfanilic acid m-Anilinesulfonic acid. See Metanilic acid Aniline-o-sulfonic acid. See 2-Ami nobenzene sulfonic acid... 

Red Lake P n Made by coupling diazotized p-nitro aniline-o-sulfonic acid with jS-naphthol. 

Self-doped polyaniline nanofibers have been synthesized recently by Yang et al. [249] via a self-assembly process using the self-doped monomer (o-aminobenzenesulfonic acid) and aniline. It was suggested that the sulfonated monomer (o-aminobenzenesulfonic acid) plays a dual role as a monomer and a surfactant in the nanofiber formation. The nanofibers were synthesized chemically using different molar ratios of aniline/o-aminobenzenesulfonic acid without an external dopant. It was proposed that the o-aminobenzenesulfonic acid and anilinium cations form micelles in aqueous solution, which further act as templates to form nanofibers. Self-doped polyaniline nanofibers with an average diameter of 370 nm synthesized using an aniline/o-aminobenzenesulfonic acid... 

Fig. 5. Direct red dyes, (a) Direct Red 81 described ia text (68) (b) Direct Red 2 (o-toLidiae coupled to two moles of naphthionic acid) (69) (c) Direct Red 23 (aniline coupled to 6,6 -ureylenebis-l-naplitliol-3-sulfonic acid with a second coupling with j aminoacetanilide) (70) and Direct Red 80 (2 mol 6-amino-3,4 -azobenzenedisulfonic acid coupled twice to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid) (73). Direct Red 24 (4-aniino-y -toluenesulfonic acid coupled under acidic conditions to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid followed by an alkaline coupling of o-anisidine) (71) (d) Direct Red 72 (Broenner s acid, ie, 6-artiino-2-naphthalenesulfonic acid coupled under acidic conditions to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid followed by an...

The same authors studied the CL of 4,4,-[oxalylbis(trifluoromethylsulfo-nyl)imino]to[4-methylmorphilinium trifluoromethane sulfonate] (METQ) with hydrogen peroxide and a fluorophor in the presence of a, p, y, and heptakis 2,6-di-O-methyl P-cyclodextrin [66], The fluorophors studied were rhodamine B (RH B), 8-aniline-l-naphthalene sulfonic acid (ANS), potassium 2-p-toluidinylnaph-thalene-6-sulfonate (TNS), and fluorescein. It was found that TNS, ANS, and fluorescein show CL intensity enhancement in all cyclodextrins, while the CL of rhodamine B is enhanced in a- and y-cyclodextrin and reduced in P-cyclodextrin medium. The enhancement factors were found in the range of 1.4 for rhodamine B in a-cyclodextrin and 300 for TNS in heptakis 2,6-di-O-methyl P-cyclodextrin. The authors conclude that this enhancement could be attributed to increases in reaction rate, excitation efficiency, and fluorescence efficiency of the emitting species. Inclusion of a reaction intermediate and fluorophore in the cyclodextrin cavity is proposed as one possible mechanism for the observed enhancement. 

Other common intermediates for azo pigment production are 2,4-dinitro-aniline, acetoacet-o-chloroanilide, acetoacet-o-toluidide, phenyl- and p-tolyl-methylpyrazolone, 2-hydroxy-3-naphthoic acid, Naphtol AS and its derivatives, and 2-chloro-4-aminotoluene-5-sulfonic acid. 

Recent work reports the incorporation of aniline sulfonic acid derivatives, o- and m-aminobenzenesulfonic denoted as 1 and 11, respectively, 3-amino-4-methoxybenzenesulfonic (HI), 3-aniline-1-propane sulfonic acid (IV), and... 

Fig. 23 ESR spectra of Cu2Cr/aniline sulfonic acid derivatives after a thermal treatment at 200 °C for 4h in air recorded at 105 K with a sweep width of a 6500 G b 150 G. H(I) o-aminobenzenesulfonic acid H(I) m-aminobenzenesulfonic acid H(III) ...

In a 3-I. round-bottom flask fitted with a reflux condenser are placed 218 g. (1 mole) of coarsely powdered technical o-nitro-aniline-/>-sulfonic acid, and a hot mixture of 775 cc. of concentrated sulfuric acid (sp. gr. 1.84) and 950 cc. of water (Note 1). Heat is applied and the mixture is refluxed gently for. an hour after solution is practically complete (total about three hours). The resulting dark solution is allowed to cool and is poured slowly into 12 1. of cold water in a crock (Note 2). 

Reduction of 2-nitrochIorobenzene-4-sulfonic acid gives o-chlorometanilic acid which is used in making azo dyes. The real technical value of nitrochlorobenzene-sulfonic acid, however, lies in the ability of its chlorine atom to be replaced by various groups. For example, o-nitrophenol-p-sulfonic acid is obtained by treatment wiui sodium hydroxide, and this product, on reduction, yields o-aminophenol-p-sulfonic acid. An ogously, nitrochlorobenzenesulfonic acid gives o-nitroanisole-p-sulfonic acid by treatment with alcoholic methanol, and from this is obtained o-anisidine-p-sulfonic acid. The action of ammonia on nitrochlorobenzenesulfonic acid produces o-nitroaniline-p>sulfonic acid aniline and its derivatives produce o-nitrodiphenylamine-p Sulfonic acids (cf. Table II). 

Beller and coworkers recently reported a new strategy for the synthesis of poly-substituted anilines based on a three-component-coupling reaction and a domino deprotec-tion/aromatization reaction (equation l)44. A mixture of O-benzyl carbamate, p-toluene-sulfonic acid, aldehyde, AC2O and dienophile in /V-rnclhy I pyrrol idone was allowed to react for 24 h at 120 °C, followed by Pd/C catalyzed dehydrogenation in triglyme at 140 °C. A variety of tri-, tetra- and penta-substituted anilines were efficiently created by this domino process. 

On bromination of o- or /7-hydroxy- or o- or /7-amino-benzoic acid, or the corresponding sulfonic acids, even at room temperature, bromine replaces the COOH or S03H group with liberation of C02 or H2S04 as the case may be. At 40-45° the CHO group of o- or /7-hydroxy- or o- or /7-aminobenzaldehyde is also replaced by bromine, with evolution of CO. The end products are 2,4,6-tribromo-phenol or -aniline.460 Thus /7-hydroxybenzoic and sulfanilic acid, for example, can be determined quantitatively by means of O.lN-bromide-bromate solution. 

The optimum temperature for simple arylamines is 0-2°, for m-haloaryl-amines 0-5°, and for benzidines, naphthylamines, and o- and / -haloarylamines 10-12°. In isolated cases higher temperatures are used, e.g., 34° for / -nitro-aniline and 40° for o-anisidine. The end-point of the reaction is determined by testing for an excess of nitrous acid with potassium iodide-starch paper. Amino sulfonic acids are no longer used to remove the excess of nitrous acid since they react with reactive diazo compounds.244... 

PNMA, poly(N-methylaniline) PANI, poly(aniline) PEDOT, poly(3,4-ethylenedioxythiphene PSS, poly(styrene-sulfonate), PPy, poly(pyrrole) PEO, poly(ethylene oxide) DBSA, dodecylbenzene sulfonic acid CSA, camphor sulfonic acid PTSA, poly(o-toluene sulfonic acid) PFOA, perfluoro-octanolc acid TSA, toluene sulfonic acid CNF, carbon nanofiber SWCNT, single-walled carbon nanotube NP, nanoparticle MWCNT, multiwalled carbon nanotube PTh, poly(thlphene) CNT, carbon nanotube POA, poly(o-anisidine) SPANI, poly(anilinesulfonlcacld) PB, Prussian Blue DAB, 1,2-diamino benzene POEA, poly(o-ethoxyanlllne) PMMA, poly(methyl methacrylate). 

Ammonium acetate Aniline Benzanthrone Bromine Carmine (Coccus cacti) Carminic acid 2-Chlorophenol Crystal violet lactone Diaminodiphenic acid Di-n-amylamine Diazoaminobenzene o,a-Dichlorotoluene Dimethoxypropane 4-Dimethylaminoazobenzene-4-sulfonic acid, sodium salt p-Dimethylaminobenzaldehyde 4-Dimethylaminobenzene 6-Dimethylaminophenylazobenzothiazole N,N-Dimethylaniline Dinitrotoluene 2,4-Dinitrotoluene Direct blue 8 Direct blue 10 Direct blue 25 Direct blue 218 Direct orange 6 Direct violet 32 Disperse blue 7 Disperse red 60 Dodecene-1 N-(p-Ethoxycarbonylphenyl)-N -ethyl-N -phenylformamidine Ethylene cyanohydrin Ethylene thiourea... 

Films prepared in a similar manner with Hydrin C are those utilizing poly(N,N -dimethyl-2,2 -bipyrrole) [220], and polypyrrole [221]. Electrochromic films of Hydrin C and poly(o-methoxyaniline) have also been produced in which the aniline polymer is chemically polymerized in the presence of p-toluene sulfonic acid and blended with Hydrin C with the blend cast from solution [219]. Another example in which an electrochromic polymer was electrochemically polymerized in the presence of an insulating polymer is that of polypyrrole-polyjether urethane) or polypyrrole-poly(ethylene-co-vinyl alcohol) composite films [222]. Both films switched between a yellow reduced state to a bluish brown oxidized state, similar to polypyrrole. 

Finally, we mention some other attempts that have been directed toward the preparation of copolymers poly(aniline-co-o//w-toluidine) [732, 733], poly(aniline-cothiophene) [734], poly(aniline-co-aniline with sulfonate, alkylsulfonate, carboxy-late, chloro and fluoro groups) [735], poly(aniline-co-/7-phenylene diamine) [737], poly(aniline-co-w-phenylenediamine) [736, 738], poly(aniline-co-diphenyl-amine) [164,360,739], poly(aniline-co-dithioaniline [740], as well as copolymers of diphenylamine and anthranilic acid [361] or benzidine [349], iV-vinylcarbazole and thienylpyrrole and terthiophenes [618], and aniline with aminonaphthalenesul-fonates [243]. Several other works that describe copolymers can be found among... 

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