P-Aminophenylarsinic acid

SYNS p-AMINOBENZENEARSONIC ACID 4-AMINOBENZENEARSONIC ACID AMINO-PHENYLARSINE ACID p-AMINOPHENYLARSINE ACID p-AMINOPHENYLARSINIC ACID 4-AMINOPHENYLARSONIC ACID p-ANILINE-ARSONIC ACID ANTOXYLIC ACID p-ARSANIL-IC ACID 4-ARSANILIC ACID ATOXYLIC ACID... 

AMINOPHENYLARSINE ACID see ARA250 p-AMINOPHENYLARSINE ACID see ARA250 p-AMINOPHENYLARSINE OXIDE DIHYDRATE see ALVIOO... 

The N-acyl and N-alkyl derivatives of aminoarylarsinic acids are prepared by the usual methods. Acetyl-jp-aminophenylarsinic acid, in addition to the usual method of acetylation of the arsinic acid, may be formed by subjecting p-aminoacetanilide to the Bart-Schmidt reaction. An interesting series of N-aryl derivatives of p-aminophenylarsinic acid has been obtained by King and his co-workers in the course of seeking organic arsenicals of therapeutic value. ... 

Benzoyl-p-aminophenylarsinie acid was first described in 1906, and prepared by the benzoylation of sodium p-aminophenylarsinatc, using benzoyl chloride and aqueous sodium hydroxide. Replacing the benzoyl chloride by o-, m- or p-nitrobenzoyl chloride. King isolated o -, m -, and p -mononitrobenzoyl-p-aminophenylarsinic acids respectively, which in turn were reduced to the corresponding amino-compounds in yields of 60 to 86 per cent. ... 

By the condensation of p-aminophenylarsinic acid with m-nitrobenzene-sulphonyl chloride or m-nitro-p-toluenesulphonyl chloride, compounds of type I are obtained, where R is H or CHj. Tliese on further nitration yield type II ... 

The measurements of crystals of p-aminophenylarsinic acid and its salts are as follows ... 

Oxalyl - p - aminophenylarsinic acid, COaH.CO.NH-CgHgAsO (011)2. — mixture of 347 grams of sodium p-arsanilate and 378 grams of crystallised oxalic acid are heated at a temperature of 120° to 180° C. until the bulk of the water is driven off, the temperature then being slowly raised to 160° C., until the mass becomes pulverulent. After cooling, it is mixed with 3000 e.c. of water, 390 c.c. of hydrochloric acid (density 1 12) are added and the mixture stirred for thirty minutes. The crude product is dissolved in 700 c.c. of cold water and 200 c.c. of 7N sodium hydroxide, the filtered solution being treated with 890 c.c. of hydrochloric acid (density 1 12) to precipitate the oxalyl derivative. The latter is a white powder, unmelted at 860° C., soluble in hot water, alkali hydroxide and carbonate, insoluble in acids and sparingly soluble in methyl alcohol. 

The siftn.-carbamides of the following arsinic acids have also been prepared m -aminohenzoyl-o -aminohenzoyl-p-a7ninophenylarsinic acid, o"-am,inobemoyl-m -atninobenzoyl-p a7ninophenylarsinic acid, and o"-aminobenzoyl-o -aminobenzoyl-p-aminophenylarsinic acid. 

Arsinic Acids containing -the Glyoxaline Nucletis. Glyoxaline-4 (or 5 )-carboxy-p-aminophenylarsinic acid, ... 

A number of azo-dyes have been prepared recently, and these are given in Table III. of the Appendix diazoamino derivatives of p-aminophenylarsinic acid are given in Table IV. Derivatives obtained from diazotised arsanilie acid and hydroxy- and amino-quinolines are given in Table V. ... 

Diazotised benzidine is coupled with 8-amino-a-naphtliol-8 C-disulphonic acid (H acid) in acid solution and the resulting dyestuff in sodium carbonate solution added to diazotised p-aminophenylarsinic acid. The resulting trisazo-dyestuffis a brownish-black powder, soluble in water, giving a blue solution, which dyes cotton directly in blue tones. 

Diazotised p-aminophenylarsinic acid is coupled with H acid in alkaline solution and the brownish-violet product cooled and stirred with diazotised diehlorobenzidine. The resultant dyestuff is a glistening dark brown powder, ginng a deep blue solution in water. In place of benzidine or diehlorobenzidine the following may be used tolidine, dianisi-dine, or diaminophenyl urea. Instead of H acid, S-amino-5-naphthol-7-sulphonic acid (J acid), 1 8-aminonaphthol-4-sulphonie acid (S acid or 1 8-dihydroxynaphthalene-8 6-di.sulphonie acid (chronio trope acid) may be employed. 

A series of aminoarsinic acids may be obtained by the condensation of a-halogeiiaeylamides of the composition X.CHR.CO.NRiR (where X=halogen, R=alkyl, aryl, or hydhogen, Rj, R2=alkyl, aryl, substituted aryl, or hydrogen) with p-aminophenylarsinic acid, its homologues, substituted derivatives or salts of these acids. ... 

Carboxymethylenethiophenyl-4-arsinicacid,C02H.CH2.S.CgH4. AsO(OH)2.—A diazotised solution of p-aminophenylarsinic acid is added to a solution of potassium xanthate in sodium carbonate at 80 ° C. Sodium hydroxide is then added, and after several hours warming at 90° to 100° C., chloracetic acid and 86 per cent, sodium hydroxide are introduced and tlie solution evaporated to small bulk. The arsinic acid separates on addition of hydrochloric acid. It crystallises from water in pale yellow needles, sintering at 170° C. and melting with decomposition at 187° C. 

When p-aminophenylarsinic acid and an equimolecular quantity of arsinoacetic acid are reduced by sodium hypophosphite in sulphuric acid, most of the amino-acid is reduced to the sulphate of 4 4 -diamino-arsenobenzene, the filtrate on long standing yidding arsenoacetie acid. When the sulphuric acid is replaced by hydrochloric acid, the dihydrochloride of 4 4 -diaminoarsenobenzene, a small quantity of 4-amino-... 

Complex I is jprepared as follows 11 grams of p-aminophenylarsinic acid in 60 c.c. of 5N hydrochloric acid are cooled with 80 grams of ice, diazotised with IdN sodium nitrite solution, the solution filtered, and the filtrate mixed with 60 c.c. of ice-cooled hydrochloric acid (density 1 17). Sulphur dioxide is then passed in, and, after a few minutes, one drop of normal hydriodic acid in 8 c.c. of hydrochloric acid is added as catalyst. A fine, yellow, crystalline precipitate separates out, which after ten minutes is remov, washed with ice-cold hydrochloric acid, followed by acetic acid and ether. The yield is about 12 grams. 

TABLE IV.—DIAZOAMINO-GOMPOUNDS FROM P-AMINOPHENYLARSINIC ACID... 

Mononitrobenzophenone-p-arsinlo aoid, 331. o -Mononitrobenzoyl-p-aminophenylarsinic acid, 198. 

---