Anthraquinones bromo

Among anthraquiaoae dyes (see Dyes, anthraquinone). Acid Blue 78 [6424-75-5] C2 H25BrN20 S -Na, or Alizarin Pure Blue B, is a wool dye. Bromamine acid [116-81-4] (l-amiao-4-bromoanthraquiaoae-2-sulfonic acid), C24HgBrNO S, is a useful dye iatermediate. A number of bromo anthraquiaoae, pyrathroae, and benzanthrone dyes are known. 

Fig. 1.11 Dissociation ranges of colour indicators for determination of the acidity function H0 in H2S04-H20 mixtures (1) p-nitroaniline, (2) o-nitroaniline, (3) p-chloro-o-nitroaniline, (4) p-nitrodiphenylamine, (5) 2,4-dichloro-6-nitroaniline, (6) p-nitroazobenzene, (7) 2,6-dinitro-4-methylaniline, (8) benzalacetophenone, (9) 6-bromo-2,4-dinitroaniline, (10) anthraquinone, (11) 2,4,6-trinitroaniline. (According to L. P. Hammett and A. J. Deyrup)...

Complete deoxygenation of quinones to hydrocarbons is accomplished in yields of 80-85% by heating with a mixture of zinc, zinc chloride and sodium chloride at 210-280° [932]. Refluxing with stannous chloride in acetic and hydrochloric acid followed by refluxing with zinc dust and 2 N sodium hydroxide reduced 4 -bromobenzo[5. 6 1.2]anthraquinone to 4 -bromo-benzo[5. 6 1.2]anthracene in 95% yield [181], and heating with iodine, phosphorus and 47% hydriodic acid at 140° converted 2-chloroanthraquinone to 2-chloroanthracene in 75% yield [222]. Also aluminum in dilute sulfuric add can be used for reductions of the same kind [151]. 

The following unimportant preparative methods may be mentioned the production of /3-methyl anthraquinone by the reduction of 2-bromo-3-methyl anthraquinone 7 the oxidation of /3-methyl anthracene-7-carboxylic acid 8 and the reduction of 2-methyl anthraquinonyl-i-diazonium sulfate.9... 

Anthraquinones with electron-donating substituents, such as amino or hydroxyl groups, permit selective halogenation of one or the other nucleus by appropriate choice of reaction conditions. Only the chloro and bromo derivatives are commercial products. 

SYNS ANTHRAQUINONE, 2-BROMO-l,5-DIAMINO-4,8-DIHYDROXY- MODR OSTACETOVA LR... 

SYNS 9,10-ANTHRACENEDIONE, l-BROMO-4-(METHYLAMINO)- ANTHRAQUINONE, l-BROMO-4-(METHYLAMINO)- l-METHYLAMINO-4-BROMANTHRACHINON l-(METHYLAMINO)-4-BROMOANTHRAQUINONE... 

The intramolecular condensation of o-aroylbenzoic acids in the presence of concentrated sulfuric acid gives substituted anthraquinones. The acid strength, reaction temperature, and period of heating are carefully controlled to insure optimum yields and to avoid sulfonation products. Boric acid has been added as a sulfonation inhibitor. Substitution in the para position of the aroyl group leads to 2-alkyl-, 2-chloro-, and 2-bromo-anthraquinones. ... 

Cl5H10BrNO2 1-bromo-4-(methylamino)anthraquinone 128-93-8 25.00 1.5215 2 28125 C15H11N303 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodia 146-22-5 25.00 1.3617 2... 

Methylaminoanthraquinone has been prepared from 1-chloro-, 1-bromo-, and 1-nitroanthraquinone by treatment with alcoholic methylamine under pressure from 1-methoxy- and 1-phenoxyanthraquinone with methylamine in pyridine solution at 150° from potassium anthraquinone-1-sulfonate with aqueous methylamine at 150-160° from 1-aminoanthraquinone by treatment with formaldehyde, or methyl alcohol in sulfuric acid or oleum and by hydrolysis of />-toluenesulfonyl-methylaminoanthraquinone with sulfuric acid. ... 

METHYL AMINO-4-BROMOAWTHRAQUINONE (Anthraquinone, l-methylamino-4-bromo-)... 

HDPE, 231J, control 925 HDPE + TiO2 (2.3%) 6U HDPE + anthraquinone 385 HDPE + anthrone 20 HDPE + benzanthrone 20 HDPE + 2-methylanthraquinone 50 HDPE + 1,3,5-triacetylbenzene 50 HDPE + a-bromo- -phenylacetophenone 75 HDPE + 9-fluorenone-U-carboxylic acid 575 HDPE + flavone 650... 

The formation of fused anthraquinone systems in a two-stage photoreaction between 2-bromo-3-methoxy-1,4-naphthoquinone and 1,1-diarylethylenes is well established, and the reaction has been extended to include 1-(heteroaryl)-1-phenylethylenes (e.g., 149). In general the preferred mode of ring-closure follows... 

A soln. of 2-methoxy-3 bromo-1,4-naphthoquinone and 1,1-diphenylethylene in benzene irradiated with a 300 w. high-pressure Hg-arc lamp -> 5-phenyl-7,12-benz[a]anthraquinone. Y 61%. F. e. s. K. Maruyama and T. Otsuki, Chem. Lett. 1975,87. 

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