Bezzubets, M. K.; Rozina, V. S. published the artcile< Acidic derivatives of anthraquinone. I. Influence of substituents in the phenylamine radical of anthraquinone derivatives on their properties>, Category: esters-buliding-blocks, the main research area is .
Substitution of Br by PhNH in 1-amino-4-bromo-2-anthraquinonesulfonic acid (I) leads to a change of the orange color to blue (bathochromic effect); substitution within the PhNH group gives either a batho- or hypsochromic effect, insufficient, however, to change the visible color range, with Me giving the 1st effect and Cl giving the 2nd; their shift from the 4-position to the 2-position produces a hypsochromic effect. Stability of the dyes is improved by Me or Cl substitution in the PhNH group, with Cl giving the best effect; analogously, the solubility of Na salts drops. I (10 g., Na salt) in 200 ml. H2O and 16 ml. EtOH was heated 4 hrs. at 95° with 9.3 g. PhNH2, 5 g. Na2CO3, and 1 g. CuSO4, and, after steam distillation, the precipitated product was washed and recrystallized in the form of its Na salt, yielding 70% Na 1-amino-4-phenylamino-2-anthraquinonesulfonate, absorption maximum 605 mμ. o-Toluidine gave the corresponding 2′-Me derivative (75%), absorption maximum 610 mμ, while the 4′-analog had a maximum at 615 mμ. 2,4-Me2C6H3NH2 gave 65% of the 2′,4′-di-Me analog, maximum 620 mμ, while 2,4,5-Me3C6H2NH2 gave 73% of the 2′,4′,5′-tri-Me analog, maximum 630 mμ. 4-ClC6H4NH2 (9.6 g.) in 80 ml. H2O and 40 ml. EtOH was treated at 80-5° with 5 g. NaHCO3, 0.5 g. CuCl, and 10 g. I (Na salt) and refluxed 9 hrs.; after steam distillation the cooled filtrate yielded 64% Na 1-amino-4-(4-chlorophenylamino)-2-anthraquinonesulfonate (recrystallized from water), maximum 600 mμ; 2-ClC6H4NH2 gave 46% of the 2′-chloro analog, maximum 585 mμ; 2,5-Cl2C6H3NH2 gave 45% (after 25 hrs.’ reaction) of the 2,5′-di-Cl analog, maximum 580 mμ; the 3′,5′-di-Cl analog was similar; the 3,4,5-Cl3C6H2NH2 (I) gave 50% of the 3′,4′,5′-tri-Cl analog, maximum 575 mμ. Preparation of I: 50 g. p-nitroaniline in 300 ml. HCl and 150 ml. AcOH was chlorinated at 0°, yielding 78-80% 2,6,4-Cl2(O2N)C6H2NH2, m. 188.5-89° (from EtOH-AcOH); this (12 g.), diazotized, added at 90-5° to 300 ml. HCl and 30 g. CuCl paste, kept 1 hr. at 90°, and cooled, gave 3,4,5-trichloronitrobenzene (55%), m. 68-9° (from dilute AcOH); this (6.8 g.) added to hot 30 ml. H2O, 10 g. Fe shavings, and 1 ml. 40% AcOH, followed by steam distillation, gave I, m. 95-6°.
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) published new progress about Dyes. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Category: esters-buliding-blocks.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics