Synthesis of 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene was written by Griffith, R. H.;Hope, Edward. And the article was included in Journal of the Chemical Society, Transactions in 1925.HPLC of Formula: 169045-04-9 This article mentions the following:
5-Bromo-2-acetylamino-p-tolyl Me ether (I), m. 191°; hydrolysis with concentrated HCl gives the amine, m. 100° (Bz derivative, m. 159°); the azo dye with β-C10H7OH, red needles with green luster, m. 210°. Diazotized and reduced with SnCl4, the amine gives a hydrazine, pale brown, m. 192°, which, on treatment with CuSO4 and oxidation with alk. KMnO4, yields 3-bromoanisic acid, m. 217-8°. Since the 2-Br derivative is recorded as m. 212°, it was synthesized from 2-bromo-p-tolyl Me ether, b16 114° b760 222°, and found to m. 199°. Oxidation of I with KMnO4 in the presence of MgSO4 gives about 70% of 5-bromo-2-acetylamino-4-methoxybenzoic acid, m. 253°; hydrolysis with concentrated HCl gives 4-bromo-m-anisidine, m. 90.5° (Bz derivative m. 124°); hydrolysis with alkali gives 5-bromo-2-amino-4-methoxy-benzoic acid, pale brown, m. 201°, decomposed 213° (Na salt, long needles; Cu salt, green). Diazotized, treated with Na2S2 and boiled with Zn dust in Na2CO3 solution, it yields 5-bromo-4-methoxy-2-thiolbenzoic acid, which, because of its ease of oxidation, is used as the Na salt in the condensation with ClCH2CO2H, forming 4-bromo-2-carboxy-5-methoxy-phenylthiolacetic acid (II), pale brown, m. 243° (decomposition). Heated with AcONa and Ac2O, dissolved in 3% alkali and treated with K3Fe(CN)6, it gives 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene (III), dark red, m. 355-60°; the dye is reprecipitated from its deep blue solution in concentrated H2SO4 in a gelatinous state very suitable for the preparation of the vat, which is pale yellow and dyes cloth a good scarlet. The PhNO2 solution shows an absorption band with a maximum at λ = 529; “Helindone Fast Scarlet R” shows a similar band with a maximum at λ = 520. II and isatin give the compound C17H10O3N-BrS (IV), which has a much bluer shade than III; its H2SO4 solution is purple but its dyeing properties are unsatisfactory, probably on account of further reaction during reduction. II and acenaphthenequinone give an orange powder (V), m. 337°, giving dark brown solutions in concentrated H2SO4 and dyeing cloth a good orange from a bright blue bath. In the experiment, the researchers used many compounds, for example, 2-Amino-5-bromo-4-methoxybenzoic acid (cas: 169045-04-9HPLC of Formula: 169045-04-9).
2-Amino-5-bromo-4-methoxybenzoic acid (cas: 169045-04-9) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. HPLC of Formula: 169045-04-9
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary