Electrochemical reduction of several ortho-substituted nitro-benzenes by controlled potentials was written by Le Guyader, Michel;Tallec, Andre;Legoff, Raymond. And the article was included in Compt. Rend. in 1964.Product Details of 74440-80-5 This article mentions the following:
Nitrobenzenes having an o-halo substituent are reducible, in acid media and with a Hg cathode, to the corresponding amines and hydroxylamines; the latter are capable of Gattermann rearrangement. The following results were obtained [compound reduced, temperature, electrolyte, electrode potential (mv. vs. calomel reference electrode) product obtained, m.p.]: 2-RC6H4NO2 (I) (R = F), <20°, 0.5N H2SO4, -350, 2-RC6H4NHOH (II) (R = F), 90° (petr. ether); I (R = F), 25°, N H2SO4, -900, 2-RC6H4NH2 (III) (R = F), — (Bz derivative m. 110°); I (R = F), 90°, 25% H2SO4, -100, 3,4-R(H2N)C6H3OH (IV) (R = F), — (O,N-di-Bz derivative m. 170°); I(R = Cl), 25°, NH2SO4, -350, II(R = Cl),– (picrate m. 179°); I (R = Cl), 40°, 10% EtOH-N H2SO4, -850, III(R = Cl), — (Bz derivative m. 100°); I (R = Cl), 90°, 25% H2SO4, -100°, IV (R = Cl), 160° (O,N-di-Ac derivative m. 122°); I (R = Br), 20°, 10% EtOH-N H2SO4, -350, II (R = Br), — (HBr salt m. 170°); I (R = Br), 40°, 10% EtOHN H2SO4, -850, III (R = Br), — (Ac derivative m. 96°); I (R = Br), 90°, 50% H2SO4, -100, IV (R = Br), 153° (O,N-di-Ac derivative m. 125°); I (R = iodine), 20°, 50% EtOH-N H2SO4, -350, II (R = iodine), 60° (petr. ether); I (R = iodine), 93°, 20% H2SO4, -150, IV (R = iodine), 150°; 2-O2NC6H4CO2Et (V), 15°, 50% EtOH-N H2SO4, -250, II (R = EtO2C) (VI), 77°; V, 15°, 15% EtOH-N H2SO4, -850, III (R = EtO2C), — (Ac derivative m. 62°); VI, 60°, ≤2N H2SO4, -150, VII, 118°; VI, 80°, ≥5N H2SO4, -150, 2,5-H2N(HO)C6H3CO2H (VIII), 248° (under intermediate conditions, a mixture of VIII and its Et ester, m. 145°, was obtained); 2-O2NC6H4CONH2 (IX), 25°, N H2SO4, -350, VII, 118°; and IX, 25°, N H2SO4, -1100, 2-H2NC6H4CO2H, 145°. In the experiment, the researchers used many compounds, for example, 4-Amino-3-bromophenol (cas: 74440-80-5Product Details of 74440-80-5).
4-Amino-3-bromophenol (cas: 74440-80-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Product Details of 74440-80-5
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary