Petrovich, P I’s team published research in Zhurnal Obshchei Khimii in 1960 | 16426-64-5

Zhurnal Obshchei Khimii published new progress about Nitration. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, HPLC of Formula: 16426-64-5.

Petrovich, P. I. published the artcile< Oxidative nitration of aromatic compounds. IV. Mercury compounds of some p-disubstituted benzenes and their reaction with nitric acid>, HPLC of Formula: 16426-64-5, the main research area is .

Heating 200 g. p-C6H4Cl2, 40 g. Hg(OAc)2, 60 ml. AcOH, and 1 ml. petr. ether 11.5 hrs. at 125° gave 50% acetoxymercuri-p-dichlorobenzene (I) m. 168.5-9.2°, along with bis(2,5-dichlorophenyl)mercury (II), m. 235-7°. The former with NaCl gave the chloromercuri analog, m. 207-7.5°. Similar reaction of 100 g. p-C6H4Cl2 and 20 g. Hg(OAc)2 in AcOH in the presence of petr. ether in 13 hrs. gave a moderate yield of II, which was also formed by heating I in boiling xylene 10 hrs. I heated without solvent at 172° gave p-C6H4Cl2. II heated with HgCl2 in EtOH-C6H6 gave chloromercuri-p-dichlorobenzene. Oxidation of chloromercuri-p-xylene with KMnO4 in aqueous NaOH at 95° gave 85.3% anhydro-2-(hydroxymercuri)terephthalic acid (Whitmore and Isenhour, CA 23, 4943), which with Br-KBr gave bromoterephthalic acid, m. 298-8.7°. Diazotization of 4-nitro-2-aminotoluene and treatment with HgCl2 gave a colorless 2:1 complex of 4-nitro-2-toluenediazonium chloride and HgCl2, which on conventional decomposition gave 38.8% 2-chloromercuri-4-nitrotoluene, m. 231.5-2°, which with powd. Cu in NH4OH gave bis(4-nitro-2-tolyl)mercury, m. 258.2-8.6°, while oxidation of the former with KMnO4 gave 75% anhydro-2-(hydroxymercuri)-4-nitrobenzoic acid (Whitmore and Middleton, CA 16, 2856), which with Br-KBr gave 2-bromo-4-nitrobenzoic acid, m. 167-8°. I added gradually to 58% HNO3 at 75° and stirred 1.2 hrs. (N oxide formation was caused by gradual addition of paraformaldehyde) gave some 2,5-dichloronitrobenzene (III) and a low yield of 3,6-dichloro-2,4-dinitrophenol (IV), m. 146.2-7°. Similar treatment of II also gave the same product in low yield. Heating 36 g. p-C6H4Cl2, 276 ml. 58% HNO3, 36 g. Hg(NO3)2, 1.2 g. NaNO2, and 1 ml. petr. ether 25 hrs. at 80° gave low yields of III and IV. The above reaction mixture heated in a sealed tube 7 hrs. at 140° (petr. ether omitted) gave HgCl2, 2,5-dichloro-1,3-dinitrobenzene, 2,5-dichloro-1,4-dinitrobenzene and, as the principal product, III (yield not stated). Heating anhydro-2-(hydroxymercuri)terephthalic acid with 58% HNO3 and a trace of NaNO2 (as above) 7 hrs. at 80° in a sealed tube gave 30% nitroterephthalic acid, m. 267-8°. Heating 2-chloromercuri-4-nitrotoluene with 58% HNO3 2.5 hrs. at 50° in the presence of NaNO2 gave a little 2-nitroso-4-nitrotoluene and 2,4-(O2N)2C6H3Me.

Zhurnal Obshchei Khimii published new progress about Nitration. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, HPLC of Formula: 16426-64-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary