Nitrobenzene Nitrobenzoic acid

Schmidt, Brown and D. Williams [40] examined the nuclear magnetic resonance of 14N in three aromatic nitro compounds nitrobenzene, nitrobenzoic acid, di-nitrobenzoyl chloride. 

Most studies in the microbial metabolism of nitroaromatic compounds used aerobic microorganisms. In most cases no mineralization of nitroaromatics occurs, and only superficial modifications of the structures are reported. However, under anaerobic sulfate-reducing conditions, the nitroaromatic compounds reportedly undergo a series of reductions with the formation of amino compounds. For example, trinitrotoluene under sulfate-reducing conditions is reduced to triaminotoluene by the enzyme nitrite reductase, which is commonly found in many Desulfovibrio spp. The removal of ammonia from triaminotoluene is achieved by reductive deamination catalyzed by the enzyme reductive deaminase, with the production of ammonia and toluene. Some sulfate reducers can metabolize toluene to (X) sub 2. Similar metabolic processes could be applied to other nitroaromatic compounds like nitrobenzene, nitrobenzoic acids, nitrophenols, and aniline. Many methanogenic bacteria can reduce nitroaromatic compounds to amino compounds. 

De la Mare and Hilton198 measured the rates at 25 °C of bromination of benzene, benzoic acid, phthalic acid, 2-nitrobenzoic acid, trimethylanilinium perchlorate and nitrobenzene by hypobromous acid with sulphuric or perchloric acids as catalysts, in some cases in aqueous dioxan, in an attempt to discover if Br+ or H2OBr+ was the appropriate brominating species since the logarithm of the rates should then follow the acidity functions H0 or HR (J0) respectively. The results, however, were inconclusive and relative rates of bromination were determined (see Table 53). 

It is noteworthy that, although 4-bromoanisole produces anisic acid in high yield, 4-hydroxybenzoic acid is isolated in only 17% yield from the corresponding reaction of 4-bromophenol. Also, 4-bromoacetophenone, which may react by a normal SN reaction, is readily converted into 4-acetylbenzoic acid, whereas 4-bromonitro-benzene produces 4-nitrobenzoic acid in only 17% yield, together with nitrobenzene (17%). 

CASRN 15457-05-3 molecular formula C13H7F3N2O5 FW 328.20 Chemical/Physical. When fluorodifen as an aqueous suspension was irradiated using UV light (A, = 300 nm), 4-nitrophenol and 4-(trifluoromethyl)-2-aminophenol formed as the major products (>90% of total product formation). In addition, 4-(trifluoromethyl)-2-nitrophenol formed as a minor product (<1%) as well as 4-hydroxy-3-nitrobenzoic acid. In methanol, photolysis of fluorodifen yielded 4-nitrophenol and 2-amino-4-(trifluoromethyl)anisole. In cyclohexanone, 4-nitrophenol and 3-(trifluoromethyl)nitrobenzene were formed (Ruzo et al., 1980). 

Nitrotoluenes are considered to be toxic substances, though their toxicity is considerably lower than that of nitrobenzene. It has been suggested that this should be ascribed to the ease with which nitrotoluene is oxidized in the human body to nitrobenzoic acid, which is only slightly toxic. 

Smith and Lieber (36) reported that, although the use of alkali activated Raney nickel for the hydrogenation of carbonyl groups, it had a deterring effect on the reduction of aromatic nitro compounds. In particular, alkali retarded the reduction of nitrobenzene and the three isomeric sodium nitrobenzoates, whereas it increased the velocity of reduction of the methyl and ethyl esters of nitrobenzoic acid. 

Suggest syntheses of the following compounds from the starting material given (a) 4-chloro-3-nitrobenzoic acid from toluene (b) 2-chloro-4-nitrobenzoic acid from toluene (c) 4-benzylbenzoie acid from toluene (d) l-ethyl-3-nitrobenzene from benzene e) iso butyl benzene from benzene. 

C7H6CIN02 4-chloro-2-methyl-1-nitrobenzene 5367-28-2 40.00 1 3576 2 10368 C7H6N204 2-amino-3-nitrobenzoic acid 606-18-8 15.00 1.5580 1... 

Trifluoroacetic nitrate, prepared in situ from ammonium nitrate and trifluoroacetic anhydride, has been used for nitration of aromatic compounds at room temperature with high yields. While benzoic acid gives m-nitrobenzoic acid nearly quantitatively, nitrobenzene is not reactive under these conditions. Attack at the ortho position rather than the para position is observed with activated benzene derivatives like anisole. However, this system oxidizes phenols to quinoid products. ... 

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