Oxidation nitrotoluene

Increased 2,6-dinitrotoluene oxidation rate Decreased 2-nitrotoluene oxidation rate... 

The detection of 4-nitrobenzaldehyde and 4-nitrobenzyl alcohol dehydrogenase and 4-nitrotoluene oxygenase activities in 4-nitrobenzoate-grown cells suggests that 4-nitrobenzoate is an inducer of the 4-nitrotoluene degradative pathway. The 4-nitrotoluene oxidation pathway is similar to the pathway for the oxidation of toluene to benzoate as catalyzed by the TOL plasmid upper pathway, which has been shown to be able to deal with 4-nitro substituted substrates (9), however the TOL plasmid pathway is induced by the pathway... 

Oxidation of a side chain by alkaline permanganate. Aromatic hydrocarbons containing side chains may be oxidised to the corresponding acids the results are generally satisfactory for compounds with one side chain e.g., toluene or ethylbenzene -> benzoic acid nitrotoluene -> nitrobenzoic acid) or with two side chains e.g., o-xylene -> phthalic acid). 

The reduction of o-nitrophenyl acetic acids or esters leads to cyclization to oxindoles. Several routes to o-nitrophenylacetic acid derivatives arc available, including nitroarylation of carbanions with o-nitroaryl halides[2l,22] or trif-late[23] and acylation of o-nitrotoluenes with diethyl oxalate followed by oxidation of the resulting 3-(u-nitrophenyl)pyruvate[24 26]. 

The mononitration of toluene results in the formation of a mixture of the ortho, meta, and para isomers of nitrotoluene. The presence of the methyl group on the aromatic ring facilitates the nitration, but it also increases the ease of oxidation. 

The methyl group of -nitrotoluene is activated by the para nitro group. -Nitrotoluene is oxidized to -nitrobenzoic acid [62-23-7] by potassium hexacyanoferrate(III) in alkaline solution, potassium permanganate, or potassium dichromate. -Nitrotoluene is converted to -nitrobenzaldehyde... 

Dinitrotoluene is oxidized to 2,4-dinitrobenzoic acid [610-30-0] by potassium permanganate or chromic acid, and is reduced to 2,4-diaminotoluene by iron and acetic acid. It is reduced partially by zinc chloride and hydrochloric acid to 2-amino-4-nitrotoluene [99-55-8] and by ammonium sulfide to 4-amino-2-nitrotoluene [119-32-4],... 

Self-condensation products of 4-nitrotoluene-2-sulfonic acid or its derivative 4,4 -dinitto-2,2 -stilbenedisulfonic acid or 4,4 -dinitto-2,2 -dibenzyldisulfonic acid [728-42-7] and products of their treatment with teduciag or oxidizing agents. An example is Direct Yellow 11 (Cl... 

Bis(2,4,6-trinitrophenyl)methane when treated with NaAc in acetic acid produced (580) as a thermostable explosive (80MIP41600). The conversion of o-nitrotoluene into 2,1-benzisoxazole was effected by mercury(II) oxide catalysis. A mercury containing intermediate was isolated and was demonstrated to be converted into 2,1-benzisoxazole (67AHC(8)277). The treatment of o-nitrotoluene derivative (581) with sulfuric acid gave (582) in 35% yield (72MI41607). 

Preparation of the prototype in this series, procaine (31). i.irts with the oxidation of p-nitrotoluene (27) to the corre-Hiding benzoic acid (28). This is then converted to the acid ll Inride (29) reaction of the halide with diethyl aminoethanol fiI lords the so-called basic ester (30). Reduction by any of a .fl ics of standard methods (e.g., iron and mineral acid, cata-Ivlic reduction) affords procaine (31). ... 

Oxidative coupling of o-nitrotoluene gives 4,4 -dinitrodibenzyl which is reduced with hydrogen to the diamine. The diamine is pyrolyzed to give dihydrobenzazepine. This is reacted with N-(3-chloropropvl)-N-methylbenzamine to give N-benzyldesipramine. This is debenzylated by reductive cleavage and then reacted with HCI. 

Toluene (methylbenzene) is similar to benzene as a mononuclear aromatic, but it is more active due to presence of tbe electron-donating metbyl group. However, toluene is much less useful than benzene because it produces more polysubstituted products. Most of tbe toluene extracted for cbemical use is converted to benzene via dealkylation or disproportionation. Tbe rest is used to produce a limited number of petro-cbemicals. Tbe main reactions related to tbe cbemical use of toluene (other than conversion to benzene) are the oxidation of the methyl substituent and the hydrogenation of the phenyl group. Electrophilic substitution is limited to the nitration of toluene for producing mono-nitrotoluene and dinitrotoluenes. These compounds are important synthetic intermediates. 

Nitrobenzaldehyde has been prepared from />-nitrotoluene by treatment with isoamyl nitrite in the presence of sodium methylate,1 by oxidation with chromyl chloride,2 cerium dioxide,3 or chromium trioxide in the presence of acetic anhydride.4 It can also be prepared by the oxidation of -nitrobenzyl chloride,5 7>-nitrobenzyl alcohol,6 or the esters of -nitrocinnamic acid.7... 

The effect of solvent upon k2 has been reported , and it was concluded that the activated complex is not sufficiently polar to be called ionic . The oxidations of toluene and triphenylmethane exhibit primary kinetic deuterium isotope effects of 2.4 and ca. 4 respectively. No isotopic mixing occurred during formation of the Etard complex from a mixture of normal and deuterated o-nitrotoluene . The chromyl chloride oxidation of a series of substituted diphenylmethanes revealed that electron-withdrawing substituents slow reaction while electronreleasing groups have the opposite effect, the values ofp andp being —2.28 + 0.08 and —2.20 + 0.07 respectively . ... 

An D, DT Gibson, JC Spain (1994) Oxidative release of nitrite from 2-nitrotoluene by a three component enzyme system from Pseudomonas sp strain JS42. J Bacterial 176 7462-7467. 

Robertson JB, JC Spain, JD Haddock, DT Gibson (1992) Oxidation of nitrotoluenes by toluene dioxygenase evidence for a monooxygenase reaction. Appl Environ Microbiol 58 2643-2648. 

The degradation of 4-nitrotoluene by Pseudomonas sp. takes place by oxidation to 4-nitrobenzoate via 4-nitrobenzyl alcohol and 4-nitrobenzaldehyde (Haigler and Spain 1993 Rhys-Williams et al. 1993 James and Williams 1998). 

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