O-Nitro toluene

AI3-16311 Benzene, 1-methyl-2-nitro- CCRIS 1224 EINECS 201-853-3 HSDB 2189 o-MethyInitrobenzene Nitrotoluene, 0- 0-Nitfotoluene ortho-Nitrotoluol NSC 9577 ONT Toluene, o-nitro- UN1664. Liquid mpn-10° bp = 222° d = 1.1611 Xm = 254 nm (e= 4330, MeOH) insoluble in H2O, very soluble in EtOH, Et20, less soluble in CCI4. 

Three products are possible from nitration of toluene o mtrotoluene m nitro toluene and p mtrotoluene All are formed but not m equal amounts Together the ortho and para substituted isomers make up 97% of the product mixture the meta only 3%... 

Chlorpromazine and other phenothiazines can be identified by their reactions with benzene-, toluene-o-, and toluene /j-stilbinic acids, and with p-hydroxy-, m-nitro-, w-amino-, and p-nitrobenzene stilbinic acids in an HCl medium. The reaction products are initially colorless masses but rapidly oxidize to yield colored products [32]. 

A. o-Nitrobenzylpyridinium bromide. A 1-1. flask fitted with a reflux condenser is charged with 102 g. (0.744 mole) of o-nitro-toluene, 120 g. (0.675 mole) of N-bromosuccinimide, 1.0 g. of benzoyl peroxide, and 450 ml. of dry carbon tetrachloride. The mixture is heated under reflux until, after the refluxing is temporarily interrupted, all the solid is seen to float on the surface (usually 6-8 hours suffices). 

Very pure material can be obtained by dissolving o-nitro-benzaldehyde in toluene and precipitating with petroleum ether, according to earlier instructions.3... 

A mixture of 30.2 g. (0.20 mole) of o-nitrobenzaldehyde,2 40 g. (0.29 mole) of phenylacetic acid, 100 ml. (1.08 moles) of acetic anhydride, and 20 g. (0.20 mole) of triethylamine is refluxed for 15 minutes in a 500-ml. flask. The solution is cooled to 90°, and 100 ml. of cold water is added over a 5-minute period at a rate that maintains the temperature above 90° (Note 1). The solution is filtered at 95-100° and cooled to 20°. frims-o-Nitro-a-phenylcinnamic acid precipitates in the form of light-orange crystals. It is separated by filtration and washed with 60 ml. of 50% acetic acid and with water. The dried acid weighs 39-42 g. (72-77%) and melts at 195-198°, which corresponds to a purity of about 98% (Note 2). After recrystallization from 500 ml. of toluene, it is in the form of yellow prisms weighing 38-39 g. (71-72%) and melting at 197.8-198.3°. 

Recently Kobe, Skinner and Prindle [32] reported their extensive studies on the nitration of o- and p- nitrotoluenes to dinitrotoluene. They concluded that the most favourable parameters of the nitration of o- and p- nitrotoluenes differed somewhat from each other. Thus the concentration of mixtures for nitrating o- nitro-toluene might vary within a wider range, especially with regard to the quantity of sulphuric acid. Also, lower temperatures may be applied for the nitration of o- nitrotoluene. 

A similar EGB-induced reaction may take place during the reduction of o-nitro-toluene in DMF in the presence of paraformaldehyde to 2-(2-nitrophenyl)ethanol and 2-(2-nitrophenyl)propane-1,3-diol [129]. 

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