2-Nitro-6-chlorotoluene

Uses. (9-Nitrotoluene is used in the synthesis of intermediates for azo dyes, sulfur dyes, mbber chemicals, and agriculture chemicals. Typical intermediates are o-toluidine, o-nitrobenzaldehyde, 2-nitro-4-chlorotoluene, 2-nitro-6-chlorotoluene, 2-amino-4-chlorotoluene (Fast Scarlet TR Base), and 2-amino-6-chlorotoluene (Fast Red KB Base). -Nitrotoluene is used principally in the production of intermediates for azo and sulfur dyes. Typical intermediates are -toluidine, -nitrobenzaldehyde, and 4-nitro-2-chlorotoluene. 

A solution of 100 g. (0.58 mole) of 2-nitro-4-chlorotoluene in 500 ml. of pyridine and 390 ml. of water is heated on a steam bath under a reflux condenser while 6 portions of 43 g. each of potassium permanganate are added at intervals of 1 hour. After another 1-hour heating period, the mixture is filtered and the water and pyridine are removed from the filtrate by evaporation under reduced pressure. The residue is treated with excess aqueous sodium hydroxide solution, any oil present is removed by use of a separatory funnel, and the resulting aqueous solution is acidified with hydrochloric acid. The precipitated 2-nitro-4-chlorohenzoic acid is collected hy filtration, washed with water, and dried to give 56A g. (48%) of product melting at 138-140°. 

A useful application in the manufacture of ion-exchange resins may well be possible which avoids the use of carcinogenic chloromethyl ether. Here, a polymer of p-methyl styrene is chlorinated on the side chain with aqueous NaOCl and a phase-transfer catalyst. Sasson et al. (1986) have shown how stubborn . substituted aromatics like nitro/chlorotoluenes can be oxidized to the corresponding acids by using aqueous NaOCl containing Ru based catalyst. 

The ring-chlorinated derivatives of toluene form a group of stable, industrially important compounds. Many chlorotoluene isomers can be prepared by direct chlorination. Other chlorotoluenes are prepared by indirect routes involving the replacement of amino, hydroxyl, chlorosulfonyl, and nitro groups by chlorine and the use of substituents, such as nitro, amino, and sulfonic acid, to orient substitution followed by their removal from the ring. 

Nitro- 2-, 4, 5 6- chlorotoluenes (Ref 2) and 4-Nitro- 2- 3- chlorotoluenes(Ref 3). All are low melting cryst solids, except 3-Nitro-4-chloro 4-Nitro-3-chlorotoluenes which are definitely liquids at RT... 

The nitration of chlorobenzene, dichlorobenzene, and chlorotoluene leads to substances of considerable value in dye chemistry in that nitro groups in position 2- and 4- relative to chlorine having an activating effect [11]. 

Toluene-4-sulfonic acid is used as a starting material in the production of 2-chloro-5-aminotoluene-4-sulfonic add (CLT-acid). CLT-acid is manufactured by chlorination of toluene-4-sulfonic add, transformation of 2-chlorotoluene-4-sulfonic add into 2-chloro-5-nitrotoluene-4-sulfonic acid followed by the reduction of the nitro group with iron/HCl. CLT-acid is used, for example, as a raw material in the production of Pigment Red 52 1, Pigment Red 53 1 and other metal complexes. 

Figure 10.3. Aryl derivatives (clockwise from the top) 4-chloro-l-methylbenzene (4-chlorotoluene), methylbenzene (toluene), 4-cyano-l-methylbenzene (4-cyanotoluene), 4-fluoro-l-methylbenzene (4-fluorotoluene), 4-nitro-l-methylbenzene (4-nitrotoluene) prepared by copper(I) salt-catalyzed decomposition of the diazonium salt generated on treatment of 4-amino-l-methylbenzene, (4-aminotoluene) with sodinm nitrite (NaN02), and protic acid.

Chloro Nitro Ethane Chlorosulfonic Acid Chlorotoluene Chlorotrifluoroethylene Chlorox... 

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