Chloro-4-aminotoluene

A solution of 60 g (0.57 mole) of sodium chlorate in 70 ml. of water is added slowly with stirring at 5° to a solution of 200 g. (1.35 moles) of acetyl-p-toluidine in 400 ml. of acetic acid and 600 ml. of concentrated hydrochloric acid. The mixture is stirred for 30 minutes, 400 ml. of additional concentrated hydrochloric acid is added, and the mixture is refluxed 2 hours and steam-distilled to remove the acetic acid and some oily material. The residual solution is then made alkaline and steam-distilled to remove the amine. The amine is extracted from the distillate with ether, and the ethereal solution is distilled to give 225 g. (60%) of 3-chloro-4-aminotoluene boiling at 220-225°. The product contains small amounts of p-toluidine and dichloro-p-toluidine. 

Sixty grams (0.52 mole) of chlorosulfonic acid is cooled to —15° and agitated while 20 g. (0.18 mole) of chlorobenzene is added drop-wise over a period of 2 hours. The temperature is held in the range — 5° to —10° during this operation and for an additional 2 hours. After standing at room temperature for 12 hours, the mixture is 

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Other common intermediates for azo pigment production are 2,4-dinitro-aniline, acetoacet-o-chloroanilide, acetoacet-o-toluidide, phenyl- and p-tolyl-methylpyrazolone, 2-hydroxy-3-naphthoic acid, Naphtol AS and its derivatives, and 2-chloro-4-aminotoluene-5-sulfonic acid. 

Synonyms 2-Amino-5-chlorotoluene 3-chloro-6-aminotoluene 5-chloro-2-amino-toluene 4-chloro-2-methylaniline 4-chloro-6-methylaniline 4-chloro-2-toluidine / ara-chloro-ort/ro-toluidine 2-methyl-4-chloroaniline 2-methyl-4-chlorobenzene-amine... 

Synonyms 2-Amino-4-chlorotoluene 4-chloro-2-aminotoluene 3-chloro-6-methyl-aniline 5-chloro-2-methylaniline 5-chloro-2-toluidine 2-methyl-5-chloroaniline... 

Chlorine Trifluoride Chlordacetic Acid Chloroacetic Acid, Ethyl Ester Chloroacetophenone Alpha-chloroacetophenone Omega-chloroacetophenone Chloroacetyl Chloride 5-Chloro-2-Aminotoluene... 

The most important diazo components are 4-nitroaniline [100-01-6], 2-chloro-4-nitroaniline [121-87-9], 2-cyano-4-nitroaniline [17420-30-3], 2,4-dinitroaniline [97-02-9], 2,6-dichloro-4-nitroaniline [99-30-9], 2-bromo- [1817-73-8] and 2-chloro-4,6-dinitroaniline [3531-19-9], and 2-bromo-6-cyano-4-nitroaniline [17601-94-4], The coupling components are derived from aniline, 3-aminotoluene 1108-44-1], 3-chloroaniline [108-42-9], 3-aminoacetanilide [102-28-3], and 3-amino-4-alkoxyacetanilide by /V-alkylation. 

AMINO-2-CHLOROTOLUENE 2-CHLORO-4-AMINOTOLUENE 3-CHLORO-4-METHYLANILINE CPT DKC 1347 DRC 1339 NCI-C02040... 

SYNS AMARTHOL FAST RED TR BASE 2-AMINO-5-CHLOROTOLUENE AZOENE FAST RED TR BASE AZOGENE FAST RED TR AZOIC DIAZO COMPONENT 11 BASE BRENTAMINE FAST RED TR BASE 5-CHLORO-2-AMINOTOLUENE 4-CHLORO-2-METHYLANILINE 4-CHLORO-6-METHYLANILINE 4-CHLORO-2-iMETHYLBENZENEAMINE 4-CHLORO-2-TOLUIDINE DAITO RED BASE TR DEVAL RED K DEVAL RED TR DIAZO FAST RED TRA FAST RED BASE TR FAST RED 5CT BASE FAST RED TR FAST RED TRll FAST RED TR BASE FAST RED TRO BASE KAKO RED TR BASE KAMBA. nNE RED TR 2-METHYL-4-CHLOROANILINE MITSUI RED TR BASE RED BASE CIBA IX RED BASE IRGAIX RED BASE NTR RED TR BASE SANYO FAST RED TR BASE TULABASE FAST RED TR... 

CHLORO-2-AMINOTOLUENE 3-CHLORO-6-METHYLANILINE 5-CHLORO-2-METHYLANILINE FAST RED KB AMINE FAST RED KB BASE FAST RED KB SALT FAST RED KB SALT SUPRA FAST RED KBS SALT GENAZO RED KB SOLN HILTONIL FAST RED KB BASE LAKE RED KB BASE METROGEN RED FORMER KB SOLN NAPHTHOSOL FAST RED KB BASE NCI-C02051 PHARMAZOID RED KB RED KB BASE SPECTROLENE RED KB STABLE RED KB BASE... 

SYNS 2-AMINO-3-CHLOROTOLUENE 3-CHLORO-2-AMINOTOLUENE 6-CHLORO-2-METHYLANILINE... 

Lake Red carbon. Red pigments made by coupling 2-chloro-5-aminotoluene-4-sulfonic acid with (3-naphthol and forming various metal salts. 

CHLORO-2-AMINOTOLUENE or 5-CHLORO-2-AMINOTOLUENE (95-794) CtHjCIN Combustible solid (flash point unknown Fire Rating 1). Dust or powder forms explosive mixture with air. Violent... 

B acid 3-14-00-02216 Beilstein Handbook Reference) 4-Amino-2-chlorotoluene-5-sullbnic acid 4-Amino-6-chlorotoluene-3-sulphonic acid 2-Amino-4-chioro-5-methylbenzenesulfonic acid 6-Amino-4-chloro-m-toluenesuifonic acid Benzenesuifonic acid, 2-amino-4-chioro-5-methyi- Briiliant Toning Red Amine BRN 2727161 CCRIS 3406 2-Chloro-4-aminotoluene-5-sulfonic acid 4-Chioro-6-amino-m-toiuenesulfbnic acid 3-Chioro-4-methyianiline-6-suifonic acid 2-Chloro-4-toluidine-5-sulfonic acid EiNECS 201-837-6 HSDB 5258 Kyseiina 2-chlor-4-toiuidin-5-suifonova Permanent Red 2B Amine Red 2B acid m-Toiuenesuifonic acid, 6-amino-4-chloro-. 

Chloro-3-amino-1,4-naphthoquinone. See 2-Amino-3-chloro-1,4-naphthoquinone 2-Chloro-4-aminotoluene. See 3-Chloro-p-toluidine... 

Chloro-2-aminotoluene hydrochloride. See4-Chloro-o-toluidine hydrochloride... 

Synonyms 1-Amino-3-chloro-4-methylbenzene 4-Amino-2-chlorotoluene Benzenamine, 3-chloro-4-methyl- 2-Chloro-4-aminotoluene 3-Chloro-4-methylaniline 3-Chloro-4-methylbenzenamine 2-Chloro-p-toluidine CPT 3-CPT Starlicide p-Toluidine, 3-chloro-Empirical C7H8CIN Formula CH3C6H3(CI)NH2 Properties Clear to tan oily liq. or brn. solid mild odor sol. in DMSO, 95% ethanol, acetone sol. < 1... 

Synonyms 1 -Amino-3-chloro-6-methylbenzene 2-Amino-4-chlorotoluene 4-Chloro-2-aminotoluene 3-Chloro-6-methylaniline 5-Chloro-2-methylaniline 5-Chloro-2-methylbenzenamine Fast red KB amine Fast red KB base Fast red KB salt Red KB base... 

Synonyms 2-Amino-5-chlorotoluene hydrochloride Azoic diazo component 11 base 5-Chloro-2-aminotoluene hydrochloride 4-Chloro-2-methylaniline hydrochloride 4-Chloro-6-methylaniline hydrochloride 4-Chloro-2-methylbenzenamine hydrochloride 4-Chloro-2-toluidine hydrochloride p-Chloro-o-toluidine hydrochloride Cl 37085 Cl azoic diazo component 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.

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