4-Chloro-2-toluidine

Naphthylamine, 4-aminodiphenyl, 4-chloro-2-toluidine, benzidine, 2,4,5-trimethylaniline, 2,4-diaminoanisol, 2,4-toluylenediamine, 2-amino-4-nitrobenzene, 3,3 -dichlorobenzidine, 3,3 -dimethoxybenzidine, 3,3 -dimethylbenzidine, 3,3 -4,4 -diaminodiphenylmethane, 4,4 -diaminodiphenybnethane, 4,4 -methylene-bis-(2-chloroaniline), 4,4 -Oxydianiline, 4,4 -thiodianiline, 2-aminoazotoluene,... 

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... 

Chloronitrotoluene and 2,6-chlorotoluidine are technically important in other respects also. The former compound is the starting material for the prepara-oitn of 4,4 -dichloroindigo, which yields, on further chlorination or bromination, the very greenish 4,5,4, 5 -tetrahalogenindigos (e.g., brilliant indigo 4G). 2,6-Chloro-toluidine, as fast scarlet TR base, is used in generating ice colors (naphthol AS). The isomeric 4-chloro-2-toluidine (fast red KB base), prepared by reduction of the by-product 4-chloro-2-nitrotoluene, is used for the same purpose. 

Chloro-2-toluidine, 164 6-Chloro-2-toluidine, 161, 164 Chrome brown R, 115 Chrcmic add, 8 Chrcnnium sulfate, 4... 

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... 

Azoic diazo component 11 (4-chloro-2-toluidine hydrochloride, 2-methyl-4-chloro-aniline hydrochloride, 5-chloro-2-amino toluene hydrochloride 4-chloro-2-methyl benzeneamine hydrochloride, azanil red salt TRD, fast red salt TRA, Cl 37085) [316593-3]... 

Chloro-2-toluidine hydrochloride. See4-Chloro-o-toluidine hydrochloride 4-Chloro-o-toluidine hydrochloride CAS 3165-93-3... 

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... 

DOT CLASSIFICATION 6.1 Label KEEP AWAY FROM FOOD SAFETY PROFILE Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also other chloro toluidine entries. 

After development on TLC plates, amino-substituted 1,3,5-triazines can be revealed by use of the chloro-toluidine reaction <83JC97>. This is a sensitive method developed for the detection of amino and imino compounds on paper chromatograms. The method depends on the formation of chloramines which are then detected by liberation of iodine from a starch-potassium iodide reagent. 

Important analogs of aniline include the toluidines, xyUdines, anisidines, phenetidines, and its chloro-, nitro-. A/-acetyl. A/-alkyl. A/-aryl. A/-acyl, and sulfonic acid derivatives. 

The reactivities of compounds of type 6 with aniline in acetone correlate quite well with substituent effects, and autocatalysis is unimportant here. In the less polar tetrahydrofuran, where the hydrochloride is only partly soluble, the reaction shows autocatalysis when aniline and -chloro aniline are reactants but not when the more basic -toluidine is involved. In these cases the solubility of the acidic product may also influence the differential behavior observed. 

Preparation of Intermediate Compound 2-Methyl-3-o-Tolyl-6-Sulfamyl-7-Chloro-4(3H)-Quinazoiinone Set up a 5-liter 3-necked flask fitted with a stirrer, condenser and a drying tube. To a stirred mixture of 100 g (0.342 mol) of powdered 4-chloro-5-sulfamyl-N-acetylanthranilic acid, 40.2 g (0.376 mol) of o-toluidine and 2.0 liters of dry toluene was added dropwise, over a period of 15 minutes, 21.7 ml (34.1 g) (0.248 mol) of phosphorus trichloride. The mixture was then refluxed for 10 hours. The solid turned somewhat gummy towards the latter part of the first hour. The mixture then became more free flowing as heating was continued. Let stand overnight. The yellow solid was filtered, washed with toluene and dried. The toluene filtrate was discarded. The dried solid was triturated with 1.5 liters of 10% sodium bicarbonate, filtered and the cake washed with water. The filtrate on acidification yielded 11.5 g of the starting acid. The damp product was dissolved in 4,5 liters of 95% ethanol and the solution treated with charcoal and filtered. On cooling filtrate yielded 69.5 g (55.5%) of the title compound, MP 271.5° to 274°C. 

First there is chlorination of nitrogen to yield reactive N-chloro derivatives, which oxidize iodide to iodine in the next step. Finally oxidation of the o-toluidine probably yields colored quinonoid toluidine derivatives. 

Information about the products of a reaction can be particularly informative when one of them is quite unexpected. Thus the reaction of chloro-4-methylbenzene (p-chlorotoluene, 6) with amide ion, eNH2, in liquid ammonia (p. 173) is found to lead not only to the expected 4-methylphenylamine (p-toluidine, 7), but also to the quite unexpected 3-methylphenylamine (w-toluidine, 8), which is in fact the major product ... 

Chlorotriethylamine, d328 2-Chloro-2-(trifluoromethyl)aniline, al41 Chloro-a,a,a-trifhiorotoluenes, c60, c61, c62 4 -Chloro- a,a, a-trifhioro-o-toluidine, a 142... 

Fig. 3.61. HPLC-UV chromatogram at 230 nm for the analysis of the aromatic amines listed. (1) 1,4-Diaminobenzene (2) 2-chloro-l,4-diaminobenzene (3) 2,4-diaminotoluene (4) benzidine (5) 4,4 -oxidianiline (6) aniline and 4-nitroaniline (7) o-toluidine (8) 4,4 -methylenedianiline (9) 3,3 -dimethoxibenzidine (10) 3,3 -dimethylbenzidine (11) 4-chloroaniline and 2-amino-4-nitrotoluene (12) 4,4 -thiodianiline (13) p-cresidine (14) 2,4-dimethylaniline (15) 2-naphty-lamine (16) 4-chloro-o-toluidine (17) 4,4 -methylene-di-o-toluidine (18) 2,4,5-trimethylaniline (19) 4-aminobiphenyl (20) 3,3 -dichlorobenzidine (21) 4,4 -methylenbis (2-chloroaniline) and (22) o-aminoazotoluene. Reprinted with permission from M. C. Garrigos et al. [130].

The products produced by interaction of diazonium salts and iodides are unstable and liable to be explosive in the solid state. They are usually the triiodides, but monoiodides have been isolated under specific conditions from diazotised aniline and o-toluidine. Products prepared from diazotised o-, m- or p-nitroanilmes, m-chloro-, -methoxy-, or -methyl-aniline are too unstable to isolate, decomposing below 0°C. 

List of Abbreviations BCIP, 5-bromo-4-chloro-3-indolyl phosphate, toluidine salt CCD, charged-coupled device CNS, central nervous system cDNA, copy or complimentary RNA cRNA, copy or complimentary RNA DNase, deoxyribonuclease FITC, fluorescein isothiocyanate mRNA, messenger RNA NBT, nitro blue tetrazolium choride PCR, polymerase chain reaction RNase, ribonclease... 

Chlorotoluene, see Toluene 4 -Chloro-o-toluidine, see Chlornhenamldlne. Chlordimeform... 

Carbon tetrachloride. Chloroform, 2-Chlorophenol, Cyclohexanol, Cyclopentene, 1,1-Dichloroethylene, irans-l, 2-Dichloroethylene, IV.yV-Dimethylaniline, lV,lV-Dimethylformamide, 2,4-Dimethylphenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Ethyl formate. Formaldehyde, Glycine, Methanol, Methylene chloride. Methyl formate, 2-Methvlphenol. Monuron, 4-Nitrophenol, Oxalic acid, Parathion, Pentachlorophenol, Phenol, l idine. Styrene, Trichloroethylene, Vinyl chloride Formylacetic acid, see cis-l,3-Dichloropropylene, irans-1,3-Dichloropropylene IV-Formylcarbamate of 1-naphthol, see Carbaryl Formyl chloride, see Chloroethane, Chloroform, sym-Dichloromethyl ether, ds-1,3-Dichloropropylene, irans-ES-Dichloropropylene, Methyl chloride. Methylene chloride. Trichloroethylene, Vinyl chloride lV-Formyl-4-chloro-o-toluidine, see Chlornhenamidine. 

CASRN 6164-98-3 molecular formula C10H13CIN2 FW 196.68 Plant Principal soil and/or plant metabolites included p-chloro-o-toluidine, A -(4-chloro-o-tolyl)-A-methylformamidine, and A/-formyl-p-chloro-o-toluidine (Verschueren, 1983). p-Chloro-o-toluidine, A/ -(4-chloro-o-tolyl)-A/-methylformamidine, and TV-formyl-p-chloro-o-toluidine were identified in rice grains and straws at concentrations of 3-61, 0.2-1, 10-38 and 80-6,900, 10-180, 67-500 ppb, respectively (lizuka and Masuda, 1979). 

Chemical/Physical. The following compounds were identified as metabolites in rice plants after treatment with chlorphenamidine 7V-(4-chloro-o-tolyl)-7V-methyl formamidine, 7V-formyl-4-chloro-o toluidine, and 4-chloro-o toluidine (Lizuka and Masuda, 1979). 

Those degradation products which have been identified in our investigations are 1-naphthol from carbaryl, 2,4-D acid and 2,4-dichlorophenol from 2,4-D ester, 2-chloro-2, 6 -diethylacetanilide from alachlor, o,o,oe-trifluro-2-nitro-6-amino-N,N-dipropyl-p-tolu-idine and o,o,o-trifluro-2,6-diamino-N,N-dipropyl-p-toluidine from trifluralin, and a variety of phenols and acids from the degradation of the aromatic solvents used in the formulation of the liquid pesticides as emulsifiable concentrates (41,42). 

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