N- />-toluidine

The checkers prepared N-o-tolylformamide3 as follows. A solution of 100 g. (0.94 mole) of n-toluidine and 82 ml. (100 g., 2.13 moles) of 98% formic acid in 300 ml. of toluene is refluxed under a condenser attached to a water separator.4 After water... 

Ninety grams (90.2 ml., 0.839 mole) of n-toluidine is slowly added to a mixture of 90 ml. of glacial acetic acid and 180 ml. (1.90 mole) of acetic anhydride contained in a 750-ml. twonecked flask equipped with a thermometer and a two-hole cork stopper for a gas inlet tube (Note 1). Acetylation occurs with evolution of heat. The mixture is cooled in an ice bath (Note 2) and nitrosated by rapid admission of a stream of nitrous gases (Note 3). The nitrous gases are obtained by the action of nitric... 

Although the yields of substituted pyridines from the toluidines is low, they suffice to show that in this example also they are formed exclusively by an exchange of the N and ortho C atoms. For instance, the only substituted pyridines formed from /n-toluidine are 2,4- and 2,6-lutidine, plus 2,4,6-collidine as a result of subsequent transmethylation. The main pyridine-type product formed from o-tolui-dine, 2,3-lutidine, is a result of N/ortho-C exchange also (Scheme 3). Thus, all three toluidines lead to lutidines and 2,4,6-collidine by the exclusive interchange of the N and ortho C atoms in combination with isomerization of the toluidines. 

Not only simple iV-alkyl-iV-nitr osoanilines 303,308 undergo this reaction, but also ring-substituted aniline derivatives with a free />ara-position, such as iV-ethyl-jV-nitroso-n-toluidine,303 m-chloro- and m-bromo-iV-methyl-jV-nitro-soaniline,310 and iV-methyl-JV-nitrosoanthranilic acid 301,311 the C-nitroso derivative obtained from the last-mentioned compound can be hydrolysed to nitrosalicylic acid.312 Rearrangements of the derivatives of 1- and 2-naph-thylamine have been reported by several authors.305,308,309,313... 

Fujita et al. [68] have also reported that o- and m-toluidines give the same polymer upon electropolymerization. The cyclic voltammograms of PMT were obtained in HCl and in Na2S04 solution. Oxidation and reduction of polytoluidine in HCl take place in two steps, while they proceed in one step in Na2S04. Cattarin et al. [65] have reported a two-step reversible oxidation for poly (o- and w-toluidines) like PANI from cyclic voltanunetric studies and that o- and /n-toluidines give the same polymer. 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Reaction takes place on nitrogen when the electrophilic center is an sp carbon, particularly if it is charged. Thus Mannich reaction yields the N-substituted compound (71 and 72) (Scheme 34) (54. 157-159). The same reaction is reported with piperidine, o-toluidine. and methylaniline (158). 

Acryhc stmctural adhesives have been modified by elastomers in order to obtain a phase-separated, toughened system. A significant contribution in this technology has been made in which acryhc adhesives were modified by the addition of chlorosulfonated polyethylene to obtain a phase-separated stmctural adhesive (11). Such adhesives also contain methyl methacrylate, glacial methacrylic acid, and cross-linkers such as ethylene glycol dimethacrylate [97-90-5]. The polymerization initiation system, which includes cumene hydroperoxide, N,1S7-dimethyl- -toluidine, and saccharin, can be apphed to the adherend surface as a primer, or it can be formulated as the second part of a two-part adhesive. Modification of cyanoacrylates using elastomers has also been attempted copolymers of acrylonitrile, butadiene, and styrene ethylene copolymers with methylacrylate or copolymers of methacrylates with butadiene and styrene have been used. However, because of the extreme reactivity of the monomer, modification of cyanoacrylate adhesives is very difficult and material purity is essential in order to be able to modify the cyanoacrylate without causing premature reaction. 

BenZotrichloride Method. The central carbon atom of the dye is supphed by the trichloromethyl group from iJ-chlorobenzotrichloride. Both symmetrical and unsymmetrical triphenyhnethane dyes suitable for acryhc fibers are prepared by this method. 4-Chlorobenzotrichloride is condensed with excess chlorobenzene in the presence of a Lewis acid such as aluminium chloride to produce the intermediate aluminium chloride complex of 4,4, 4"-trichlorotriphenylmethyl chloride (18). Stepwise nucleophihc substitution of the chlorine atoms of this intermediate is achieved by successive reactions with different arylamines to give both symmetrical (51) and unsymmetrical dyes (52), eg, N-(2-chlorophenyl)-4-[(4-chlorophenyl) [4-[(3-methylphenyl)imino]-2,5-cyclohexadien-l-yhdene]methyl]benzenaminemonohydrochloride [85356-86-1J (19) from. w-toluidine and o-chloroaniline. 

Synthesis. Methods of synthesis have changed Htde since the synthesis of Basic Red 2. One method starts with o-toluidine [95-53-4] C H N, which is diazotized and coupled to form amino azotoluene [97-56-3] Amino azotoluene is reduced to one mole each of o-toluidine and... 

Monoazo Pigments. In combination with other groups, the a2o linkage, —N=N—, imparts color to many dyes and pigments (see Azo Dyes). The simplest of these, ie, the Hansa yellows, toluidine reds, and naphthol reds, do not have the lightfastness and heat stabiUty required for plastics. Permanent YeUow FGL and Permanent Red 2B are stable enough for vinyls, polyethylene, polypropylene, and ceUulosics (11). Permanent Red 2B is available as the calcium, barium, or manganese salt. 

Dimethyl-4-heptanone (diisobutyl ketone) Dimethyl sulphate N,N-Dimethyl-p-toluidine Dimethylamine... 

Chemical Designations - Synonyms-. 2,6-Dinitro-N,N-dipropyl-4-trifluoromethylaniline 2,6-Dinitro-N,N-dipropyl-alpha, alpha-trifluoro-p-toluidine N,N-Dipropyl-2,6-dinitro-4-trifluoro-methylamline Treflan alpha, alpha-Trifluoro-2,6-diiiitro-N,N-dipropyl-p-toluidine Chendad Formula-. Ci3H, 3N304 Observable Characteristics - Physical State (as normally shipped)-. Solid Color. Yellow-orange Odor. Data not available. 

The foinialion of iosaniiine fioni a mi tuie of aniline, o- and / -toluidine is represented by assiiining that the methyl-gioup of /-toluidine acts as the link which connects the nuclei of aniline and n-toiuidine. 

The acylation of dienamines has not been extensively investigated. The dienamine (127) prepared by Birch reduction of N,N-dimethyl-p-toluidine has been shown to react with diketene (90) to give the chromone (128), showing that attack occurs at the /9-carbon of the dienamine system. 

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