Aniline, 2,4,5-Trimethyl

Aminomesitylene 2-Aminomesitylene 1-Amino-2,4,6-trimethylbenzen 2-Amino-1,3,5-trimethylbenzene Aniline, 2,4,6-trimethyl- Benzenamine, 2,4,6-trimethyl- CCRIS 2871 EINECS 201-794-3 HSDB 2694 Mesidin Mesidine Mesitylamine Mesitylene, 2-amino- 2,4,6-Trimethylaniline 2,4,6-Trimethylbenzenamine. Used as an intermediate in the manufacture of dyestuffs, mp = -2.5° bp = 232.5° d = 0.96330 = 234, 28... 

TRIHETHYL ANILINE TRIMETHYL BENZENE 1,2,4-TRIHETHTL BENZENE... 

Mesitylene is converted to a dye iatermediate, 2,4,6-trimethyl aniline [88-05-1] (mesidine), via nitration to l,3,5-trimethyl-2-nittobenzene [603-71-4] followed by reduction, eg, catalytic hydrogenation (38). Trinitromesitylene has been prepared for use ia high temperature tolerant explosives (39). The use of mesitylene to scavenge contaminant NO from an effluent gas stream has been patented (40). 

The aniline derivative 332, prepared from 2-fluoro-6-nitrotoluene, was transformed through successive reactions as shown in Scheme 60 to give the functionalized indole 333. It was then reduced with LiAlH4 to the dimethylaminopropyl derivative which was quaternized with Mel to the trimethyl ammonium salt 334. Subsequent cyclization and functionalization afforded the pyrroloquinoline 335. The latter could be transformed to the tetracyclic acid 336 (90JHC2151). (Scheme 60)... 

Bromo-Ar,Ar-dimethyl-3-(trifluoromethyl)aniline has been prepared by the methylation of 4-bromo-3-(trifhioromethvl)aniline with trimethyl phosphate in 70-80% yield.3 The present method, which effectively uses 3-(trifluoroinethyl)aniline as starting material, offers advantages in cost, yield, and ease of purification. 

N-Nitroso compounds occur in many operations in the rubber industry. Some nitrosamines (nitrosodiphenylamine, N-N-dinitrosopentamethylenetetramine, polymerized N-nitroso 2,2,4-trimethyl-l,2-dihydroquinoline and N-methyl-N-4-dinitroso aniline) are used as organic accelerators and antioxidants in the production of rubber and often the products are found to be contaminated with such compounds [19]. 

An iridium(I) complex with the l,2-bis(tcrt-butylmethylphosphino)ethane (4) and tetrakis(3,5-bis(trifluoromethyl)phenyl)borate as the counter anion catalyzes the hydrogenation of several acyclic aromatic Ai-arylimines under atmospheric hydrogen pressure at room temperature, giving the desired chiral amines with high-to-excellent enantioselectivities (up to 99%, Fig. 6) [19]. The authors also tested (S )-BINAP (Fig. 1) and (/ )-Ph-PHOX (PHOX = 2-[2-(diphenylphosphino) phenyl]-4,5-dihydrooxazole) hgands with lower enantioselectivities [19]. Both steric and electronic properties of the ligand and the combination with the BArF anion are in the base of the efficacy of this catalytic system. On the other hand, attempted hydrogenations of Ai-(2,2,2-trifluoro-l-phenylethylidene)aniline and M-(l,2,2-trimethyl-propylidene)aniline under the same conditions resulted in... 

The bipolar 4,5-diethyl-2,2,3-trimethyl-l-(2-trifluoromethylphenyl-l,2,5-azastannaborole) (322) (obtained from 1,1,4,5,5-pentaethyl-2,2,3-trimethyl-l,2,5-azastannaborole and 2-trifluromethyl-aniline) undergoes a thermal elimination of ethane (100°C, toluene) giving a derivative of 2,5-dihydro-17f-1,2,5-azastannaborole (323) (Scheme 31) <87ZN(B)l9l>. 

Mit N,N-Dimethyl- und N,N,4-Trimethyl-anilin erhalt man die folgenden Verbindungen233 ... 

Die Oxidation von 2,4,5-Trimethyl-anilin mit Dihydrogenperoxid/Meerrettich-Peroxidase liefert 2,2, 4,4, 5,5 -Hexamethyl-azobenzol zu 25% neben einem Benzochinon5. Eine ahn-liche Oxidation findet auch statt, wenn Aniline, die in Kontaktherbiziden Verwendung finden (z.B. Propansaure-3,4-dichlor-anilid) in die Erde gelangen. Propansaure-3,4-di-chlor-anilid wird zunachst mikrobiologisch zu 3,4-Dichlor-anilin reduziert und anschlie-Bend durch Peroxidase-Reaktion in 3,3, 4,4 -Tetrachlor-azobenzol iibergefuhrt6. 

NOz H3C rCH3 LiAlH4/Elher RiickfluB 6 h 2,4,6-TrimethyI-anilin (+Bis-[2,4,6-trimethyl-pheny[ -diazen) 61 [+11] 5... 

Auch die Reaktion von Azido-benzol und seinen Methyl-, Chlor- und Nitro-Derivaten mit Methyl-benzolen in Gegenwart von Bortrifluorid fuhrt in den meisten Fallen zu Gemischen von aromatischen Aminen, wobei man z.B. aus 4-Azido-l-methyl-benzol und 1,3-Dimethyl-benzol als Hauptprodukt (2,4-Dimethyl-phenyl)-(4-methyl-phenyl)-amin (67%) neben 4-Methyi-N-(3-methyl-benzyl)-anilin (7,5%) und 4-Methyl-anilin (5%) erhalt, aus l-Azido-4-methyl-benzol und Mesitylen jedoch (4- (Methyl-phenyl)-(2,4,6-trime-thyl-phenyl)-amin (55%) neben nur wenig 2,4,6-Trimethyl-anilin (1%)2. 

Auf ahnliche Weise erhalt man z. B. aus 3,4-Dichlor-N-(2,4,6-trimethyl-benzyliden)-anilin durch Deprotonierung mit Butyl-lithium in Tetrahydrofuran und anschlieBende Umset-zungmit 2-Amino-propan, gefolgt von saurer Hydrolyse, 1-Amino-1-( 3,4-dichlor-phenyl)-2-metkyl-propan (90%)2. 

Analoge reduktive Demethylierungen lassen sich auch mit Natrium-boranat durchfuh-ren, z. B. N,N,N-Trimethyl-anilinium-jodid in Dimethyl-sulfoxid zu N,N-Dimethyl-anilin (96%) und Dodecyl-trimethyl-ammonium-bromid in Phosphorsaure-tris-[dimethylamid] (HMPT) zu 1-Dimethylamino-dodecan (65%)1. 

N -Diphenyl-2,4,6-trinitro-l, 3-pbenylene-diamine or 2,4,6-Trinitro-l,3-dianilinobenzene, C6H5.NH.CeH(N02)3.NH.C8H5, red ndls (from glac acet ac), mp 217°. It was prepd by heating aniline with N-nitro-N,N/,N/-trimethyl-... 

In an application of the Suzuki process, 2-chloroquinoline (141) has been converted into the condensed heterocycle 197 (Scheme 58) (89JHC1589). Thus, metalation, trimethyl borate quench, and hydrolysis affords the stable 3-boronic acid 195 which, upon subjection to cross coupling with ortho-iodo aniline in the presence of Pd(0) catalyst and base, affords the 3-arylquinoline 196. Acid catalysis converts this material into the in-dolo[2,3-f ]quinoline (197) in 35% overall yield. 

ANILINE (continued) 4-Methyl-2-heptene 2,4,4-Trimethyl-2-pentene Diisobutene 1-Nonene... 

Trimethyleneimine. See Azetidine A518-R N-(Trimethylolmethane)-aniline. See Aniiinotrimethyloimechane A44I-L 2,4,6-Trimethyl-1,3,5-trioxane. See... 

In the Vilsmeier formylation of iV-( 3-hydroxyethyl)anilines the hydroxyl group is simultaneously replaced by chlorine [60], The resulting aldehydes condense with l,3,3-trimethyl-2-methyleneindoline to form very brilliant dyes [61], With 4-(W-methyl-iV- 3-chloroethylamino)benzaldehyde a commercial dye is obtained. A methyl group in the 2-position to the methine chain produces a bluish-red color (27). 

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