1- Amino-3,4,5-trimethylbenzene

In a similar way, Kim and Bunnett (1970) demonstrated that the substitution of amino group for iodine in iodotrimethylbenzene proceeds via the ion-radical mechanism, in contrast to the bromo and chloro analogs. The reaction of 5- and 6-halo-l,2,4-trimethylbenzenes with potassium amide in liquid ammonia gives rise to 5- and 6-aminoderivatives. This is the cine-substitution reaction (see Scheme 4.12). 

An attempt to generate an amino-aryl carbene 154 from the alkylated phenanthridinium salt 153 (Equation 78) <2006TL531> was unsuccessful due to steric interactions. The actual reaction with a variety of strong, sterically hindered bases/nucleophiles is shown (Equations 79-81). The mesityllithium products proved that a carbene intermediate is not possible. Unlike /-butyl alcohol and hexamethyldisilazane, trimethylbenzene, the conjugate acid of mesityllithium, is not prone to carbene insertion reactions. Electronically this is explained by the planar nature of 153 which serves to lower the lowest unoccupied molecular orbital (LUMO) energy of the iminium moiety. 

The photostimulated reaction of l-bromo-2,4,6-trimethylbenzene (a substrate with no o-hydrogen atoms in order to avoid the benzyne mechanism) with NH2 ions gave 1-amino-2,4,6-trimethylbenzene (70%) and the reduction product 1,3,5-trimethylbenzene (6%). This reaction did not occur in the dark221. By competition experiments of NH2 ions with Ph2P" ions toward 2,4,6-trimethylphenyl radicals, it was found that Ph2P ions are 6.4 times more reactive than NH2 ions221, whereas NH2 ions are twice more reactive than acetone enolate ions toward the same radical in liquid ammonia222. 

SYNS AMINOMESITYLENE 2-AMINOMESITYL-ENE 1-AMINO-2,4,6-TRIMETHYLBENZEN (CZECH) 2-AMINO-l,3,5-TRIMETHYLBENZENE MESIDIN-... 

SYNS AMINOMESITYLENE HYDROCHLORIDE 2-AMINOiMESITYLENE HYDROCHLORIDE 2-AMINO-1,3-5-TRIMETHYLBENZENE HYDROCHLORIDE MESIDINE HYDROCHLORIDE MESITYLAMINE HYDROCHLORIDE 2,4,6-TRIMETHYLBENZENAMINE HYDROCHLORIDE... 

AMINO-l,3-5-TRIMETHYLBENZENE HYDROCHLORIDE see TLHOOO AMINOUNDECANOIC ACID see AMWOOO 11-AMINOUNDECANOIC ACID see AMWOOO 11-AMINOUNDECYLIC ACID see AMWOOO AMINOURACIL MUSTARD see BIA2S0 AMINOUREA see HGUOOO AMINOUREA HYDROCHLORIDE see SBW500... 

There are numerous isomers of the multiply methylated anilines, most of which have been ignored by the thermochemical community. Of the six possible ring-only methylated species, the sole species to be studied is the 2,4,5-trimethylaniline (the earlier-named pseudocumidine) in the very old Reference 23. The solid-phase enthalpy of formation is —110 k mol 1. The enthalpy of formation of the corresponding hydrocarbon, 1,2,4-trimethylbenzene (the earlier-named pseudocumene), is —25 kJ rnol 1 using a temperature-uncorrected fusion enthalpy. The resulting amino/hydrogen difference is 85 kJmol-1, an altogether unreasonable value. 

Sufficiently high exposures to alkylbenzenes—such as //-diethylbenzene, -triethylbenzene, -trimethylbenzene, and isopropylbenzene—can produce adverse motor and sensory effects in rats after inhalation. Gagnaire et al. (1990) reported decreased motor and sensory conduction velocities and decreased amplitude of the sensory action potential of the tail nerve in rats exposed repeatedly to a mixture of diethylbenzene and its major metabolite, 1,2-diacetylbenzene (DAB). In the rat, 1,2-diethylbenzene was about 5 times more potent a neurotoxicant than -hexane (Gagnaire et al. 1990). Spinal-cord axonal swelling with partial demyelination has been associated with DAB exposure in rats (Kim et al. 2001). The neurotoxicity of 1,2-diethylbenzene appears to be related to formation of protein complexes reaction with amino acids of proteins to form pyrolated polymers that lead to protein cross links. 

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... 

CAS 137-17-7 EINECS/ELINCS 205-282-0 Synonyms 1-Amino-2,4,5-trimethylbenzene Aniline, 2,4,5-trimethyl- Benzenamine, 2,4,5-trimethyl- Pseudocumidine Psi-cmidine 1,2,4-Trimethyl-5-aminobenzene 2,4,5-Trimethylbenzenamine Empirical C9H13N Formula (CH3)3C6H2NH2 Properties Wh. cryst. or beige powd. sol. in DMSO, 95% ethanol, acetone, alcohol, ether sol. 

The amino acid complexes [(q -arene)Ru(aa)Cl], where aa = N,0-chelated amino acid, undergo rapid epimerization even at temperatures below 0 °C [66,67]. Similar lability and epimerization has been found for sahcylaldiminato complexes [68]. In contrast, [(ri -p-cymene)Ru(imine)Cl] complexes are configurationally stable unless heated to high temperatures in polar solvents [69]. Configurationally-stable half sandwich Ru(If) arene complexes are ofmuch interest as potential asymmetric catalysts (e.g. for Diels-Alder and Mukaiyama reactions) [63]. The chloride ligand is usually removed in order to allow the complex to act as a Lewis add catalyst and exchange ofcoordinated water on [(r -l,3,5-trimethylbenzene)Ru(pyridyloxazoline-N,N )(H20)] is slow on the NMR timescale in acetone-water [70]. Chiral chloro arene Ru(II) catalysts for asymmetric transfer hydrogenation can be activated in situ by treatment with KOH in 2-propanol [71]. 

When the arenediamines 2,4,6-trimethylbenzene-l,3-diamine and 2,2, 6,6 -tetramethyl-4,4 -methylenediphenylamine were treated under the same reaction conditions with 1.4 equivalents of B0C2O and 1.0 equivalent of DMAP per amino group in acetonitrile at room temperature Method A, work-up with sulfuric acid), 2,4,6-tnmethylbenzene-l,3-diisocyanate 339 and 2,2, 6,6 -tetramethyl-4,4 -meth-ylenediphenyl isocyanate 340 were obtained in yields of 84% and 93%, respectively. Arenediyl diisocyanates play a very important role as monomers for the industrial synthesis of polyurethanes and polyureas [226]. 

---