1.3.5- Trimethyl-2-nitrobenzene

C9H11N02 1,3,5-trimethyl-2-nitrobenzene 603-71-4 528.15 46.595 1,2 17087 C9H120 4-methoxy-1,2-dimethyl benzene 4685-47-6 475J J1501 1 9... 

Trimethyl-3H-indole Trimethyl(4-methylphenyl)silane 1,4,5-Trimethylnaphthalene 1,3,5-Trimethyl-2-nitrobenzene... 

The conductometric titrations of the non-conducting solution of trimethyl-tin iodide in nitrobenzene (at c 7.10 2) with different donors reveal that conducting solutions are formed. The molar conductivity at a given mole ratio D (CH3 )3 SnI generally increases with increasing donicity of the donor10 (Fig. 9),... 

Triazine containing polysulfides having high molecular weights have been readily synthesized by the phase-transfer catalyzed polycondensation of 6-diethylamino or dibutylamino-l,3,5-triazine-2,4-dithiols with 1,10-dibromodecane in the presence of cetyl trimethyl ammonium bromide in a nitrobenzene-aqueous alkaline solution system <99MI294>. 

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

A mixture of 59.5 g (0.2 mol) 2-(4-methoxybenzyl)-l,3,3-trimethyl-4-piperidone hydrochloride and 53.8 g (0.4 mol) of aluminum trichloride and 54.0 g of nitrobenzene in 1500 ml of dry benzene are boiled under reflux for 1 h. After cooling the reaction mixture is extracted with 750 ml 4 N sodium hydroxide solution, the temperature being maintained below 35°C. The organic phase is separated and extracted with 750 ml 1 N hydrochloric acid. The acid aequeous phase is rendered alkali by the addition of 100 ml 25% ammonia and extracted three times with 250 ml chloroform. The collected chloroformic phases are dried with sodium sulfate and evaporated under reduced pressure. The residue, 46.7 g, is converted into the hydrochloride by reaction with iso-propanol/HCI and crystallized from a mixture of methanol and ethylacetate. 44.6 g of the 5-hydroxy-2 -methoxy-2,9,9-trimethyl-6,7-benzomorphan hydrochloride are obtained, melting point 233-236° C (dec.). 

It is only fair when reviewing syntheses to mention unsuccessful reactions so as to outline any shortcomings of a particular reagent, and this has been done throughout this review. Sah et al. have recently reported that reaction of the metallated lithium phenolate (31) with either nitrobenzene or bis(trimethyl-silyl) peroxide gave only starting material, while reaction with trimethyl borate followed by oxidation furnished a complex mixture. 

In liquid-phase reactions such effects may be much more pronounced. It is frequently found that a change in solvent may change the rate of a liquid reaction, in some cases by many orders of magnitude. <> A most spectacular example of this is the reaction of ethyl iodide with trimethyl-amiiie to form the quaternary salt. The reaction rate is almost 1000 times greater in nitrobenzene than in cyclohexane under comparable conditions. 

Fig. 1. Linear correlation between NMR chemical shifts at infinite dilution of CF3I in various electron pair donor solvents and donicity (DN), referred to CCI3F as external reference. NB, nitrobenzene BN, benzonitrile AN, acetonitrile PDC, propanediol-1, 2-carbonate THF, tetrahydrofuran DMF, dimethylformamide EC, ethylene carbonate TMP, trimethyl phosphate DMA, N,N-dimethylacetamide DMSO, dimethylsulfoxide HMPA, hexamethyl-phosphoric amide.

O) 1—benzoyl fluoride 2—nitromethane 3—nitrobenzene 4—benzo-nitrile S—acetonitrile 6—propanediol-1, 2-carbonate 7—ethylene sulfite 8—Water 9—trimethyl phosphate 10—dimethylformamide 11—N, N-di-methylaoetamide 12—dimethyl sulfoxide 13—hexamethylphosphoric amide. 

The acid had already been prepared by Spath, but a more convenient route was discovered. When pyrogallol trimethyl ether is condensed with succinic anhydride in nitrobenzene with aluminum chloride it can yield either /3-2-hydroxy-3,4-dimethoxybenzoylpropionic acid (XLVIII),... 

The formation of an insertion product of diphenylketene into the B-S bond in trimethyl thioborate is evidenced by the isolation of Ph2CHCOSMe after hydrolysis Insertion of ketene into C-H, C-0 and C-Cl bonds is also encountered. For example, reaction of triphenylmethyl chloride with ketene in a nonpolar solvent, in the presence of aluminum chloride, affords the insertion product 336. In nitrobenzene, the reaction proceeds without the added catalyst . 

According to Gert Kobrich and Peter Buck, phenyllithium reacts with nitrobenzene to afford, along with azobenzene and diphenylamine, phenol in almost quantitative yield. A few other aryllithiums, including [2,2]paracyclophane-2,3 -diyldilithium, have also been converted in this way into the phenols, if in poor yield. 2,6-Dimethyl-1-nitrobenzene seems to secure better results but is not readily available. Perhaps the commercial 2,4,6-trimethyl-1-nitrobenzene (nitromesitylene) could serve as a surrogate. 

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