O-tolyl chloride

Toluic acids, ml42 thru 144 o -Tolunitrile, p82 / -Tolylacetamide, m374 Tolyl bromide, b431 o -Tolyl chloride, b90 Tolyl chlorides, c255 thru c257... 

Synonyms 2-Chloro-l-methylbenzene 2-chlorotoluene Halso 99 o-tolyl chloride... 

In the presence of low reactive aromatic substrates such as o-tolyl chloride, it has been shown that production of the aromatic zinc occurs only at the potential at which the zinc(II) bipyridine is reduced, i.e. at about —1.4 V/SCE. Furthermore, the nickel(II) complex is also reduced at this potential value. In this case, the formation of either a bi-metallic species, or a cluster (18), intermediary combining Ni(0) and Zn(0) via the bipyridine ligand is suggested. This complex would react with the aromatic chloride to produce the corresponding ArZnCl along with the regeneration of the nickel catalyst. 

SYNS 2-CHLORO-l-METHYLBENZENE (9CI) 2-CHLOROTOLUENE H.USO 99 l-METHYL-2-CHLOROBENZENE 2-METHYLCHLOROBENZENE o-TOLYL CHLORIDE... 

Thallium di-o-tolyl chloride,— This compound is prepared by the action of thallie chloride on magnesium o-tolyl bromide, then boiling the product obtained with dilute hydrochloric acid. It crystallises from pyridine in slender, microscopic needles, which do not melt at 300° C. and are insoluble in all organic solvents. 

Tin tri-o-tolyl chloride crystallises from alcohol in thick, colourless prisms, M.pt. 99 5° C. The bromide forms compact, rhombic plates, M.pt. 99-5° G., and the iodide rhombic crystals, M.pt, 119 5° C. The solubilities of these three compounds are similar to the corresponding para compounds. 

Conducted at 22-70 C with either NaOf-Bu, or KOH/HjO/tol. with cat. C16H33NMe3Br at 90 C. b Not broadly applicable, limited to o-tolyl chloride.c 120 °C.a Not broadly applicable, limited to t-BuNH2 or (Ad)NH2. Not broadly applicable, limited to BnNH2 or hexylamlne with o-lolyl chloride. 22-80 C. Used K3P04 in DME if R1 is base sensitive. 0 Used UHMDS if R1 a acidic. h <70% yields for EWG and EDG.1 22 °C in DME... 

The Buchwald series of bulky phosphines containing the tunable bi-aryl moiety have also been shown to allow for the efficient animation of aryl chlorides as well.57 In particular, Pd/L3 catalyzed the reaction between secondary cyclic amines and most aryl chlorides at 80 °C, Secondary acyclic amines and anilines tend to couple best with neutral to electron rich aryl chlorides. Primary aliphatic amines are quite limited to either the amination of o-tolyl chlorides, or more activated primary amines such as benzyl amine. A better ligand for this transformation was reported to be L4 as the amination could be conducted at room temperature in many cases.58 Base sensitive R1 required the use of K3PO4 rather than NaOf-Bu. Most amines work well with this catalyst system, except for unactivated primary aliphatic amines (e.g., n-hexyl amine). Allyl amine, hydrazines, imines, benzyl amine, and (EtO)2CH2NH2 all couple well with aryl chlorides under the... 

Synonyms 1-Chloro-2-methylbenzene 2-Chloro-1-methylbenzene 2-Chlorotoluene 1-Methyl-2-chlorobenzene 2-Methylchlorobenzene OCT Orthochlorotoluene o-Tolyl chloride Definition Major isomer of monochlorotoluene Empirical C7H7CI... 

Tolyl chloride. See Benzyl chloride o-Tolyl chloride. See o-Chlorotoluene... 

Toluene sulfochloride - 662 Toluene-isooctane mixture - 61 Toluene-kerosene mixture - 262 Toluenesulfonic acid - 38, 45, 51, 167, 178, 214, 373, 374, 377, 382, 404, 411, 718, 788 Toluenesulfonyl chloride - 770 Toluene vapor - 214 Toluic acid - 597, 788 Toluic acid, meta 718 Toluidines - 628 o-Tolyl chloride - 214 Tomato products (see Foods)... 

Figure 11.4 shows the relationship between efficiency and concentration of some thiourea derivatives and gelatin in the pickling of cold-reduced and annealed strip in 6% w/w sulphuric acid at 85°C. The thiourea derivatives, diluted with sodium chloride, gelatin and a wetting agent, are used commercially. Mono- and di-o-tolyl thioureas are stable in this pickle for at least 50 h, but diphenyl thiourea and gelatin decompose after four or five hours. 

Tri-o-tolyl phosphate Turpentine Vinyl acetate Vinyl bromide Vinyl butanoate Vinyl chloride 4-Vinyl-1 -cyclohexene Vinyl fluoride Vinylidene m-Xylene o- Xylene p- Xylene... 

Although the Sonogashira reaction is normally performed with a copper cocatalyst, a copper-free, one-pot procedure for direct coupling with l-aryl-2-trimethylsilylacetylenes has been developed <2005T2697>. The procedure uses a mixture of palladium acetate and tri(o-tolyl)phosphine as catalyst in the presence of tetra- -butylammonium chloride... 

Di-o-tolyl methyl tellurium chloride,2 (C7H7)2(CH3)TeCl, is obtained by boiling the corresponding iodide with silver chloride and water. It separates from water as four-sided plates containing two molecules of water of crystallisation, melting at 93° C. and again at 148° C. from chloroform it crystallises with half a molecule of chloroform, and melts at 155° to 156° C. The basic zinc chloride double salt melts with decomposition at 186° to 187° C. 

Vinyl iodides are considerably more reactive than bromides in the vinylations. It may be presumed that chlorides are not generally useful, with one exception noted below, since they have not been employed in the reaction. The bromides are usually reacted with a palladium acetate-triphenyl- or tri-o-tolyl-phos-phine catalyst at about 100 C. The reaction will occur without the phosphine if a secondary amine is present. Vinyl iodides will react in the absence of a phosphine even with only a tertiary amine present.48 37 The iodides are so reactive, in fact, that reactions occur even at room temperature if potassium carbonate is the base and tetra-zi-butylammonium chloride is used as phase transfer agent in DMF solution when palladium acetate is the catalyst.88... 

Tolunitrile has also been prepared from o-toluidine by conversion into o-tolyl isothiocyanate and the boiling of this under a reflux condenser 4 />-tolunitrile has been prepared by distilling />-toluic acid with potassium thiocyanate 5 and a mixture of the two has been produced by the interaction of toluene, mercury fulminate, and aluminium chloride.6... 

Ethyl, methyl > m-tolyl, phenyl >/>-tolyl, p-ethoxyphenyl, p-methoxy-phenyl, o-tolyl, o-ethoxyphenyl, o-methoxyphenyl > cyclohexyl, mesityl, 1-naphthyl. The reaction is catalyzed by metal salts such as aluminum chloride. 

---