2-хлортолуола

Описание

2-Chlorotoluene can be mineralized completely by Rhodococcus, strain OCT 10 DSM 45596(T). It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol. The oxidation of 2-chlorotoluene is very well catalyzed by the enzymes: toluene dioxygenase of P. putida F1 and chlorobenzene dioxygenase from Burkholderia, strain PS12.

Химические свойства

o-Chlorotoluene is a flammable, colorless liquid with an aromatic odor.

Использование

Solvent and intermediate for organic chemicals and dyes.
2-Chlorotoluene is used for permanganate oxidation to give o-chlorobenzoic acid. It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol.
2-Chlorotoluene can be used as a precursor to synthesize aryl coupling products via palladium-catalyzed Negishi cross-coupling. It can also be used in the Buchwald-Hartwig amination to synthesize arylamines.

Подготовка

The solution of cuprous chloride is cooled in an ice bath 0-5° C temperature. In this cold solution, the 2-methylbenzenediazonium is poured with constant shaking and allowing the mixture to come to room temperature. After about 10 minutes, the mixture gradually warmed with a good shaking.As the temperature rises the brown addition product begins to decompose with the evolution of nitrogen and with the formation of an oily layer of 2-chlorotoluene. When the decomposition reaction is at an end, the mixture is steam distilled, continuing the process only as long as oily droplets are present in the distillate, for the product is not appreciably soluble in water. The layer of 2-chlorotoluene is carefully separated and washed twice with an equal volume of concentrated sulfuric acid, which removes both the 2-cresol and the azo compound. Then 2-chlorotoluene is washed with water in order to remove the inorganic acid. Finally, 2-chlorotoluene is dried over calcium chloride, distilled, using an air condenser and collecting the product boiling at 153-158° C. Pure 2-chlorotoluene boils at 157° C. The yield is 25-30 g.

Experiments in Organic Chemistry, L. F. Fieser, 216, 1941
Highly Selective Oxidative Monochlorination To Synthesize Organic Intermediates: 2-Chlorotoluene, 2-Chloroaniline, 2-Chlorophenol, and 2-Chloro-4-methylphenol

Общее описание

Colorless liquid with an aromatic odor. Denser than water and poorly soluble in water. Hence sinks in water .

Реакции воздуха и воды

Slightly water soluble.

Профиль реактивности

2-Chlorotoluene may be incompatible with strong oxidizing and reducing agents. Also may be incompatible with amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Reacts violently with dimethyl sulfoxide .

Опасность

Toxic by inhalation. Eye, skin, and upper respiratory tract irritant.

Угроза здоровью

Inhalation of vapor may cause respiratory irrtation. Prolonged and repeated vapor exposures may produce systemic toxic effects.

Профиль безопасности

Moderately toxic by unspecified routes. Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-. See also TOLE CHLORIDE and CHLORINATED HYDROCARBONS, AROMATIC.

Возможный контакт

o-Chlorotoluene is widely used as a solvent and intermediate in the synthesis of dyes, synthetic rubber; pharmaceuticals; and other organic chemicals. Used as an insecticide, bactericide.

Перевозки

UN2238 Chlorotoluenes, Hazard Class: 3; Labels: 3-Flammable liquid.

Методы очистки

Dry 2-chlorotoluene for several days with CaCl2, then distil it from Na using a glass helices-packed column. [Beilstein 5 IV 805.]

Несовместимости

Incompatible with acids, alkalis, oxidizers, reducing materials; water

Утилизация отходов

In accordance with 40CFR165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.