Tert-Butyl chloride

Tert- butyl chloride

Colorless liquid

Liquid

0.84 g · cm -3 ( 20 ° C)

-27.1 ° C

51 ° C.

317 hPa ( 20 ° C)

Practically insoluble in water

1.3857 (20 ° C)

Risk

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2-chloro -2-methyl propane (t- butyl ) is a colorless, water-white liquid. It belongs to the group of halogenated alkanes and is the simplest tertiary chloroalkane.

Production

The synthesis of 2- chloro-2- methylpropane succeed in very good yield by nucleophilic substitution ( SN1 type of reaction ) of tert -butyl alcohol with concentrated hydrochloric acid. The product is purified by drying and subsequent distillation.

As a by- product of this reaction is caused by loss of a proton from the intermediate carbenium ion 2- methylpropene ( isobutene ). Industrial preparation can be carried out as a gas phase reaction between isobutene and hydrogen chloride in the presence of alumina at 100 ° C.

Properties

Physical Properties

2-chloro -2-methyl propane is a colorless, mobile liquid. It has 0.842 g/cm3 with a lower density than water. It is quite volatile and boils at about 51 ° C. Most organic solvents are miscible in all proportions.

Chemical Properties

As the tertiary alkyl halide, 2-chloro -2-methyl propane reacts due to steric hindrance as compared to other haloalkanes rather slow. SN2 reactions are hardly possible. In the reaction with bases with elimination of a proton from one of the methyl groups, the elimination (E2 ) for 2-methylpropene is done ( isobutene ).

Under the action of anhydrous Lewis acids such as aluminum chloride or iron (III ) chloride, there is the elimination of a chloride ion in the formation of the tert- butyl cation which can act as an electrophile, alkylating.

Water reacts with tert. Butyl chloride slowly hydrolytically in a nucleophilic substitution (SN1 reaction) to form tert. Butanol, hydrogen ions and chloride ions. This reaction can be monitored by conductivity measurement, since the concentration of the ions formed increases more and more and at the same rate, the concentration of tert. Butyl chloride decreases. The evaluation of this measurement shows that in this case, a 1st order reaction is present.

Use

In the organic- chemical synthesis of 2-chloro -2- methylpropane is used as the electrophile, in Friedel- Crafts alkylation to bind a tert- butyl group to an aromatic. Starting from benzene possible catalyzed by anhydrous aluminum chloride, the preparation of tert- butylbenzene.

The initially formed tetrachloroaluminate ion reacts with the split from the aromatic proton to form hydrogen chloride with re-formation of the aluminum chloride, so that only substoichiometric amounts of AlCl3 are required.

Safety

2-chloro -2-methyl propane is highly volatile and flammable. Therefore have to be used under a fume hood. A protective goggles must be worn at work always. During refilling measures against static electricity should be taken.

• Inhalation: Remove exposed person to fresh air.
• In case of skin contact: wash off with plenty of water.
• On contact with eyes: at least 15 minutes, rinse thoroughly with water ( eyewash ). Possibly. Consult an ophthalmologist.
• If swallowed, do not induce vomiting if possible.
• Clean or Remove contaminated clothing immediately.

The substance may cause in chronic Contact liver and kidney damage.