Dibenzylamine

Chemical Properties

colorless to light yellow oily liquid with ammonia odor. soluble in ethanol and ether, insoluble in water.

Uses

Dibenzylamine is used to prepare rubber accelerator for the vulcanization process and reaction-stoppers. Dibenzylamine type accelerators reduce nitrosamine production in the compounding process. It is also used to produce dibenzyl-nitroso-amine.

Definition

ChEBI: Dibenzylamine is an aromatic amine.

Preparation

Dibenzylamine is obtained by the reaction of benzyl chloride and liquid ammonia in ethanol.

Application

Dibenzylamine is an important organic synthesis intermediate, mainly used to produce efficient and non-toxic vulcanization accelerators tetrabenzylthiuramdisulfide (TBZTD) and zinc dibenzyldithiocarbamate (ZBEC). Synthesize penicillin and curing agent for rubber and plastic curing, and can be used in the detection of cobalt, cyanate, and iron.

Biological Functions

Dibenzylamine (DBA) has anticonvulsant effects. It can block NMDA-evoked currents in a concentration and voltage-dependent manner. This conclusion was researched in an audiogenic seizure-susceptible mouse model. It possesses antiproliferative properties and could be of interest for the development of new antitumor drugs.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 4633, 1985 DOI: 10.1016/S0040-4039(00)98771-9
The Journal of Organic Chemistry, 60, p. 5969, 1995 DOI: 10.1021/jo00123a041

Hazard

Dibenzylamine is danger.
H302 (99.32%): Harmful if swallowed [Warning Acute toxicity, oral]
H314 (57.43%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H315 (42.57%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (42.57%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H412 (32.43%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Purification Methods

Purify the amine by distillation in a vacuum. It causes burns to the skin. The dihydrochloride has m 265-266o (from MeOH/HCl), and the tetraphenyl boronate has m 129-133o. [Bradley & Maisey J Chem Soc 247 1954, Hall J Phys Chem 60 63 1956, Donetti & Bellora J Org Chem 37 3352 1972, Beilstein 12 IV 2179.]