Pinacol

Chemical properties

white solid

Occurrence

Has apparently not been reported to occur in nature.

The Uses of Pinacol

pinacol be used as organic intermediates.
The pinacol coupling reaction with the inorganic electride [Ca2N](+)·e(−) as an electron donor in organic solvents was studied.
Pinacol is used in the synthesis of organic reagents such as alkenylphenylphosphonates and alkenylboronates.

The Uses of Pinacol

Pinacol is used in the preparation of synthetic intermediates like pinacolborane, bis(pinacolato)diboron and pinacolchloroborane by reaction with boron trichloride. Further, it plays an important role as an intermediate for biologically active compounds like antiviral, antibacterial, antifungal and antituberculous.

Definition

ChEBI: A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.

Preparation

By the bimolecular reduction of acetone.

Synthesis Reference(s)

Chemistry Letters, 10, p. 1469, 1981
Journal of the American Chemical Society, 98, p. 1986, 1976 DOI: 10.1021/ja00423a067
Tetrahedron Letters, 21, p. 449, 1980 DOI: 10.1016/S0040-4039(00)71429-8

Toxicity evaluation

Both the acute oral LD₅₀ value in rats and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1975). The acute oral LD₅₀ of pinacol for male albino mice was found to be 28-6 mmol/kg (Wenzel & Koff, 1956). Pinacol showed anticonvulsant activity for electroshock seizures and Metrazol? convulsions; the PD 50 values (a measure of the protective dose) determined 15 min after oral administration of pinacol to mice were found to be 16-4 and 3-44 mmol/kg for electroshock and Metrazol convulsions, respectively (Wenzel & Koff, 1956).

General Description

The pinacol coupling reaction with the inorganic electride [Ca₂N](+)·e(?) as an electron donor in organic solvents was studied.

Metabolism

Pinacol forms a glucuronide in the rabbit (Williams, 1959), and was found highly conjugated with glucuronic acid in the urine of chinchilla rabbits following oral administration of 1.0-1.5 g pinacol/kg body weight (Gessner, Parke & Williams, 1960). Pinacol was not utilized to any significant extent by endocrine tissues from human placenta, rat ovary, rat testis or rat adrenal gland (Ferguson, Baillie, Caiman & Hart, 1966).

Purification Methods

The hydrate is rendered anhydrous by azeotropic distillation of water with *benzene. Recrystallise it from *benzene or toluene/pet ether, absolute EtOH or dry diethyl ether. It recrystallises from water to give the hexahydrate. [Beilstein 1 IV 2575.]