Pinacol Chemical Properties

Melting point:

40-43 °C (lit.)

Boiling point:

171-172 °C/739 mmHg (lit.)

Density 

0.967 g/cm3 (20℃)

refractive index 

1.4347 (estimate)

Flash point:

171 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

alcohol: freely soluble

pka

14.80±0.29(Predicted)

form 

Crystalline Low Melting Solid

color 

White

Odor

at 100.00 %. woody earthy patchouli warm bread

Odor Type

woody

Water Solubility 

Soluble in hot water, alcohol, and diethyl ether.

Sensitive 

Hygroscopic

Merck 

14,7439

BRN 

1340501

Dielectric constant

7.4（24℃）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, strong acids.

InChIKey

IVDFJHOHABJVEH-UHFFFAOYSA-N

LogP

0.540

CAS DataBase Reference

76-09-5(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Butanediol, 2,3-dimethyl-(76-09-5)

EPA Substance Registry System

2,3-Butanediol, 2,3-dimethyl- (76-09-5)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

38-36/37/38-11

Safety Statements 

37-37/39-26

WGK Germany 

2

RTECS 

EK1720000

F 

3

TSCA 

Yes

HS Code 

29053990

MSDS

• Language:English Provider:2,3-Dimethyl-2,3-butanediol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Pinacol Usage And Synthesis

Chemical Properties

white solid

Occurrence

Has apparently not been reported to occur in nature.

Uses

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.

Uses

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.

Preparation

By the bimolecular reduction of acetone.

Definition

ChEBI: A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.

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.]

Pinacol(76-09-5)Related Product Information

• Ethylene glycol diacetate
• Pinacolone
• 1-Phenyl-1,2-ethanediol
• Dimethyl carbonate
• 2-Methyl-2,4-pentanediol
• 2-Butyne-1,4-diol
• Dimethyl fumarate
• Triethylene glycol
• DOWANOL(TM) PNB
• Diethylene glycol
• Polyethylene Glycol
• Dimethyl ether
• ETHYLENE GLYCOL DISTEARATE
• Benzopinacole
• Dimethyl sulfoxide
• FARNESOL
• N,N-Dimethylformamide
• ETHANE