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HomeProduct name listPinacol

Pinacol

Synonym(s):2,3-Dimethyl-2,3-butanediol;Pinacol;Tetramethylethylene glycol

  • CAS NO.:76-09-5
  • Empirical Formula: C6H14O2
  • Molecular Weight: 118.17
  • MDL number: MFCD00004462
  • EINECS: 200-933-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:57
Pinacol Structural

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ChEBI: A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.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

Properties of Pinacol

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
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.
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 for Pinacol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H303:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H320:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P321:Specific treatment (see … on this label).
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for Pinacol

InChIKey IVDFJHOHABJVEH-UHFFFAOYSA-N

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