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| | Pinacol Basic information |
| Product Name: | Pinacol | | Synonyms: | TETRAMETHYLETHYLENE GLYCOL;PINACOL;2,3-DIMETHYLBUTANEDIOL-2,3;PINACOL pure;2,3-Dimethyl-2,3-butanediol, Tetramethylethylene glycol;2,3-Dimethyl-2,3-butanediol (Pinacol);Pinacol,2,3-Dimethyl-2,3-butanediol, Tetramethylethylene glycol;Frequency that alcohol | | CAS: | 76-09-5 | | MF: | C6H14O2 | | MW: | 118.17 | | EINECS: | 200-933-5 | | Product Categories: | Acetone series;76-09-5 | | Mol File: | 76-09-5.mol |  |
| | 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) | | Fp | 171 °F | | storage temp. | Inert atmosphere,Room Temperature | | solubility | alcohol: freely soluble | | form | Crystalline Low Melting Solid | | pka | 14.80±0.29(Predicted) | | 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 | | 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) |
| | Pinacol Usage And Synthesis |
| Chemical Properties | white solid | | Occurrence | Has apparently not been reported to occur in nature. | | 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. | | 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. | | 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 | | Definition | ChEBI: A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.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 Preparation Products And Raw materials |
| Raw materials | Mercury chloride | | Preparation Products | Pinacolone-->3-MORPHOLINOPHENYLBORONIC ACID PINACOL ESTER-->4-(PYRROLIDIN-1-YLMETHYL)BENZENEBORONIC ACID, PINACOL ESTER 97%1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]PYRROLIDINE-->2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->2-[3-(2-FURYL)PHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->Bis(pinacolato)diboron-->1-Methyl-1H-pyrazole-5-boronic acid pinacol ester-->4-((N,N-DIMETHYLAMINO)METHYL)PHENYLBORONIC ACID PINACOL ESTER HYDROCHLORIDE-->4-SULFAMOYLPHENYLBORONIC ACID, PINACOL ESTER-->2-(1-FLUORONAPHTHALEN-4-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->1-Methyl-4-pyrazole boronic acid pinacol ester-->4-Hydroxyphenylboronic acid pinacol ester-->5-AMINOPYRIDINE-2-BORONIC ACID PINACOL ESTER-->2-(2-ISOPROPYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->Allylboronic acid pinacol ester-->Pinacol vinylboronate-->Pinacolborane-->4-Carboxylphenylboronic acid pinacol ester-->Benzenamine, 3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)--->Isopropenylboronic acid pinacol ester-->4-Nitrophenylboronic acid pinacol ester-->2,3-DIMETHYL-1,3-BUTADIENE-->3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine |
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