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Pinacol

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CAS:76-09-5
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Pinacol Basic information
Product Name:Pinacol
Synonyms:TETRAMETHYLETHYLENE GLYCOL;PINACOL;2,3-DIMETHYLBUTANEDIOL-2,3;Pinakol;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
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 Structure
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
pka14.80±0.29(Predicted)
form Crystalline Low Melting Solid
color White
Odorat 100.00 %. woody earthy patchouli warm bread
Odor Typewoody
Water Solubility Soluble in hot water, alcohol, and diethyl ether.
Sensitive Hygroscopic
Merck 14,7439
BRN 1340501
Henry's Law Constant1.0×102 mol/(m3Pa) at 25℃, Wang et al. (2017)
Dielectric constant7.4(24℃)
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, strong acids.
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3
InChIKeyIVDFJHOHABJVEH-UHFFFAOYSA-N
SMILESCC(C)(O)C(C)(C)O
LogP0.540
CAS DataBase Reference76-09-5(CAS DataBase Reference)
NIST Chemistry Reference2,3-Butanediol, 2,3-dimethyl-(76-09-5)
EPA Substance Registry System2,3-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
3
TSCA TSCA listed
HS Code 29053990
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
2,3-Dimethyl-2,3-butanediol English
ACROS English
SigmaAldrich English
ALFA English
Pinacol Usage And Synthesis
Chemical Propertieswhite solid
OccurrenceHas apparently not been reported to occur in nature.
Usespinacol 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.
UsesPinacol 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.
PreparationBy the bimolecular reduction of acetone.
DefinitionChEBI: 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 evaluationBoth 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 DescriptionThe pinacol coupling reaction with the inorganic electride [Ca2N](+)·e() as an electron donor in organic solvents was studied.
MetabolismPinacol 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 MethodsThe 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.]
Tag:Pinacol(76-09-5) Related Product Information
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