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| Names | |
|---|---|
| Preferred IUPAC name 2,3-Dimethylbutane-2,3-diol | |
| Other names 2,3-Dimethyl-2,3-butanediol Tetramethylethylene glycol 1,1,2,2-Tetramethylethylene glycol Pinacone | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.849  |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
Chemical formula | C6H14O2 |
| Molar mass | 118.174 g/mol |
| Appearance | White solid |
| Density | 0.967 g/cm3 |
| Melting point | 40 to 43 °C (104 to 109 °F; 313 to 316 K) |
| Boiling point | 171 to 173 °C (340 to 343 °F; 444 to 446 K) |
| Hazards | |
| Safety data sheet | External MSDS |
| GHS pictograms | ) ) |
| GHS Signal word | Warning |
GHS hazard statements | H228, H315, H319, H335 |
GHS precautionary statements | P210, P240, P241, P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P405, P501 |
| Flash point | 77 °C (171 °F; 350 K) |
| Related compounds | |
Related compounds | Pinacolone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms.
Preparation
It may be produced by the pinacol coupling reaction from acetone:[1]
)
Reactions
As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating with sulfuric acid:[2]
)
Pinacol can be used with borane and boron trichloride to produce useful synthetic intermediates such as pinacolborane, bis(pinacolato)diboron,[3] and pinacolchloroborane.
See also
References
- ^ Roger Adams and E. W. Adams. "Pinacol Hydrate". Organic Syntheses.; Collective Volume, 1, p. 459
- ^ G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses.; Collective Volume, 1, p. 462
- ^ Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004). "Bis(pinacolato)diboron". Organic Syntheses.; Collective Volume, 10, p. 115