Pinacol
Appearance
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Names | |
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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)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.849 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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 | |
GHS labelling: | |
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Warning | |
H228, H315, H319, H335 | |
P210, P240, P241, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, P501 | |
Flash point | 77 °C (171 °F; 350 K) |
Safety data sheet (SDS) | External MSDS |
Related compounds | |
Related compounds
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Pinacolone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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; Collected Volumes, vol. 1, p. 459.
- ^ G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses; Collected Volumes, vol. 1, p. 462.
- ^ Tatsuo Ishiyama; Miki Murata; Taka-aki Ahiko; Norio Miyaura (2004). "Bis(pinacolato)diboron". Organic Syntheses; Collected Volumes, vol. 10, p. 115.