Pinacol
From Wikipedia, the free encyclopedia
| Pinacol | |
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2,3-dimethyl-2,3-butanediol |
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Other names
tetramethylethylene glycol, 1,1,2,2-tetramethylethylene glycol, pinacone |
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| Identifiers | |
| CAS number | 76-09-5  |
| ChemSpider | 21109330 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H14O2 |
| Molar mass | 118.174 g/mol |
| Appearance | White solid |
| Density | solid |
| Melting point |
40–43 °C |
| Boiling point |
171–173 °C (444–445 K) |
| Solubility in water | ? g/100 ml (?°C) |
| Hazards | |
| MSDS | External MSDS |
| S-phrases | S24 S25 |
| Flash point | 77 °C |
| Related compounds | |
| Related compounds | Pinacolone |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Pinacol is a white solid organic compound. It is an alcohol that has -OH groups on adjacent carbon atoms on the same side. (i.e., same spatial arrangement).
Contents |
[edit] Preparation
It may be produced by the pinacol coupling reaction from acetone:[1]
[edit] 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 use with borane and boron trichloride to produce useful synthetic intermediate such as pinacolborane, bis(pinacolato)diboron,[3] and pinacolchloroborane.
[edit] See also
[edit] References
- ^ Roger Adams and E. W. Adams, "Pinacol Hydrate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0459; Coll. Vol. 1: 459
- ^ G. A. Hill and E. W. Flosdorf (1941), "Pinacolone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0462; Coll. Vol. 1: 462
- ^ Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004), "Bis(pinacolato)diboron", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v77p0176; Coll. Vol. 10: 115
