Pinacol
| 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)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
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: | |
| GHS05: CorrosiveGHS07: Exclamation mark | |
| 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 branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction.
Preparation
[edit | edit source]It may be produced by the pinacol coupling reaction from acetone:[1]
File:Pinacol coupling of acetone.png
Reactions
[edit | edit source]As a vicinal diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g., by heating with sulfuric acid:[2]
File:800px-Pinacol rearragement.png
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
[edit | edit source]References
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