Pinacol

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Pinacol
Pinacol
Ball-and-stick model of 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)
ChEBI
ChemSpider
ECHA InfoCard 100.000.849
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
Safety data sheet External MSDS
S-phrases (outdated) S24 S25
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).
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Infobox references

Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms.

Preparation[edit]

It may be produced by the pinacol coupling reaction from acetone:[1]

Pinacol coupling of acetone.png

Reactions[edit]

As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating with sulfuric acid:[2]

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]

References[edit]

  1. ^ Roger Adams and E. W. Adams. "Pinacol Hydrate". Organic Syntheses. ; Collective Volume, 1, p. 459 
  2. ^ G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses. ; Collective Volume, 1, p. 462 
  3. ^ Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004). "Bis(pinacolato)diboron". Organic Syntheses.  ; Collective Volume, 10, p. 115