Chemistry: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
ChEMBL
ChemSpider
EC Number
  • 200-933-5
UNII
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
GHS pictograms GHS05: CorrosiveGHS07: Harmful
GHS Signal word Warning
H228, H315, H319, H335
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).
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Infobox references
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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]

Pinacol coupling of acetone.png

Reactions

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

References

  1. Roger Adams and E. W. Adams. "Pinacol Hydrate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv1p0459. ; Collective Volume, 1, pp. 459 
  2. G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV1P0462. ; Collective Volume, 1, pp. 462 
  3. Tatsuo Ishiyama; Miki Murata; Taka-aki Ahiko; Norio Miyaura (2004). "Bis(pinacolato)diboron". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=v77p0176. ; Collective Volume, 10, pp. 115