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
ECHA InfoCard 100.000.849
EC Number
  • 200-933-5
UNII
  • InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3 checkY
    Key: IVDFJHOHABJVEH-UHFFFAOYSA-N checkY
  • CC(C)(O)C(C)(C)O
  • CC(C)(O)C(C)(C)O
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
 Pinacolone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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

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