Pinacol

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
76-09-5 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:131185 N
ChemSpider 21109330 YesY
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 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).
N verify (what is YesYN ?)
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". Org. Synth.; Coll. Vol., 1, p. 459
  2. G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Org. Synth.; Coll. Vol., 1, p. 462
  3. Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004). "Bis(pinacolato)diboron". Org. Synth.; Coll. Vol., 10, p. 115
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