Pinacol

Pinacol
IUPAC name

2,3-dimethyl-2,3-butanediol
Other names

tetramethylethylene glycol, 1,1,2,2-tetramethylethylene glycol, pinacone
Identifiers
CAS number 76-09-5 Y
ChemSpider 21109330 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H14O2
Molar mass 118.174 g/mol
Appearance White solid
Density solid
Melting point

40–43 °C
Boiling point

171–173 °C (444–445 K)
Solubility in water  ? g/100 ml (?°C)
Hazards
MSDS External MSDS
S-phrases S24 S25
Flash point 77 °C
Related compounds
Related compounds Pinacolone
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pinacol is a white solid organic compound. It is an alcohol that has -OH groups on adjacent carbon atoms on the same side. (i.e., same spatial arrangement).

Contents

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 use with borane and boron trichloride to produce useful synthetic intermediate such as pinacolborane, bis(pinacolato)diboron,[3] and pinacolchloroborane.

See also

References

  1. ^ Roger Adams and E. W. Adams, "Pinacol Hydrate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0459 ; Coll. Vol. 1: 459 
  2. ^ G. A. Hill and E. W. Flosdorf (1941), "Pinacolone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0462 ; Coll. Vol. 1: 462 
  3. ^ Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004), "Bis(pinacolato)diboron", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v77p0176 ; Coll. Vol. 10: 115