Pinacol

Pinacol

Names
IUPAC name 2,3-dimethyl-2,3-butanediol
Other names tetramethylethylene glycol, 1,1,2,2-tetramethylethylene glycol, pinacone
Identifiers
CAS Registry Number	76-09-5 Y
ChemSpider	21109330 Y
InChI InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3 Y Key: IVDFJHOHABJVEH-UHFFFAOYSA-N Y
Jmol-3D images	Image Image
SMILES CC(C)(O)C(C)(C)O CC(C)(O)C(C)(C)O
Properties
Chemical formula	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
MSDS	External MSDS
S-phrases	S24 S25
Flash point	77 °C (171 °F; 350 K)
Related compounds
Related compounds	Pinacolone
Except where noted otherwise, data is 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

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

• Semipinacol rearrangement

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