Pinacol

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
CAS Number
  • 76-09-5 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:131185 checkY
ChEMBL
  • ChEMBL3289669
ChemSpider
  • 21109330 checkY
ECHA InfoCard 100.000.849 Edit this at Wikidata
EC Number
  • 200-933-5
PubChem CID
  • 6425
UNII
  • 527QE7I5CO checkY
CompTox Dashboard (EPA)
  • DTXSID3058793 Edit this at Wikidata
InChI
  • 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
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
GHS labelling:
Pictograms
 GHS05: CorrosiveGHS07: Exclamation mark
Warning
Hazard statements
 H228, H315, H319, H335
Precautionary statements
 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).
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Infobox references
Chemical compound

Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction.

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