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
CAS Number	76-09-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:131185 ;
ChEMBL	ChEMBL3289669;
ChemSpider	21109330 ;
ECHA InfoCard	100.000.849
EC Number	200-933-5;
PubChem CID	6425;
UNII	527QE7I5CO ;
CompTox Dashboard (EPA)	DTXSID3058793 ;
	InChI InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3 Key: IVDFJHOHABJVEH-UHFFFAOYSA-N ;
	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
	GHS labelling:
Pictograms
Signal word	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). verify (what is ?) Infobox references

Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms.

Preparation[edit]

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.

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

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^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:131185^Y
ChEMBL	ChEMBL3289669
ChemSpider	21109330^Y
ECHA InfoCard	100.000.849
EC Number	200-933-5
PubChem CID	6425
UNII	527QE7I5CO^Y
CompTox Dashboard (EPA)	DTXSID3058793
InChI InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3^Y Key: IVDFJHOHABJVEH-UHFFFAOYSA-N^Y
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
GHS labelling:
Pictograms
Signal word	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). N verify (what is ^YN ?) Infobox references