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 ;
	show InChI
	show SMILES
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
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H228, H315, H319, H335
GHS precautionary statements	P210, P240, P241, P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P405, P501
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).
	(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[]

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 .

^ Roger Adams and E. W. Adams. "Pinacol Hydrate". Organic Syntheses.; Collective Volume, 1, p. 459
^ G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses.; Collective Volume, 1, p. 462
^ Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, and Norio Miyaura (2004). "Bis(pinacolato)diboron". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 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
show InChI InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3^Y Key: IVDFJHOHABJVEH-UHFFFAOYSA-N^Y
show 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
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H228, H315, H319, H335
GHS precautionary statements	P210, P240, P241, P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P405, P501
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 (what is ^YN ?)
Infobox references