Pinacol
{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 433731685
|Name = Pinacol
|ImageFile = Pinacol-2D-skeletal.png
|ImageName = Pinacol
|ImageSize = 160px
|ImageFile1 = Pinacol-1-from-xtal-3D-bs-17.png
|ImageSize1 = 160px
|ImageName1 = Ball-and-stick model of pinacol
|PIN = 2,3-Dimethylbutane-2,3-diol
|OtherNames = 2,3-Dimethyl-2,3-butanediol
Tetramethylethylene glycol
1,1,2,2-Tetramethylethylene glycol
Pinacone
|Section1={{Chembox Identifiers
|SMILES = CC(C)(O)C(C)(C)O
|CASNo = 76-09-5
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 527QE7I5CO
|EC_number = 200-933-5
|PubChem = 6425
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 21109330
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 131185
|ChEMBL = 3289669
|SMILES2 = CC(C)(O)C(C)(C)O
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = IVDFJHOHABJVEH-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = C6H14O2
|MolarMass = 118.174 g/mol
|Appearance = White solid
|Density = 0.967 g/cm3
|MeltingPtC = 40 to 43
|BoilingPtC = 171 to 173
}}
|Section7={{Chembox Hazards
|ExternalSDS = [http://physchem.ox.ac.uk/MSDS/PI/pinacol.html External MSDS]
|FlashPtC = 77
|GHSPictograms = {{GHS05}}{{GHS07}}
|GHSSignalWord = Warning
|HPhrases = {{H-phrases|228|315|319|335}}
|PPhrases = {{P-phrases|210|240|241|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|405|501}}
}}
|Section8={{Chembox Related
| OtherFunction_label = compounds
| OtherFunction = Pinacolone
}}
}}
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
Reactions
As a vicinal diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g., by heating with sulfuric acid:{{OrgSynth | author = G. A. Hill and E. W. Flosdorf | title = Pinacolone | prep = CV1P0462 | collvol = 1 | collvolpages = 462 | year = 1941}}
Pinacol can be used with borane and boron trichloride to produce useful synthetic intermediates such as pinacolborane, bis(pinacolato)diboron,{{OrgSynth | collvol = 10 | collvolpages = 115 | year = 2004 | prep = v77p0176 | title = Bis(pinacolato)diboron | author1 = Tatsuo Ishiyama|author2= Miki Murata|author3=Taka-aki Ahiko|author4-link= Norio Miyaura|author4=Norio Miyaura}} and pinacolchloroborane.