{{Chembox | Watchedfields = changed | verifiedrevid = 427151664 | ImageFileL1 = Pinacolone-2D-skeletal.png | ImageCaptionL1 = Skeletal formula | ImageFileL1_Ref = {{Chemboximage|correct|??}} | ImageSizeL1 = 121 | ImageNameL1 = Skeletal formula of pinacolone | ImageFileR1 = Pinacolone-from-xtal-3D-bs-17.png | ImageCaptionR1 = Ball-and-stick model | PIN = 3,3-Dimethylbutan-2-one | OtherNames = ''t''-Butyl methyl ketone<br /> 1,1,1-Trimethylacetone |Section1={{Chembox Identifiers | CASNo = 75-97-8 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3U1AAG3528 | PubChem = 6416 | ChemSpiderID = 6176 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 200-920-4 | UNNumber = 1224 | MeSHName = Pinacolone | RTECS = EL7700000 | Beilstein = 1209331 | ChEBI = 197349 | SMILES = CC(=O)C(C)(C)C | StdInChI = 1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PJGSXYOJTGTZAV-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C = 6 | H = 12 | O = 1 | Appearance = Colorless liquid | Density = 0.801 g cm<sup>−3</sup> | MeltingPtC = -52<ref>{{cite web | url=http://www.chemspider.com/Chemical-Structure.6176.html?rid=b009474b-a0f1-4132-a843-a9137c137689 | title=Pinacolone &#124; C6H12O &#124; ChemSpider}}</ref> | BoilingPtC = 103 to 106 | MagSus = −69.86·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section3={{Chembox Hazards | ExternalSDS = [https://fscimage.fishersci.com/msds/83026.htm External MSDS] | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|302|315|319|332|335|412}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|273|280|301+312|302+352|303+361+353|304+312|304+340|305+351+338|312|321|330|332+313|337+313|362|370+378|403+233|403+235|405|501}} | NFPA-H = 1 | NFPA-F = 4 | NFPA-R = 0 | FlashPtC = 5 }} }}

'''Pinacolone''' (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid with a slight peppermint or camphor odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an asymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions (hydrogenation, reductive amination, etc.). It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman.<ref>{{cite book |title=Handbook of chemical and biological warfare agents |date=24 August 2007 |publisher=CRC Press |isbn=9780849314346 |edition=2nd}}</ref> It is also a controlled export in Australia Group member states.<ref>{{cite web|title=Export Control List: Chemical Weapons Precursors|url=http://www.australiagroup.net/en/precursors.html|website=Australia Group|publisher=australiagroup.net|access-date=7 April 2017|ref=4}}</ref>

==Preparation== Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol).<ref>{{OrgSynth | author = G. A. Hill and E. W. Flosdorf | title = Pinacolone | prep = CV1P0462 | collvol = 1 | collvolpages = 462 | year = 1941}}</ref>

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Industrially, pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of isoprene and formaldehyde via the Prins reaction. It also is generated by ketonization of pivalic acid and acetic acid or acetone over metal oxide catalysts. 3-Methylbutanal is a starting material for 2,3-dimethyl-2-butene, which in turn is converted to pinacolone. Pinacolone can also be produced from 2-methy-2-butanol when reacted with C5 alcohols.<ref>{{Cite book |last1=Siegel |first1=Hardo |last2=Eggersdorfer |first2=Manfred |title=Ullmann's Encyclopedia of Industrial Chemistry|chapter=Ketones|year=2012|volume=20|series=5|issue=6|doi=10.1002/14356007.a15_077|isbn=9783527306732}}</ref>

==Uses== Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides. Some derivatives include:

*retrosynthetic analysis of vibunazole showed that it was derived from pinacolone.{{OR?|date=July 2025}} *It is also used to prepare pinacidil, as well as naminidil. *Stiripentol *Tribuzone *Pivaloylacetonitrile is used in the synthesis of Doramapimod. *Triadimefon *Diclobutrazole *Paclobutrazol *Valconazole * Diethylstilbestrol pinacolone [18922-13-9].<ref>{{cite journal |last1=Oda |first1=T |last2=Sato |first2=Y |last3=Kodama |first3=M |last4=Kaneko |first4=M |title=Inhibition of DNA topoisomerase I activity by diethylstilbestrol and its analogues. |journal=Biological & Pharmaceutical Bulletin |date=July 1993 |volume=16 |issue=7 |pages=708–10 |pmid=8401407 |doi=10.1248/bpb.16.708|doi-access=free }}</ref> *Some kind of Bisphenol A derivative also {{US patent|4599463}} *Thiofanox

==See also== *Pinacol *Pinacolyl alcohol *Soman

==References== {{Reflist}}

{{Chemical agents}}

Category:Hexanones Category:Tert-butyl compounds Category:Nerve agent precursors