# Pinacolone

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> Markdown URL: https://mediated.wiki/source/Pinacolone.md
> Source: https://en.wikipedia.org/wiki/Pinacolone
> Source revision: 1335479618
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{{Chembox
| Watchedfields = changed
| verifiedrevid = 427151664
| ImageFileL1 = Pinacolone-2D-skeletal.png
| ImageCaptionL1 = [Skeletal formula](/source/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](/source/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](/source/ketone) in [organic chemistry](/source/organic_chemistry). It is a colorless liquid with a slight peppermint or camphor odor. It is a precursor to [triazolylpinacolone](/source/triazolylpinacolone) in the synthesis of the fungicide [triadimefon](/source/triadimefon) and in synthesis of the herbicide [metribuzin](/source/metribuzin). The molecule is an asymmetrical [ketone](/source/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](/source/Chemical_Weapons_Convention), due to being related to [pinacolyl alcohol](/source/pinacolyl_alcohol), which is used in the production of [soman](/source/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](/source/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](/source/pinacol_rearrangement), which occurs by protonation of [pinacol](/source/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>

:580px

Industrially, pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-[dioxane](/source/dioxane), which is the product of isoprene and formaldehyde via the [Prins reaction](/source/Prins_reaction).  It also is generated by [ketonization](/source/ketonization) of [pivalic acid](/source/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](/source/retrosynthetic_analysis) of [vibunazole](/source/vibunazole) showed that it was derived from pinacolone.{{OR?|date=July 2025}}
*It is also used to prepare [pinacidil](/source/pinacidil), as well as [naminidil](/source/naminidil).
*[Stiripentol](/source/Stiripentol)
*[Tribuzone](/source/Tribuzone)
*[Pivaloylacetonitrile](/source/Pivaloylacetonitrile) is used in the synthesis of [Doramapimod](/source/Doramapimod).
*[Triadimefon](/source/Triadimefon)
*[Diclobutrazole](/source/Diclobutrazole)
*[Paclobutrazol](/source/Paclobutrazol)
*[Valconazole](/source/Valconazole)
* [Diethylstilbestrol](/source/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](/source/Bisphenol_A) derivative also {{US patent|4599463}}
*[Thiofanox](/source/Thiofanox)

==See also==
*[Pinacol](/source/Pinacol)
*[Pinacolyl alcohol](/source/Pinacolyl_alcohol)
*[Soman](/source/Soman)

==References==
{{Reflist}}

{{Chemical agents}}

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

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Adapted from the Wikipedia article [Pinacolone](https://en.wikipedia.org/wiki/Pinacolone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pinacolone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.