Pinacolone: Difference between revisions

| 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

|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⁻³

| 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 = -69.86·10⁻⁶ cm³/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 unsymmetrical [[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>

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>

:[[File:800px-Pinacol rearragement.png|580px]]

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|last=Siegel|first=H|author2=Eggersdorfer |title=Ketones|journal=Ullman's Encyclopedia of Industrial Chemistry|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.

*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]]

{{Chemical agents}}

[[Category:Hexanones]]

[[Category:Tert-butyl compounds]]

[[Category:Nerve agent precursors]]