Mesityl oxide

{{chembox

| Watchedfields = changed

| verifiedrevid = 426873209

| Name = Mesityl oxide

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Mesityl oxide.png

| ImageName = Mesityl oxide

| ImageFile1 = Mesityl-oxide-3D-balls.png

| ImageFile2 = Mesityl-oxide-3D-vdW.png

| PIN = 4-Methylpent-3-en-2-one

| OtherNames = Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8526

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SHOJXDKTYKFBRD-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 141-79-7

| PubChem = 8858

| EINECS = 205-502-5

| ChEBI = 89993

| ChEMBL = 3185916

| DTXSID = DTXSID1029170

| UNNumber = 1229

| UNII = 77LAC84669

| SMILES = O=C(\C=C(/C)C)C

| InChI = 1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3

| RTECS = SB4200000

}}

|Section2={{Chembox Properties

| C=6 | H=10 | O=1

| Density = 0.858 g/cm3

| Appearance = Oily, colorless to light-yellow liquid

| Odor = peppermint- or honey-like

| Solubility = 3% (20°C)

| Solvent = other solvents

| SolubleOther = Soluble in most organic solvents

| MeltingPtC = −53

| BoilingPtC = 129.5

| Viscosity =

| RefractIndex = 1.442

| VaporPressure = 9 mmHg (20°C)

}}

|Section3={{Chembox Structure

| Dipole =

}}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards = flammable

| FlashPtF = 87

| FlashPt_ref =

| GHSPictograms = {{GHS02}}{{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|226|302|312|332}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+312|304+340|312|322|330|363|370+378|403+235|501}}

| IDLH = 1400 ppm{{PGCH|0385}}

| LC50 = 1000 mg/m3 (rat, 4 hr)
9000 mg/m3 (rat, 4 hr)
10,000 mg/m3 (mouse, 2 hr)
2000 mg/m3 (guinea pig, 7 hr){{IDLH|141797|Mesityl oxide}}

| LD50 = 1120 mg/kg (rat, oral)
1000 mg/kg (rabbit, oral)
710 mg/kg (mouse, oral)

| REL = TWA 10 ppm (40 mg/m3)

| PEL = TWA 25 ppm (100 mg/m3)

| ExploLimits = 1.4–7.2%

}}

|Section8={{Chembox Related

| OtherCompounds = diacetone alcohol
acetone,
benzylideneacetone

}}

}}

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.Merck Index, 14th Edition

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.{{OrgSynth | last1= Conant|first1=J. B.|last2=Tuttle|first2=N. | doi= 10.15227/orgsyn.001.0053| title = Mesityl Oxide | volume= 1 | page = 53 | year = 1921}}{{cite book|doi=10.1002/14356007.a01_079|chapter=Acetone|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|last1=Sifniades|first1=Stylianos|last2=Levy|first2=Alan B.|isbn=3527306730}}

:400px

Phorone and isophorone may be formed under the same conditions. Isophorone originates via a Michael addition:

:350px

Phorone is formed by continued aldol condensation:

:File:Phoron formation.svg

Uses

Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:

:250px

Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).

Dimedone is another established use of mesityl oxide.

References

{{reflist}}