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
| 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 =
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|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = flammable
| FlashPtF = 87
| 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)
| PEL = TWA 25 ppm (100 mg/m3)
}}
|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}}
Phorone and isophorone may be formed under the same conditions. Isophorone originates via a Michael addition:
Phorone is formed by continued aldol condensation:
Uses
Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:
Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).
Dimedone is another established use of mesityl oxide.
References
{{reflist}}
External links
- [http://www.inchem.org/documents/icsc/icsc/eics0814.htm IPCS INCHEM Description]
- [https://www.cdc.gov/niosh/npg/npgd0385.html CDC - NIOSH Pocket Guide to Chemical Hazards]