Mesityl oxide
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| Names
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| Preferred IUPAC name
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| Other names
Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
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| Identifiers
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| ChEBI
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| ChEMBL
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| ChemSpider
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| ECHA InfoCard
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100.005.002 
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| EC Number
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| RTECS number
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| UNII
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| UN number
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1229
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InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3  YKey: SHOJXDKTYKFBRD-UHFFFAOYSA-N YInChI=1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
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| Properties
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C6H10O
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| Molar mass
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98.145 g·mol−1
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| Appearance
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Oily, colorless to light-yellow liquid[1]
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| Odor
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peppermint- or honey-like[1]
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| Density
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0.858 g/cm3
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| Melting point
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−53 °C (−63 °F; 220 K)
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| Boiling point
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129.5 °C (265.1 °F; 402.6 K)
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3% (20°C)[1]
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| Solubility in other solvents
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Soluble in most organic solvents
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| Vapor pressure
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9 mmHg (20°C)[1]
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1.442
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| Hazards
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| Occupational safety and health (OHS/OSH):
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Main hazards
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flammable
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| GHS labelling:
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Warning
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H226, H302, H312, H332
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P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, P501
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| Flash point
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31 °C; 87 °F; 304 K[1]
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| Explosive limits
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1.4–7.2%[1]
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| Lethal dose or concentration (LD, LC):
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1120 mg/kg (rat, oral)
1000 mg/kg (rabbit, oral)
710 mg/kg (mouse, oral)[2]
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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)[2]
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| NIOSH (US health exposure limits):
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TWA 25 ppm (100 mg/m3)[1]
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TWA 10 ppm (40 mg/m3)[1]
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1400 ppm[1]
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| Related compounds
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Related compounds
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diacetone alcohol
acetone,
benzylideneacetone
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chemical compound
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.[3]
Synthesis
It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[4][5]
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:[5]
Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).
Dimedone is another established use of mesityl oxide.
References
External links
