- Mesityl oxide
-
Mesityl oxide 
4-methylpent-3-en-2-oneOther namesMesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetoneIdentifiers CAS number 141-79-7 
ChemSpider 8526 RTECS number SB4200000 Jmol-3D images Image 1 - O=C(\C=C(/C)C)C
- InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
Key: SHOJXDKTYKFBRD-UHFFFAOYSA-N
InChI=1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
Properties Molecular formula C6H10O Molar mass 98.14 g mol−1 Appearance Straw-yellow liquid Density 0.858 g/cm³ Melting point -53 °C, 220 K, -63 °F
Boiling point 129.5 °C, 403 K, 265 °F
Solubility in water Good Solubility in other solvents Soluble in most organic solvents Refractive index (nD) 1.442 Hazards R-phrases R10 R20/21/22 S-phrases S25 Main hazards flammable Flash point 87 °F (31 °C) Related compounds Related compounds diacetone alcohol
acetone,
benzylideneacetone
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references 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 strong peppermint odor.[1]
Contents
Synthesis
It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[2]
Isophorone may be formed under the same conditions of mesityl oxide production, by a Michael addition. The yields of mesityl oxide and isophorone may vary according to reaction conditions during synthesis:
Uses
Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:
References
- ^ Merck Index, 11th Edition, 5811
- ^ J. B. Conant and Neal Tuttle (1941), "Mesityl oxide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0345; Coll. Vol. 1: 345
External links
Categories:- Ketones
- Alkenes
- Ketone solvents
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