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Mesityl oxide

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Mesityl oxide
Mesityl oxide
Names
IUPAC name 4-methylpent-3-en-2-one
Other names Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.002 Edit this at Wikidata
RTECS number
  • SB4200000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3Key: SHOJXDKTYKFBRD-UHFFFAOYSA-N
  • InChI=1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
SMILES
  • O=C(\C=C(/C)C)C
Properties
Chemical formula C6H10O
Molar mass 98.145 g·mol
Appearance Straw-yellow liquid
Density 0.858 g/cm³
Melting point −53 °C (−63 °F; 220 K)
Boiling point 129.5 °C (265.1 °F; 402.6 K)
Solubility in water Good
Solubility in other solvents Soluble in most organic solvents
Refractive index (nD) 1.442
Hazards
Occupational safety and health (OHS/OSH):
Main hazards flammable
Flash point 87 °F (31 °C)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
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 strong peppermint odor.

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.

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

  1. Merck Index, 11th Edition, 5811
  2. J. B. Conant and Neal Tuttle (1941). "Mesityl oxide". Organic Syntheses; Collected Volumes, vol. 1, p. 345.

External links

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