Mesityl oxide

Mesityl oxide
IUPAC name

4-methylpent-3-en-2-one
Other names

Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
Identifiers
CAS number 141-79-7 Y
ChemSpider 8526 Y
RTECS number SB4200000
Jmol-3D images Image 1
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

  1. ^ Merck Index, 11th Edition, 5811
  2. ^ 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