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Mesityl oxide

Mesityl oxide
Mesityl oxide
Mesityl-oxide-3D-balls.png
Mesityl-oxide-3D-vdW.png
Names
IUPAC name
4-methylpent-3-en-2-one
Other names
Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
Identifiers
141-79-7 YesY
3D model (Jmol) Interactive image
ChemSpider 8526 YesY
ECHA InfoCard 100.005.002
RTECS number SB4200000
Properties
C6H10O
Molar mass 98.15 g·mol−1
Appearance Oily, colorless to light-yellow liquid
Odor peppermint- or honey-like
Density 0.858 g/cm3
Melting point −53 °C (−63 °F; 220 K)
Boiling point 129.5 °C (265.1 °F; 402.6 K)
3% (20°C)
Solubility in other solvents Soluble in most organic solvents
Vapor pressure 9 mmHg (20°C)
1.442
Hazards
Main hazards flammable
R-phrases R10 R20/21/22
S-phrases S25
Flash point 31 °C; 87 °F; 304 K
Explosive limits 1.4%-7.2%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1120 mg/kg (rat, oral)
1000 mg/kg (rabbit, oral)
710 mg/kg (mouse, oral)
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)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 25 ppm (100 mg/m3)
REL (Recommended)
TWA 10 ppm (40 mg/m3)
IDLH (Immediate danger)
1400 ppm
Related compounds
Related compounds
diacetone alcohol
acetone,
benzylideneacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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 cat urine odor.

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:

Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:


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