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Mesityl oxide

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Mesityl oxide
Mesityl oxide
Names
Preferred 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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.002 Edit this at Wikidata
EC Number
  • 205-502-5
PubChem CID
RTECS number
  • SB4200000
UNII
UN number 1229
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 Oily, colorless to light-yellow liquid
Odor peppermint- or honey-like
Density 0.858 g/cm
Melting point −53 °C (−63 °F; 220 K)
Boiling point 129.5 °C (265.1 °F; 402.6 K)
Solubility in water 3% (20°C)
Solubility in other solvents Soluble in most organic solvents
Vapor pressure 9 mmHg (20°C)
Refractive index (nD) 1.442
Hazards
Occupational safety and health (OHS/OSH):
Main hazards flammable
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H302, H312, H332
Precautionary statements 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
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)
LC50 (median concentration) 1000 mg/m (rat, 4 hr)
9000 mg/m (rat, 4 hr)
10,000 mg/m (mouse, 2 hr)
2000 mg/m (guinea pig, 7 hr)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 25 ppm (100 mg/m)
REL (Recommended) TWA 10 ppm (40 mg/m)
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 , 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 honey-like odor.

Synthesis

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

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:

Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).

Dimedone is another established use of mesityl oxide.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0385". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Mesityl oxide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Merck Index, 14th Edition
  4. Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses. 1: 53. doi:10.15227/orgsyn.001.0053.
  5. ^ Sifniades, Stylianos; Levy, Alan B. (2000). "Acetone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_079. ISBN 3527306730.

External links

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