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	141-79-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:89993;
ChEMBL	ChEMBL3185916;
ChemSpider	8526 ;
ECHA InfoCard	100.005.002
EC Number	205-502-5;
PubChem CID	8858;
RTECS number	SB4200000;
UNII	77LAC84669;
UN number	1229
CompTox Dashboard (EPA)	DTXSID1029170;
	InChI 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;
	SMILES O=C(\C=C(/C)C)C;
Properties
Chemical formula	C6H10O
Molar mass	98.145 g·mol−1
Appearance	Oily, colorless to light-yellow liquid[1]
Odor	peppermint- or honey-like[1]
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	3% (20°C)[1]
Solubility in other solvents	Soluble in most organic solvents
Vapor pressure	9 mmHg (20°C)[1]
Refractive index (nD)	1.442
Hazards
Main hazards	flammable
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H302, H312, H332
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P312, P322, P330, P363, P370+378, P403+235, P501
Flash point	31 °C; 87 °F; 304 K [1]
Explosive limits	1.4–7.2%[1]
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1120 mg/kg (rat, oral); 1000 mg/kg (rabbit, oral); 710 mg/kg (mouse, oral)[2]
LC50 (median concentration)	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)[2]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (100 mg/m3)[1]
REL (Recommended)	TWA 10 ppm (40 mg/m3)[1]
IDLH (Immediate danger)	1400 ppm[1]
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).
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	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 honey-like odor.[3]

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[4][5]

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:[5]

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

References

NIOSH Pocket Guide to Chemical Hazards. "#0385". National Institute for Occupational Safety and Health (NIOSH).
"Mesityl oxide". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Merck Index, 14th Edition
Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses. 1: 53. doi:10.15227/orgsyn.001.0053.
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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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0385". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-2] "Mesityl oxide". Immediately Dangerous to Life and 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.

[Ull-5] Sifniades, Stylianos; Levy, Alan B. (2000). "Acetone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_079. ISBN 3527306730.