Mesityl oxide: Difference between revisions

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	{{chembox		{{chembox

⚫	\| verifiedrevid = ~~402386394~~
			\| Watchedfields = changed
⚫	\| ~~Name~~ = Mesityl oxide
		⚫	\| verifiedrevid = 426873209
⚫	\| ~~ImageFile~~ = Mesityl oxide.png
	\| ~~ImageName~~ = Mesityl oxide		\| Name = Mesityl oxide
			\| ImageFile_Ref = {{chemboximage\|correct\|??}}
⚫	\| ImageFile1 = Mesityl-oxide-3D-balls.png
	\| ~~ImageFile2~~ = Mesityl-oxide~~-3D-vdW~~.png		\| ImageFile = Mesityl oxide.png
		⚫	\| ImageName = Mesityl oxide
⚫	\| ~~IUPACName~~ = 4-~~methylpent~~-3-en-2-one
		⚫	\| ImageFile1 = Mesityl-oxide-3D-balls.png
⚫	\| OtherNames = Mesityl oxide<br />Isobutenyl methyl ketone<br />Methyl isobutenyl ketone<br />Isopropylidene acetone~~'''~~
		⚫	\| ImageFile2 = Mesityl-oxide-3D-vdW.png
⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| PIN = 4-Methylpent-3-en-2-one
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| OtherNames = Mesityl oxide<br />Isobutenyl methyl ketone<br />Methyl isobutenyl ketone<br />Isopropylidene acetone
		⚫	\|Section1={{Chembox Identifiers
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 8526		\| ChemSpiderID = 8526
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
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	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 141-79-7		\| CASNo = 141-79-7
			\| PubChem = 8858
⚫	\| SMILES = O=C(\C=C(/C)C)C
			\| EINECS = 205-502-5
⚫	\| InChI = 1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
	\| ~~RTECS~~ = ~~SB4200000~~		\| ChEBI = 89993
			\| ChEMBL = 3185916
			\| DTXSID = DTXSID1029170
			\| UNNumber = 1229
			\| UNII = 77LAC84669
		⚫	\| SMILES = O=C(\C=C(/C)C)C
		⚫	\| InChI = 1/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
			\| RTECS = SB4200000
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| C=6\|H=10\|O=1		\| C=6 \| H=10 \| O=1
	\| Density = 0.858 g/cm³		\| Density = 0.858 g/cm<sup>3</sup>
	\| Appearance = ~~Straw~~-yellow liquid		\| Appearance = Oily, colorless to light-yellow liquid<ref name=PGCH/>
			\| Odor = peppermint- or honey-like<ref name=PGCH/>
	\| Solubility = Good
			\| Solubility = 3% (20°C)<ref name=PGCH/>
	\| Solvent = other solvents
	\| SolubleOther = Soluble in most organic solvents		\| Solvent = other solvents
			\| SolubleOther = Soluble in most organic solvents
	\| MeltingPtC = ~~-53~~		\| MeltingPtC = −53
	\| BoilingPtC = 129.5		\| BoilingPtC = 129.5
	\| Viscosity =		\| Viscosity =
	\| RefractIndex = 1.442		\| RefractIndex = 1.442
			\| VaporPressure = 9 mmHg (20°C)<ref name=PGCH/>
	}}		}}
	\| Section3 = {{Chembox Structure		\|Section3={{Chembox Structure
	\| Dipole =		\| Dipole =
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| ~~ExternalMSDS~~ =		\| ExternalSDS =
	\| MainHazards = flammable		\| MainHazards = flammable
	\| ~~FlashPt~~ = ~~{{convert\|~~87~~\|F\|C}}~~		\| FlashPtF = 87
			\| FlashPt_ref =<ref name=PGCH/>
	\| RPhrases = {{R10}} {{R20/21/22}}
	\| ~~SPhrases~~ = {{~~S25~~}}		\| GHSPictograms = {{GHS02}}{{GHS07}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|226\|302\|312\|332}}
			\| PPhrases = {{P-phrases\|210\|233\|240\|241\|242\|243\|261\|264\|270\|271\|280\|301+312\|302+352\|303+361+353\|304+312\|304+340\|312\|322\|330\|363\|370+378\|403+235\|501}}
			\| IDLH = 1400 ppm<ref name=PGCH>{{PGCH\|0385}}</ref>
			\| LC50 = 1000 mg/m<sup>3</sup> (rat, 4 hr)<br/>9000 mg/m<sup>3</sup> (rat, 4 hr)<br/>10,000 mg/m<sup>3</sup> (mouse, 2 hr)<br/>2000 mg/m<sup>3</sup> (guinea pig, 7 hr)<ref name=IDLH>{{IDLH\|141797\|Mesityl oxide}}</ref>
			\| LD50 = 1120 mg/kg (rat, oral)<br/>1000 mg/kg (rabbit, oral)<br/>710 mg/kg (mouse, oral)<ref name=IDLH/>
			\| REL = TWA 10 ppm (40 mg/m<sup>3</sup>)<ref name=PGCH/>
			\| PEL = TWA 25 ppm (100 mg/m<sup>3</sup>)<ref name=PGCH/>
			\| ExploLimits = 1.4–7.2%<ref name=PGCH/>
	}}		}}
	\| Section8 = {{Chembox Related		\|Section8={{Chembox Related
	\| ~~OtherCpds~~ = ]<br />],<br />]		\| OtherCompounds = ]<br />],<br />]
	}}		}}
	}}		}}

	'''Mesityl oxide''' is a ] with the formula CH<sub>3</sub>C(O)CH=C(CH<sub>3</sub>)<sub>2</sub>. This compound is a colorless, volatile ] with a ~~strong ]~~ odor.<ref>'']'', ~~11th~~ Edition~~, '''5811'''~~</ref>		'''Mesityl oxide''' is a ] with the formula CH<sub>3</sub>C(O)CH=C(CH<sub>3</sub>)<sub>2</sub>. This compound is a colorless, volatile ] with a honey-like odor.<ref>'']'', 14th Edition</ref>

	==Synthesis==		==Synthesis==
	It is prepared by the ] of ] to give ], which readily dehydrates to give this compound.<ref>{{OrgSynth \| ~~prep~~=~~cv1p0345~~ \| title = Mesityl ~~oxide~~ \| ~~collvol~~ = 1 \| ~~collvolpages~~ = ~~345~~ \| year = ~~1941~~ ~~\| author~~= ] ~~and~~ ~~Neal~~ ~~Tuttle~~}}</ref>		It is prepared by the ] of ] to give ], which readily dehydrates to give this compound.<ref>{{OrgSynth \| last1= Conant\|first1=J. B.\|last2=Tuttle\|first2=N. \| doi= 10.15227/orgsyn.001.0053\| title = Mesityl Oxide \| volume= 1 \| page = 53 \| year = 1921}}</ref><ref name=Ull>{{cite book\|doi=10.1002/14356007.a01_079\|chapter=Acetone\|title=Ullmann's Encyclopedia of Industrial Chemistry\|year=2000\|last1=Sifniades\|first1=Stylianos\|last2=Levy\|first2=Alan B.\|isbn=3527306730}}</ref>

	:]		:]

	] may be formed under the same conditions of ~~mesityl~~ ~~oxide production, by~~ a ]~~. The yields of mesityl oxide and isophorone may vary according to reaction conditions during synthesis~~:		] and ] may be formed under the same conditions. Isophorone originates via a ]:

	:]		:]

			] is formed by continued aldol condensation:

			:]

	==Uses==		==Uses==
	Mesityl oxide is used as a solvent and in the production of ] by ]:		Mesityl oxide is used as a solvent and in the production of ] by ]:<ref name=Ull/>
	:]		:]
			Further hydrogenation gives ] (methyl isobutyl carbinol).

			] is another established use of mesityl oxide.

	==References==		==References==
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	==External links==		==External links==
	*		*
			*

	]		]
	]
	]		]

	]
	]
	]
	]
	]
	]
	]

Latest revision as of 11:37, 26 June 2022

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	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,1-3H3Key: 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 (n_D)	1.442
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	flammable
GHS labelling:
Pictograms
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). Y 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

^ NIOSH Pocket Guide to Chemical Hazards. "#0385". National Institute for Occupational Safety and Health (NIOSH).
^ "Mesityl oxide". Immediately Dangerous to Life or 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

Categories: