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{{short description|Chemical compound}}
{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 402388253
| verifiedrevid = 435632264
| Name = Methacrolein
| Name = Methacrolein
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Methacrolein.png
| ImageFileL1 = Methacrolein.png
| ImageNameL1 = Skeletal formula of methacrolein
| ImageSizeL1 = 120px
| ImageFileR1 = Methacrolein-3D-balls-A.png
| ImageNameL1 = Skeletal formula of methacrolein
| ImageNameR1 = Ball-and-stick model of methacrolein
| ImageFileR1 = Methacrolein-3D-balls-A.png
| PIN = 2-Methylprop-2-enal
| ImageSizeR1 = 120px
| OtherNames = Methacrolein<br />Methacrylaldehyde<br />Isobutenal
| ImageNameR1 = Ball-and-stick model of methacrolein
|Section1={{Chembox Identifiers
| IUPACName = 2-Methylprop-2-enal
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| OtherNames = Methacrolein<br />Methacrylaldehyde<br />Isobutenal
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6314
| ChemSpiderID = 6314
| PubChem = 6562
| PubChem = 6562
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| StdInChIKey = STNJBCKSHOAVAJ-UHFFFAOYSA-N
| StdInChIKey = STNJBCKSHOAVAJ-UHFFFAOYSA-N
| CASNo = 78-85-3
| CASNo = 78-85-3
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES = O=CC(=C)C
| UNII = 9HRB24892H
| SMILES = O=CC(=C)C
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>4</sub>H<sub>6</sub>O
| Formula = C<sub>4</sub>H<sub>6</sub>O
| MolarMass = 70.09 g/mol
| MolarMass = 70.09 g/mol
| Density = 0.8470 g/cm³
| Density = 0.847 g/cm<sup>3</sup>
| MeltingPt = -81 °C
| MeltingPtC = −81
| BoilingPt = 69 °C
| BoilingPtC = 69
}}
}}
| Section3 = {{Chembox Related
|Section3={{Chembox Related
| Function = alkenals
| OtherFunction_label = alkenals
| OtherFunctn = [[Citral]]<br />
| OtherFunction = [[Citral]]<br />
[[Citronellal]]<br />
[[Citronellal]]<br />
[[trans-2-Methyl-2-butenal|''trans''-2-Methyl-2-butenal]]
[[trans-2-Methyl-2-butenal|''trans''-2-Methyl-but-2-enal]]
}}
}}
}}
}}


'''Methacrolein''', or methacrylaldehyde, is an [[saturation (chemistry)|unsaturated]] [[aldehyde]]. It is a clear, colorless, flammable liquid that is present in cigarettes when smoking.<ref>{{cite web | title=The risks of passive smoking | url=http://books.google.com/books?id=QZcOAAAAQAAJ&pg=PA23&lpg=PA23&source=bl&ots=GBx_oT-Kaj&sig=lYwIEipofbvcxbNebf52pYp125A&hl=en&ei=FtcASr6TCqXYswP3-5H7BQ&sa=X&oi=book_result&ct=result&resnum=2 | work=Google Books Search | author=Roy J. Shephard | date=1982 | accessdate=2009-05-06}}</ref>
'''Methacrolein''', or methacrylaldehyde, is an [[Saturated and unsaturated compounds|unsaturated]] [[aldehyde]]. It is a clear, colorless, flammable liquid.

Methacrolein is one of two major products resulting from the reaction of [[isoprene]] with OH in the atmosphere, the other product being [[methyl vinyl ketone]] (MVK, also known as butenone).<ref>{{cite journal | doi = 10.1029/92JD02382 | title = Isoprene and its oxidation products, methyl vinyl ketone and methacrolein, in the rural troposphere | journal = Journal of Geophysical Research: Atmospheres | volume = 98 | issue = D1 | pages = 1101–1111 | year = 1993 | last1 = Montzka | first1 = S. A. | last2 = Trainer | first2 = M. | last3 = Goldan | first3 = P. D. | last4 = Kuster | first4 = W. C. | last5 = Fehsenfeld | first5 = F. C. | bibcode = 1993JGR....98.1101M | url = https://zenodo.org/record/1231331}}</ref> These compounds are important components of the atmospheric oxidation chemistry of biogenic chemicals, which can result in the formation of ozone and/or particulates. Methacrylaldehyde is also present in cigarette smoke.<ref>{{cite book | title=The risks of passive smoking| url=https://books.google.com/books?id=QZcOAAAAQAAJ&pg=PA23 | author=Roy J. Shephard | date=1982 | access-date=2009-05-06| isbn=978-0-7099-2334-3}}</ref> It can be found in the [[essential oil]] of the plant [[Big Sagebrush]] (''Artemisia tridentata'') which contains 5% methacrolein.<ref>{{cite book|author=Shakhnoza, Azimova S.|title=Lipids, Lipophilic Components and Essential Oils from Plant Sources|publisher=Springer|year=2012|isbn=978-0-85729-323-7|page=844|url=https://books.google.com/books?id=w74gD4-YxaQC&pg=PT844|display-authors=etal}}</ref>


Industrially, the primary use of methacrolein is in the manufacture of [[polymer]]s and synthetic [[resin]]s.
Industrially, the primary use of methacrolein is in the manufacture of [[polymer]]s and synthetic [[resin]]s.
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==External links==
==External links==
* [http://www.nj.gov/health/eoh/rtkweb/1198.pdf Hazardous Substance Fact Sheet]
* [https://web.archive.org/web/20061012121459/http://www.nj.gov/health/eoh/rtkweb/1198.pdf Hazardous Substance Fact Sheet]


{{Authority control}}
[[Category:Aldehydes]]
[[Category:Alkenes]]
[[Category:Alkenals]]
[[Category:Monomers]]
[[Category:Monomers]]
[[Category:Enones]]


{{organic-compound-stub}}

[[de:Methacrolein]]
[[fr:Méthylpropénal]]
[[nl:Methacroleïne]]
[[fi:Metakryylialdehydi]]
[[sv:Metakrolein]]