Methacrolein

Methacrolein
Skeletal formula of methacrolein	Ball-and-stick model of methacrolein
Names
	Preferred IUPAC name 2-Methylprop-2-enal
	Other names Methacrolein; Methacrylaldehyde; Isobutenal
Identifiers
CAS Number	78-85-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	6314 ;
ECHA InfoCard	100.001.046
PubChem CID	6562;
UNII	9HRB24892H ;
CompTox Dashboard (EPA)	DTXSID0052540 ;
	InChI InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3 Key: STNJBCKSHOAVAJ-UHFFFAOYSA-N ; InChI=1/C4H6O/c1-4(2)3-5/h3H,1H2,2H3 Key: STNJBCKSHOAVAJ-UHFFFAOYAU;
	SMILES O=CC(=C)C;
Properties
Chemical formula	C4H6O
Molar mass	70.09 g/mol
Density	0.847 g/cm3
Melting point	−81 °C (−114 °F; 192 K)
Boiling point	69 °C (156 °F; 342 K)
Related compounds
Related alkenals	Citral; Citronellal; trans-2-Methyl-but-2-enal
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Methacrolein, or methacrylaldehyde, is an 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).^[1] 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.^[2] It can be found in the essential oil of the plant Big Sagebrush (Artemisia tridentata) which contains 5% methacrolein.^[3]

Industrially, the primary use of methacrolein is in the manufacture of polymers and synthetic resins.

Exposure to methacrolein is highly irritating to the eyes, nose, throat and lungs.

^ Montzka, S. A.; Trainer, M.; Goldan, P. D.; Kuster, W. C.; Fehsenfeld, F. C. (1993). "Isoprene and its oxidation products, methyl vinyl ketone and methacrolein, in the rural troposphere". Journal of Geophysical Research: Atmospheres. 98 (D1): 1101–1111. Bibcode:1993JGR....98.1101M. doi:10.1029/92JD02382.
^ Roy J. Shephard (1982). The risks of passive smoking. ISBN 978-0-7099-2334-3. Retrieved 2009-05-06.
^ Shakhnoza, Azimova S.; et al. (2012). Lipids, Lipophilic Components and Essential Oils from Plant Sources. Springer. p. 844. ISBN 978-0-85729-323-7.

[1] Montzka, S. A.; Trainer, M.; Goldan, P. D.; Kuster, W. C.; Fehsenfeld, F. C. (1993). "Isoprene and its oxidation products, methyl vinyl ketone and methacrolein, in the rural troposphere". Journal of Geophysical Research: Atmospheres. 98 (D1): 1101–1111. Bibcode:1993JGR....98.1101M. doi:10.1029/92JD02382.

[2] Roy J. Shephard (1982). The risks of passive smoking. ISBN 978-0-7099-2334-3. Retrieved 2009-05-06.

[3] Shakhnoza, Azimova S.; et al. (2012). Lipids, Lipophilic Components and Essential Oils from Plant Sources. Springer. p. 844. ISBN 978-0-85729-323-7.

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