Methacrolein, or methacrylaldehyde, is an unsaturated aldehyde. It is a clear, colorless, flammable liquid.

Methacrolein
Skeletal formula of methacrolein
Skeletal formula of methacrolein
Ball-and-stick model of methacrolein
Ball-and-stick model of methacrolein
Names
Preferred IUPAC name
2-Methylprop-2-enal
Other names
Methacrolein
Methacrylaldehyde
Isobutenal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.046 Edit this at Wikidata
UNII
  • InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3 checkY
    Key: STNJBCKSHOAVAJ-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
    Key: STNJBCKSHOAVAJ-UHFFFAOYAU
  • O=CC(=C)C
Properties
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).
checkY verify (what is checkY☒N ?)

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.

See also

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References

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  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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