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
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).
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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.

See also

References

  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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