Methacrolein

Chemical compound

Methacrolein

Names

Preferred IUPAC name

2-Methylprop-2-enal

Other names

Methacrolein
Methacrylaldehyde
Isobutenal

Identifiers

CAS Number

78-85-3^Y

3D model (JSmol)

Interactive image

ChemSpider

6314^Y

ECHA InfoCard

100.001.046

PubChem CID

6562

UNII

9HRB24892H^Y

CompTox Dashboard (EPA)

DTXSID0052540

InChI

InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3^Y
Key: STNJBCKSHOAVAJ-UHFFFAOYSA-N^Y
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).

Y verify (what is ^YN ?)

Infobox references

Chemical compound

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.

References

^ 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.