Isobutyraldehyde

Isobutyraldehyde
Ball-and-stick model of the isobutyraldehyde molecule
Names
IUPAC name
2-methylpropanal
Other names
2-Methylpropionaldehyde
Identifiers
78-84-2 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:48943 YesY
ChemSpider 6313 YesY
ECHA InfoCard 100.001.045
PubChem 6561
RTECS number NQ4025000
UNII C42E28168L YesY
Properties
C4H8O
Molar mass 72.11 g/mol
Appearance colourless liquid
Density 0.79 g/cm3
Melting point −65 °C (−85 °F; 208 K)
Boiling point 63 °C (145 °F; 336 K)
moderate
Solubility in other solvents miscible in organic solvents
1.374
Hazards
Main hazards flammable
R-phrases 11
S-phrases 16
Flash point −19 °C; −2 °F; 254 K
Related compounds
Related alkyl aldehydes
Lilial

Hexyl cinnamaldehyde
2-Methylundecanal

Related compounds
Butyraldehyde
Propionaldehyde
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

Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal).[1] Isobutyraldehyde is manufactured, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizaro reaction even though it has alpha hydrogen atom.

Synthesis

Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually. [2]

Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutraldehyde.

It can also be produced using engineered bacteria.[3]

Reactions

Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde.[2]

References

  1. Isobutyraldehyde is a retained trivial name under the IUPAC rules.Panico R, Powell WH, Richer JC, eds. (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds. IUPAC/Blackwell Science. ISBN 0-632-03488-2.
  2. 1 2 Boy Cornils, Richard W. Fischer, Christian Kohlpaintner "Butanals" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_447
  3. Atsumi, Shota; Wendy Higashide; James C. Liao (November 2009). "Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde". Nature Biotechnology. 27 (12): 1177–1180. doi:10.1038/nbt.1586. PMID 19915552.
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