Isobutyraldehyde

Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal).[1] Isobutyraldehyde is made, 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.

Isobutyraldehyde
Names
IUPAC name
2-Methylpropanal
Other names
2-Methylpropionaldehyde
Identifiers
3D model (JSmol)
605330
ChEBI
ChemSpider
ECHA InfoCard 100.001.045
EC Number
  • 201-149-6
1658
RTECS number
  • NQ4025000
UNII
UN number 2045
Properties
C4H8O
Molar mass 72.11 g/mol
Appearance colourless liquid
Odor Pungent; straw-like
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
-46.38·10−6 cm3/mol
1.374
Hazards
Main hazards flammable
GHS pictograms
GHS Signal word Danger
H225, H319
P210, P233, P240, P241, P242, P243, P264, P280, P303+361+353, P305+351+338, P337+313, P370+378, P403+235, P501
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

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 isobutyraldehyde.

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. 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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