|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||72.11 g/mol|
|Melting point||−65 °C (−85 °F; 208 K)|
|Boiling point||63 °C (145 °F; 336 K)|
|Solubility in other solvents||miscible in organic solvents|
Refractive index (nD)
|GHS Signal word||Danger|
|P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P403+P235, P501|
|Flash point||−19 °C; −2 °F; 254 K|
Related alkyl aldehydes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). 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. It is a colorless volatile liquid.
Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually.
In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. E. coli as well as several other organisms has been genetically modified to produce isobutanol. α-Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol:
- (CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2
- (CH3)2CHCHO + NADH + H+ → (CH3)2CHCH2OH + NAD+
It can also be produced using engineered bacteria.
Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutyraldehyde.
- 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.
- 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
- Atsumi, Shota; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.
- 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.