Isobutyraldehyde
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| Names | |
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| IUPAC name
2-Methylpropanal
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| Other names
2-Methylpropionaldehyde
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.045 |
PubChem CID
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| RTECS number | NQ4025000 |
| UNII | |
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| 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 |
| -46.38·10−6 cm3/mol | |
Refractive index (nD)
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1.374 |
| Hazards | |
| Main hazards | flammable |
| R-phrases (outdated) | 11 |
| S-phrases (outdated) | 16 |
| Flash point | −19 °C; −2 °F; 254 K |
| Related compounds | |
Related alkyl aldehydes
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Lilial |
Related compounds
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Butyraldehyde Propionaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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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[edit]
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[edit]
Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde.[2]
References[edit]
- ^ 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.
- ^ a b 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; 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.
