Isobutyraldehyde
| Isobutyraldehyde | |
|---|---|
 | |
| IUPAC name 2-methylpropanal | |
| Other names 2-Methylpropionaldehyde | |
| Identifiers | |
| CAS number | 78-84-2  |
| PubChem | 6561 |
| ChemSpider | 6313 |
| UNII | C42E28168L |
| ChEBI | CHEBI:48943 |
| RTECS number | NQ4025000 |
| Jmol-3D images | Image 1 |
| |
| |
| Properties | |
| Molecular formula | C4H8O |
| Molar mass | 72.11 g/mol |
| Appearance | colourless liquid |
| Density | 0.79 g/cm3 |
| Melting point | −65 °C |
| Boiling point | 63 °C |
| Solubility in water | moderate |
| Solubility in other solvents | miscible in organic solvents |
| Refractive index (nD) | 1.374 |
| Hazards | |
| R-phrases | 11 |
| S-phrases | 16 |
| Main hazards | flammable |
| Flash point | −19 °C; −2 °F; 254 K |
| Related compounds | |
| Related alkyl aldehydes | Lilial |
| Related compounds | Butyraldehyde Propionaldehyde |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| 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.
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
- ↑ Isobutyraldehyde is a retained trivial name under the IUPAC rules.Panico, R.; Powell, W. H.; Richer, J. C., eds. (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds. IUPAC/Blackwell Science. ISBN 0-632-03488-2.
- ↑ 2.0 2.1 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: 1177–1180.