Isobutyraldehyde

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Isobutyraldehyde
2-Methyl-2-propanal structural formulae.png
Identifiers
CAS number 78-84-2 YesY
PubChem 6561
ChemSpider 6313 YesY
UNII C42E28168L YesY
ChEBI CHEBI:48943 YesY
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 (−85 °F; 208 K)
Boiling point 63 °C (145 °F; 336 K)
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

Hexyl cinnamaldehyde
2-Methylundecanal

Related compounds Butyraldehyde
Propionaldehyde
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[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]

  1. ^ 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. ^ 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
  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.