Isobutyraldehyde

Isobutyraldehyde

Names
IUPAC name 2-methylpropanal
Other names 2-Methylpropionaldehyde
Identifiers
CAS Number	78-84-2
3D model (Jmol)	Interactive image
ChEBI	CHEBI:48943
ChemSpider	6313
ECHA InfoCard	100.001.045
PubChem	6561
RTECS number	NQ4025000
UNII	C42E28168L
InChI InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 Key: AMIMRNSIRUDHCM-UHFFFAOYSA-N InChI=1/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 Key: AMIMRNSIRUDHCM-UHFFFAOYAE
SMILES CC(C)C=O
Properties
Chemical formula	C4H8O
Molar mass	72.11 g/mol
Appearance	colourless liquid
Density	0.79 g/cm^3
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
Main hazards	flammable
R-phrases	11
S-phrases	16
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

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

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

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.