Isobutyraldehyde

Isobutyraldehyde
Names
	IUPAC name 2-Methylpropanal
	Other names 2-Methylpropionaldehyde
Identifiers
CAS Number	78-84-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	605330
ChEBI	CHEBI:48943 ;
ChemSpider	6313 ;
ECHA InfoCard	100.001.045
EC Number	201-149-6;
Gmelin Reference	1658
PubChem CID	6561;
RTECS number	NQ4025000;
UNII	C42E28168L ;
UN number	2045
CompTox Dashboard (EPA)	DTXSID9021635 ;
	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
Odor	Pungent; straw-like
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
Magnetic susceptibility (χ)	-46.38·10−6 cm3/mol
Refractive index (nD)	1.374
Hazards
Main hazards	flammable
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H319
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P264, P280, P303+361+353, P305+351+338, P337+313, P370+378, P403+235, P501
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 isobutyraldehyde.

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 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; 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.

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[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.

[Ullmann-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.