Isobutyraldehyde

Isobutyraldehyde
Names
	Preferred 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
	Occupational safety and health (OHS/OSH):
Main hazards	flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H319
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P403+P235, 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). verify (what is ?) Infobox references

Isobutyraldehyde is the chemical compound with the formula (CH₃)₂CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal).[1] Isobutyraldehyde is made, 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. It is a colorless volatile liquid.

Synthesis

Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually.[2]

Biological routes

In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. E. coli as well as several other organisms has been genetically modified to produce isobutanol. α-Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol:[3]

(CH₃)₂CHC(O)CO₂H → (CH₃)₂CHCHO + CO₂

(CH₃)₂CHCHO + NADH + H⁺ → (CH₃)₂CHCH₂OH + NAD⁺

Other routes

It can also be produced using engineered bacteria.[4]

Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutyraldehyde.

Reactions

Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde.[2] The latter is a precursor to vitamin B5.[5]

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; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.
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. S2CID 1492698.
Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition. 51 (52): 12975. doi:10.1002/anie.201205886. PMID 23208776.

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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

[:0-3] Atsumi, Shota; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.

[4] 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. S2CID 1492698.

[5] Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition. 51 (52): 12975. doi:10.1002/anie.201205886. PMID 23208776.