Isobutyraldehyde

Isobutyraldehyde
Ball-and-stick model of the isobutyraldehyde molecule
Names
Preferred IUPAC name
2-Methylpropanal
Other names
2-Methylpropionaldehyde
Identifiers
3D model (JSmol)
605330
ChEBI
ChemSpider
ECHA InfoCard 100.001.045 Edit this at Wikidata
EC Number
  • 201-149-6
1658
RTECS number
  • NQ4025000
UNII
UN number 2045
  • InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 checkY
    Key: AMIMRNSIRUDHCM-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O/c1-4(2)3-5/h3-4H,1-2H3
    Key: AMIMRNSIRUDHCM-UHFFFAOYAE
  • CC(C)C=O
Properties
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)
moderate
Solubility in other solvents miscible in organic solvents
-46.38·10−6 cm3/mol
1.374
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H319
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).
checkY verify (what is checkY☒N ?)

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+

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

Other routes

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

  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; 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.

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