Isobutyraldehyde

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Isobutyraldehyde
140px
Ball-and-stick model of the isobutyraldehyde molecule
Names
IUPAC name
2-methylpropanal
Other names
2-Methylpropionaldehyde
Identifiers
78-84-2 YesY
ChEBI CHEBI:48943 YesY
ChemSpider 6313 YesY
Jmol 3D model Interactive image
PubChem 6561
RTECS number NQ4025000
UNII C42E28168L YesY
  • InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 YesY
    Key: AMIMRNSIRUDHCM-UHFFFAOYSA-N YesY
  • 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
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
1.374
Vapor pressure {{{value}}}
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).
YesY verify (what is YesYN ?)
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.Lua error in package.lua at line 80: module 'strict' not found.
  2. 2.0 2.1 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
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