Isobutyraldehyde

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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

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

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

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

References

  1. ISBN 0-632-03488-2
    .
  2. ^
    doi:10.1002/14356007.a04_447
  3. S2CID 4413113
    .
  4. S2CID 1492698
    .
  5. PMID 23208776
    .
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