Acetone imine
PinPropan-2-imine[1]
Othernames
  • Acetone imine
  • 2-Propanimine

Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula (CH3)2CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimine. This compound is mainly of academic interest.

Synthesis and reactions

Acetone imine is prepared by dehydrocyanation of the cyanoamine of acetone, which is prepared from acetone cyanohydrin. Dicyclohexylcarbodiimide (CyN=C=NCy) serves as the scavenger for hydrogen cyanide:[2]

(CH3)2C(NH2)CN + CyN=C=NCy → (CH3)2CNH + CyN(H)-C(CN)=NCy

The compound hydrolyzes readily:

(CH3)2CNH + H2O → (CH3)2CO + NH3

This reactivity is characteristic of imines derived from ammonia. Methylene imine (CH2=NH) is also highly reactive, condensing to hexamethylenetetramine. Upon standing, acetone imine undergoes further condensation to give the tetrahydropyrimidine called acetonin, with loss of ammonia.[3]

The imine of hexafluoroacetone, ((CF3)2C=NH) is by contrast robust.[4]

References

  1. ^ "Synonyms". Pubchem
  2. ^ K. Findeisen; H. Heitzer; K. Dehnicke (1981). "Neue Methode zur Herstellung von Aldiminen und Ketiminen". Synthesis. 1981 (9): 702–704. doi:10.1055/s-1981-29566. S2CID 98811861
  3. ^ Matter, E. (1947). "Über ein neues Reaktionsprodukt aus Aceton und Ammoniak (Acetonin) (A new reaction product from acetone and ammonia (acetonine)) I". Helvetica Chimica Acta. 30: 1114–23. doi:10.1002/hlca.19470300503
  4. ^ W. J. Middleton, H. D. Carlson (1970). "Hexafluoroacetone Imine". Org. Syntheses. 50: 81–3. doi:10.15227/orgsyn.050.0081.