Acetone imine
Full structural formula of acetone imine with dimensions
Full structural formula of acetone imine with dimensions
Skeletal formula of acetone imine
Skeletal formula of acetone imine
Ball-and-stick model of acetone imine
Ball-and-stick model of acetone imine
Space-filling model of acetone imine
Space-filling model of acetone imine
Names
Preferred IUPAC name
Propan-2-imine[1]
Other names
  • Acetone imine
  • 2-Propanimine
Identifiers
3D model (JSmol)
ChemSpider
MeSH Imine Acetone Imine
  • InChI=1S/C3H7N/c1-3(2)4/h4H,1-2H3
    Key: XDAGXZXKTKRFMT-UHFFFAOYSA-N
  • CC(=N)C
Properties
C3H7N
Molar mass 57.096 g·mol−1
Appearance colorless liquid
Density 0.8 g cm−3 (25 °C)
Boiling point 57–59 °C (135–138 °F; 330–332 K)
log P -0.56
1.394
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H319, H336
P210, P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
3
0
W
Flash point 14.7 °C (58.5 °F; 287.8 K)
Related compounds
Related compounds
 Acetone oxime
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
Upon standing at room temperature, samples of acetone imine degrade to give this heterocycle, called acetonin.

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: 702–704. doi:10.1055/s-1981-29566.
  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..
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