Acetone imine

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Acetone imine
Full structural formula of acetone imine with dimensions
Skeletal formula of acetone imine
Ball-and-stick 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)
0
3
0
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).

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[edit]

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[edit]

  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..