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    Acetone imine

    From Wikipedia - Reading time: 3 min
    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
    CAS Number
    3D model (JSmol)
    ChemSpider
    MeSH Imine Acetone Imine
    PubChem CID
    CompTox Dashboard (EPA)
    InChI
    • InChI=1S/C3H7N/c1-3(2)4/h4H,1-2H3
      Key: XDAGXZXKTKRFMT-UHFFFAOYSA-N
    SMILES
    • CC(=N)C
    Properties
    Chemical formula
    		 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
    Refractive index (nD)
    		 1.394
    Hazards
    GHS labelling:
    Pictograms
    		 GHS02: Flammable GHS07: Exclamation mark
    Signal word
    		 Danger
    Hazard statements
    		 H225, H319, H336
    Precautionary statements
    		 P210, P261, P305+P351+P338
    NFPA 704 (fire diamond)
    NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
    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

    [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 (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..
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