Acetone imine
{{short description|Chemical compound}}
{{Chembox
| ImageFileL1 = Acetone imine.png
| ImageSizeL1 = 136
| ImageNameL1 = Full structural formula of acetone imine with dimensions
| ImageFileR1 = Acetone imine simple.png
| ImageSizeR1 = 101
| ImageNameR1 = Skeletal formula of acetone imine
| ImageFileL2 = Acetone Imine molecular view.png
| ImageSizeL2 = 131
| ImageNameL2 = Ball-and-stick model of acetone imine
| ImageFileR2 = Acetone Imine Spacefilling.png
| ImageSizeR2 = 106
| ImageNameR2 = Space-filling model of acetone imine
| PIN = Propan-2-imine{{cite web|url =https://pubchem.ncbi.nlm.nih.gov/compound/2-Propanimine#section=Synonyms|title=Synonyms|website=Pubchem}}
| OtherNames = {{plainlist|
- Acetone imine
- 2-Propanimine
}}
|Section1={{Chembox Identifiers
| CASNo = 38697-07-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 142304
| ChemSpiderID = 125534
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| MeSHName = Acetone Imine
| StdInChI=1S/C3H7N/c1-3(2)4/h4H,1-2H3
| StdInChIKey = XDAGXZXKTKRFMT-UHFFFAOYSA-N
| SMILES = CC(=N)C
}}
|Section2={{Chembox Properties
| C=3 | H=7 | N=1
| Appearance = colorless liquid
| Density = 0.8 g cm−3 (25 °C)
| MeltingPtC =
| BoilingPtC = 57-59
| BoilingPt_ref=
| LogP = −0.56
| VaporPressure =
| Solubility =
| RefractIndex = 1.394
}}
|Section5={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| GHSSignalWord = DANGER
| HPhrases = {{H-phrases|225|319|336}}
| PPhrases = {{P-phrases|210|261|305+351+338}}
| NFPA-F = 3
| NFPA-H = 0
| NFPA-R = 0
| NFPA-S = W
| FlashPtC = 14.7
}}
|Section6={{Chembox Related
| OtherCompounds = Acetone oxime
}}
}}
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:{{cite journal|journal=Synthesis|year=1981|pages=702–704| volume=1981| doi=10.1055/s-1981-29566|title=Neue Methode zur Herstellung von Aldiminen und Ketiminen|author1=K. Findeisen |author2=H. Heitzer |author3=K. Dehnicke|issue=9 |s2cid=98811861 }}
:(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.{{cite journal|title=Über ein neues Reaktionsprodukt aus Aceton und Ammoniak (Acetonin) (A new reaction product from acetone and ammonia (acetonine)) I|author=Matter, E.|journal=Helvetica Chimica Acta|year=1947|volume=30|pages=1114–23|doi=10.1002/hlca.19470300503 }}
The imine of hexafluoroacetone, ((CF3)2C=NH) is by contrast robust.{{cite journal| author = W. J. Middleton, H. D. Carlson | title = Hexafluoroacetone Imine | journal= Org. Syntheses | volume = 50| year = 1970| pages=81–3|doi=10.15227/orgsyn.050.0081}}.
References
{{reflist}}