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Acetone imine, or 2-propanimine is an
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
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
and an imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...
with the chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
(CH3)2CNH. It is a volatile and flammable
A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...
liquid at room temperature
Colloquially, "room temperature" is a range of air temperatures that most people prefer for indoor settings. It feels comfortable to a person when they are wearing typical indoor clothing. Human comfort can extend beyond this range depending on ...
. 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 fromacetone cyanohydrin
Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a s ...
. Dicyclohexylcarbodiimide (CyN=C=NCy) serves as the scavenger for hydrogen cyanide
Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...
:
:(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
Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s ...
. Upon standing, acetone imine undergoes further condensation to give the tetrahydropyrimidine
Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The othe ...
called acetonin, with loss of ammonia.
The imine of hexafluoroacetone, ((CF3)2C=NH) is by contrast robust..
References
{{reflist Imines