Names | |||
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Preferred IUPAC name Propan-2-imine [1] | |||
Other names
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Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
MeSH | Imine Acetone Imine | ||
PubChem CID | |||
CompTox Dashboard (EPA) | |||
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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 | ||
Refractive index (nD) | 1.394 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H319, H336 | |||
P210, P261, P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
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.
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]
The compound hydrolyzes readily:
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]
In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.
In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
In organic chemistry, a ketene is an organic compound of the form RR'C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.
In organic chemistry, an imine 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 bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:
Azo compounds are organic compounds bearing the functional group diazenyl.
In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.
Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.
In organic chemistry, a carbodiimide is a functional group with the formula RN=C=NR. On Earth they are exclusively synthetic, but in interstellar space the parent compound HN=C=NH has been detected by its maser emissions.
Azobisisobutyronitrile (abbreviated AIBN) is an organic compound with the formula [(CH3)2C(CN)]2N2. This white powder is soluble in alcohols and common organic solvents but is insoluble in water. It is often used as a foamer in plastics and rubber and as a radical initiator.
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
The Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively. The oxidant is a combination of dimethyl sulfoxide (DMSO) and dicyclohexylcarbodiimide (DCC). The reaction was first reported by J. Moffatt and his student K. Pfitzner in 1963.
Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol (F
3C)
2C(OH)
2, a geminal diol.
Diphenylketene is a chemical substance of the ketene family. Diphenylketene, like most stable disubstituted ketenes, is a red-orange oil at room temperature and pressure. Due to the successive double bonds in the ketene structure R1R2C=C=O, diphenyl ketene is a heterocumulene. The most important reaction of diphenyl ketene is the [2+2] cycloaddition at C-C, C-N, C-O, and C-S multiple bonds.
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 source of such. For this reason, this cyanohydrin is also highly toxic.
Lithium carbide, Li
2C
2, often known as dilithium acetylide, is a chemical compound of lithium and carbon, an acetylide. It is an intermediate compound produced during radiocarbon dating procedures. Li
2C
2 is one of an extensive range of lithium-carbon compounds which include the lithium-rich Li
4C, Li
6C
2, Li
8C
3, Li
6C
3, Li
4C
3, Li
4C
5, and the graphite intercalation compounds LiC
6, LiC
12, and LiC
18.
Li
2C
2 is the most thermodynamically-stable lithium-rich carbide and the only one that can be obtained directly from the elements. It was first produced by Moissan, in 1896 who reacted coal with lithium carbonate.
Lithium cyanide is an inorganic compound with the chemical formula LiCN. It is a toxic, white coloured, hygroscopic, water-soluble salt that finds only niche uses.
Acetone azine is the simplest ketazine. It is an intermediate in some hydrazine manufacturing processes.
Trifluoroacetone (1,1,1-trifluoroacetone) is an organofluorine compound with the chemical formula CF3C(O)CH3. The compound is a colorless liquid with chloroform-like odour.
Benzophenone imine is an organic compound with the formula of (C6H5)2C=NH. A pale yellow liquid, benzophenone imine is used as a reagent in organic synthesis.