Acetone imine

Acetone imine
Names
Preferred IUPAC name
2-Propanimine
Systematic IUPAC name
Propan-2-imine[1]
Other names
  • acetone imine
Identifiers
ChemSpider
MeSH Imine Acetone Imine
Properties
C3H7N
Molar mass 57.10 g·mol−1
Appearance colorless liquid
Density 0.8 g cm−3 (25 °C)
Melting point −76.32 °C (−105.38 °F; 196.83 K)
Boiling point 71.64 °C (160.95 °F; 344.79 K)[2]
4.083e+005 mg/L
log P -0.56
Vapor pressure 123 kPa (25 °C)[2]
1.394
Hazards
GHS pictograms
GHS signal word DANGER
H225, H319, H336
P210, P261, P305+351+338
NFPA 704
Flammability code 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., gasoline) Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazard W: Reacts with water in an unusual or dangerous manner. E.g., cesium, sodiumNFPA 704 four-colored diamond
3
0
0
Flash point 14.7 °C (58.5 °F; 287.8 K)
Related compounds
Related compounds
 Butanone
Isopropanol
Urea
Carbonic acid
Carbonyl fluoride
Ammonia
Trimethylamine
Acetone
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-propanimide is an organic compound and an imide with the chemical formula (CH3)2CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimide. This compound does not have many uses industrially currently. It is not very soluble in water. When in contact with water, it hydrolyzes to give acetone and ammonia[3].

Synthesis

The method to synthesize acetone imine is similar to the production of acetone oxime. The only difference is that it is made by the condensation of acetone and anhydrous ammonia in the presence of hydrogen chloride.

(CH3)2CO + NH3 → (CH3)2CNH + H2O

Unlike acetone oxime, the acetone imine must be dried because it hydrolyzes when exposed to water[3]

Properties

Acetone imine is a colorless, flammable, volatile, and water reactive liquid in normal conditions. It will ignite readily at temperatures above 14.7 °C (58.5 °F; 287.8K)[2]. When this compound is exposed to moisture, it fumes to give off acetone and ammonia due to hydrolysis[3].

Like acetone oxime, it is not very toxic to humans, however if swallowed, it might be harmful.

References

  1. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/2-Propanimine#section=Synonyms. Missing or empty |title= (help)
  2. 1 2 3 "2-Propanimine - C3H7N - ChemSpider". www.chemspider.com.
  3. 1 2 3 "Hydrolysis of imines to give ketones (or aldehydes) — Master Organic Chemistry". www.masterorganicchemistry.com.
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