Difference between revisions of "Benzonitrile"

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Latest revision as of 21:12, 14 May 2019

Benzonitrile
Names
IUPAC name
Benzonitrile
Preferred IUPAC name
Benzonitrile
Systematic IUPAC name
Benzenecarbonitrile
Other names
Cyanobenzene
Phenyl cyanide
Properties
C7H5N
C6H5CN
Molar mass 103.12 g/mol
Appearance White solid
Odor Almond-like
Density 1.01 g/cm3 (20 °C)
Melting point −13 °C (9 °F; 260 K)
Boiling point 190.7 °C (375.3 °F; 463.8 K)
2 g/100 ml (25 °C)
Solubility Miscible with ethanol
Vvery soluble in acetone, benzene, toluene
Soluble in carbon tetrachloride
Vapor pressure 0.768 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 75 °C (167 °F; 348 K)
Related compounds
Related compounds
Benzyl cyanide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN.

Benzonitrile aka phenyl cyanide is NOT benzyl cyanide.

Properties

Chemical

Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile.

Physical

Benzonitrile is a colorless liquid with a sweet almond odor.

Availability

Delete this section if not applicable

Preparation

Benzonitrile can be prepared by heating a mixture of benzamide and ammonium sulfamate. The reaction produces ammonia and ammonium bisulfate as side products.[1]

Can be prepared by the dehydration of benzamide at high temperatures in the presence of catalyst. Another accessible route is reaction between cuprous cyanide or NaCN with bromobenzene in DMSO, known as Rosenmund–von Braun reaction.

Benzonitrile can be prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at temperatures between 400-450 °C:

C6H5CH3 + 3/2 O2 + NH3 → C6H5(CN) + 3 H2O

Projects

  • Make aromatic compounds
  • Make benzamide

Handling

Safety

Benzonitrile is irritant.

Storage

In closed bottles, away from light and air.

Disposal

Can be neutralized by mixing it with a flammable solvent then incinerated outside or in a fume hood.

References

  1. https://www.nrcresearchpress.com/doi/pdf/10.1139/v56-214

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