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Benzonitrile

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Benzonitrile

Benzonitrile
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Benzonitrile
Other names
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
RTECS number DI2450000
UNII  Y
Properties
C7H5N
Molar mass 103.12 g/mol
Density 1.0 g/ml
Melting point −13 °C (9 °F; 260 K)
Boiling point 188 to 191 °C (370 to 376 °F; 461 to 464 K)
<0.5 g/100 ml (22 °C)
1.5280
Hazards
Harmful (Xn)
R-phrases R21/22
S-phrases (S2), S23
NFPA 704
2
3
0
Flash point 75 °C (167 °F; 348 K)
550 °C (1,022 °F; 823 K)
Explosive limits 1.4–7.2%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Benzonitrile is the organic compound is colourless, with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine.

Contents

  • Production 1
  • Applications 2
    • Laboratory uses 2.1
  • History 3
  • References 4
  • External links 5

Production

It is prepared by ammoxidation of toluene, that is its reaction ammonia and oxygen (or air) at 400 to 450 °C.[1]

C6H5CH3 + 3/2 O2 + NH3 → C6H5CN + 3 H2O

In laboratory it can be prepared by the dehydration of benzamide or by the Rosenmund-von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene.

Rosenmund-von Braun synthesis

Applications

Laboratory uses

Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.[2] It is a precursor to Ph2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis.[3]

Benzonitrile forms

  • International Chemical Safety Card 1103

External links

  1. ^ Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555.
  2. ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine".  
  3. ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine".  
  4. ^ Gordon K. Anderson, Minren Lin (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum".  
  5. ^ Hermann Fehling (1844). "Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme".  

References

Benzonitrile was reported by Hermann Fehling in 1844. He found the compound as a product from the thermal dehydration of ammonium benzoate. He deduced its structure from the already known analogue reaction of ammonium formate yielding formonitrile. He also coined the name benzonitrile which gave the name to all the group of nitriles.[5]

History

[4]

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