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Benzonitrile

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Benzonitrile
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Benzonitrile
Systematic IUPAC name
Benzenecarbonitrile
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.596 Edit this at Wikidata
KEGG
RTECS number
  • DI2450000
UNII
  • InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H checkY
    Key: JFDZBHWFFUWGJE-UHFFFAOYSA-N checkY
  • InChI=1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
    Key: JFDZBHWFFUWGJE-UHFFFAOYAY
  • c1ccc(cc1)C#N
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)
-65.19·10−6 cm3/mol
1.5280
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
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).
checkY verify (what is checkY☒N ?)

Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine.

Production

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

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

In the 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 coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is PdCl2(PhCN)2. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.[4]

History

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]

References

  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". Organic Syntheses; Collected Volumes, vol. 4, p. 769.
  3. ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Organic Syntheses; Collected Volumes, vol. 5, p. 520.
  4. ^ Gordon K. Anderson; Minren Lin (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses. Inorganic Syntheses. 28: 60–63. doi:10.1002/9780470132593.ch13. ISBN 978-0-470-13259-3.
  5. ^ Hermann Fehling (1844). "Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme". Annalen der Chemie und Pharmacie. 49 (1): 91–97. doi:10.1002/jlac.18440490106.
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