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Contents

   



(Top)
  


1 Production  




2 Applications  


2.1  Laboratory uses  






3 History  




4 References  




5 External links  













Benzonitrile






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From Wikipedia, the free encyclopedia
  

Benzonitrile
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name

Benzonitrile

Systematic IUPAC name

Benzenecarbonitrile

Other names

cyanobenzene
phenyl cyanide

Identifiers

CAS Number

3D model (JSmol)
3DMet

Beilstein Reference

 506893
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.596 Edit this at Wikidata
EC Number
  • 202-855-7

Gmelin Reference

 2653
KEGG

PubChem CID
RTECS number
  • DI2450000
UNII
UN number 2224

CompTox Dashboard (EPA)

  • 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

  • N#Cc1ccccc1

Properties

Chemical formula

 C6H5(CN)
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)

Solubility in water

 <0.5 g/100 ml (22 °C)

Magnetic susceptibility (χ)

 -65.19·10−6cm3/mol

Refractive index (nD)

 1.5280
Hazards
GHS labelling:

Pictograms

 GHS07: Exclamation mark

Signal word

 Warning

Hazard statements

 H302, H312

Precautionary statements

 P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P363, P501
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)

Autoignition
temperature

 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 ?)

Infobox references

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.

Production[edit]

It is prepared by ammoxidationoftoluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F).[1]

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

In the laboratory it can be prepared by the dehydration of benzamideorbenzaldehyde oxime[2] or by the Rosenmund–von Braun reaction using cuprous cyanideorNaCN/DMSO and bromobenzene.

Rosenmund-von Braun synthesis

Applications[edit]

Laboratory uses[edit]

Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.[3] It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.[4]

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.[5]

History[edit]

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 hydrogen cyanide (formonitrile). He also coined the name benzonitrile which gave the name to all the group of nitriles.[6]

In 2018, benzonitrile was reported to be detected in the interstellar medium.[7]

References[edit]

  1. ^ Maki, Takao; Takeda, Kazuo (June 2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_555. ISBN 3527306730.
  • ^ Loupy, André; Régnier, Serge (August 1999). "Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes". Tetrahedron Letters. 40 (34): 6221–6224. doi:10.1016/S0040-4039(99)01159-4. ISSN 0040-4039.
  • ^ Cooper, F. C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Organic Syntheses; Collected Volumes, vol. 4, p. 769.
  • ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Organic Syntheses; Collected Volumes, vol. 5, p. 520.
  • ^ Anderson, Gordon K.; Lin, Minren (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Reagents for Transition Metal Complex and Organometallic Syntheses. Inorganic Syntheses. Vol. 28. John Wiley & Sons. pp. 60–63. doi:10.1002/9780470132593.ch13. ISBN 978-0-470-13259-3.
  • ^ Fehling, Hermann (1844). "Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme". Annalen der Chemie und Pharmacie. 49 (1): 91–97. doi:10.1002/jlac.18440490106.
  • ^ McGuire, Brett A.; et al. (January 2018). "Detection of the aromatic molecule benzonitrile (c\sC6H5CN) in the interstellar medium". Science. 359 (6372): 202–205. arXiv:1801.04228. Bibcode:2018Sci...359..202M. doi:10.1126/science.aao4890. PMID 29326270. S2CID 206663501.

    • External links[edit]


    Retrieved from "https://en.wikipedia.org/w/index.php?title=Benzonitrile&oldid=1217329670"
    Categories: 
    ●Aromatic solvents
     ●Phenyl compounds
     ●Benzonitriles
     ●Substances discovered in the 19th century
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     ●Articles containing unverified chemical infoboxes
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