BENZONITRILE

{{Chembox new|
ImageFile=Benzonitrile.svg|
IUPACName=Benzonitrile|
Other names cyanobenzene
phenyl cyanide
Formula=C7H5N|
MolarMass=103.04 g/mol|
CASNo=100-47-0|
Density=1.0 g/ml|
MeltingPt=−13 °C|
BoilingPt=188–91 °C|
Solubility=<0.5 g/100 ml (22 °C)|
Solvent=Water|
RefractIndex=1.5280|
SMILES=N#Cc1ccccc1|
InChI=1/C7H5N/c8-6-
7-4-2-1-3-5-7/h1-5H|
Section1=
'Benzonitrile' is the chemical compound with the formula C6H5CN, abbreviated PhCN. This aromatic organic compound is colourless, with a sweet almond odour. It is prepared by the dehydration of benzamide and the reaction of sodium cyanide with bromobenzene.

Contents
As a building block in organic chemistry
As a ligand in coordination chemistry
Safety considerations
References
External links

As a building block in organic chemistry


PhCN is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis,[1] It is a precursor to Ph2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by hydrolysis.[1]

As a ligand in coordination chemistry


PhCN forms coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile. e.g. PdCl2(PhCN)2.[3]

Safety considerations


Benzonitrile is an eye and skin irritant.

References


1.
2.
3. Anderson, G. K.; Lin, M. "Bis(benzonitrile)dichloro Complexes of Palladium and Platinum" Inorganic Syntheses, 1990, volume 28, pages 60-63.ISBN 0-471-52619-3

External links



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