Benzonitrile | |
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Benzonitrile |
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Identifiers | |
CAS number | 100-47-0 |
PubChem | 7505 |
ChemSpider | 7224 |
UNII | 9V9APP5H5S |
KEGG | C09814 |
ChEBI | CHEBI:27991 |
ChEMBL | CHEMBL15819 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C7H5N |
Molar mass | 103.04 g/mol |
Density | 1.0 g/ml |
Melting point |
−13 °C |
Boiling point |
188–191 °C |
Solubility in water | <0.5 g/100 ml (22 °C) |
Refractive index (nD) | 1.5280 |
Hazards | |
EU Index | 608-012-00-3 |
EU classification | Harmful (Xn) |
R-phrases | R21/22 |
S-phrases | (S2), S23 |
NFPA 704 |
2
3
0
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Flash point | 75 °C |
Autoignition temperature |
550 °C |
Explosive limits | 1.4–7.2% |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
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, or by the reaction of sodium cyanide with bromobenzene.
Contents |
Benzonitrile 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 methanolysis.[2]
Benzonitrile can form coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile, e.g. PdCl2(PhCN)2. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.[3]
Benzonitrile was discovered by Hermann Fehling in 1844. He heated ammonium benzoate until it decomposed, and one of the products was benzonitrile. He was able to determine the structure of the product from the already known analogue reaction of ammonium formate yielding hydrocyanic acid. He also coined the name benzonitrile which gave the name to all the group of nitriles.[4]