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Organic compound containing an –N≡N+ function From Wikipedia, the free encyclopedia
Benzenediazonium tetrafluoroborate is an organic compound with the formula [C6H5N2]BF4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the aryldiazonium compounds,[1] which are widely used in organic chemistry.
Names | |
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IUPAC name
Benzenediazonium tetrafluoroborate | |
Other names
Phenyldiazonium tetrafluoroborate | |
Identifiers | |
PubChem CID |
|
Properties | |
C6H5BF4N2 | |
Molar mass | 191.92 g·mol−1 |
Appearance | colorless crystals |
Density | 1.565 g/cm3 |
Melting point | decomposes |
Boiling point | decomposes |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diazotization of aniline in the presence of hydrochloric acid:
The tetrafluoroborate can be obtained from crude benzenediazonium chloride by salt metathesis using tetrafluoroboric acid.
The tetrafluoroborate is more stable than the chloride.[2]
The diazo group (N2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives:
These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg-Bachmann reaction. A wide range of groups that can be used to replace N2 including halide, SH−, CO2H−, OH−. Of considerable practical value in the dye industry are the diazo coupling reactions.
The reaction of phenyldiazonium salts with aniline gives 1,3-diphenyltriazene.[3]
The structure of the salt has been verified by X-ray crystallography. The N-N bond distance is 1.083(3) Å.[4]
Whereas the chloride salt is explosive,[5] the tetrafluoroborate is readily isolated.
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