Chemistry:Benzenediazonium tetrafluoroborate

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Short description: Organic compound containing an –N≡N+ function
Benzenediazonium tetrafluoroborate
PhN2BF4.svg
PhN2BF4.jpg
Names
IUPAC name
Benzenediazonium tetrafluoroborate
Other names
Phenyldiazonium tetrafluoroborate
Identifiers
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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Infobox references
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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.

Synthesis

Diazotization of aniline in the presence of hydrochloric acid:

C6H5NH2 + HNO2 + HCl → [C6H5N2]Cl + 2 H2O

The tetrafluoroborate can be obtained from crude benzenediazonium chloride by salt metathesis using tetrafluoroboric acid.

[C6H5N2]Cl + HBF4 → [C6H5N2]BF4 + HCl

The tetrafluoroborate is more stable than the chloride.[2]

Properties

Main page: Chemistry:Diazonium compound

The diazo group (N2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives:

C6H5N2+ + Nu → C6H5Nu + N2

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]

Safety

Whereas the chloride salt is explosive,[5] the tetrafluoroborate is readily isolated.

References

  1. March, J. (1992). Advanced Organic Chemistry (4th ed.). New York: J. Wiley and Sons. ISBN 0-471-60180-2. 
  2. Flood, D. T. (1933). "Fluorobenzene". Org. Synth. 13: 46. doi:10.15227/orgsyn.013.0046. 
  3. Hartman, W. W.; Dickey, J. B. (1934). "Diazoaminobenzene". Organic Syntheses 14: 24. doi:10.15227/orgsyn.014.0024. 
  4. Cygler, Miroslaw; Przybylska, Maria; Elofson, Richard Macleod (1982). "The Crystal Structure of Benzenediazonium Tetrafluoroborate, C6H5N2+•BF41". Canadian Journal of Chemistry 60 (22): 2852–2855. doi:10.1139/v82-407. 
  5. Nesmajanow, A. N. (1932). "β-Naphthylmercuric chloride". Organic Syntheses 12: 54. http://www.orgsyn.org/demo.aspx?prep=cv2p0432. ; Collective Volume, 2, pp. 432