Benzenediazonium chloride

Benzenediazonium chloride is an organic compound with the formula [C6H5N2]Cl. It is a salt of a diazonium cation and chloride. It exists as a colourless solid that is soluble in polar solvents including water. It is the parent member of the aryldiazonium compounds,[1] which are widely used in organic chemistry. Because the salt is unstable, it is not commercially available but is prepared upon demand.

Benzenediazonium chloride

The benzenediazonium ion
Names
IUPAC name
Benzenediazonium chloride
Other names
Phenyldiazonium chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.584
UNII
Properties
C6H5ClN2
Molar mass 140.57 g·mol−1
Appearance colorless crystals
Melting point decomposes
Boiling point decomposes
very good, hydroscopic
Hazards
Main hazards unstable at temperature exceeding 278K (5C), possibly explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

This compound is prepared by diazotization of aniline in the presence of hydrochloric acid:[2] The conversion involves in situ production of nitrous acid (HNO2), which reacts with the aniline:

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

The reactions are conducted at low temperature to minimize decomposition of the diazonium salt. The diazonium salt is not isolated.

Benzenediazonium tetrafluoroborate

Benzenediazonium tetrafluoroborate can be obtained from crude benzenediazonium chloride by salt metathesis using tetrafluoroboric acid. The tetrafluoroborate is more stable.[2]

Properties
Main article: 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]

Safety

The compound is explosive.[4]

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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.CS1 maint: multiple names: authors list (link)
  4. Nesmajanow, A. N. (1932). "β-Naphthylmercuric chloride". Organic Syntheses. 12: 54.; Collective Volume, 2, p. 432
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