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Balz–Schiemann reaction

Lianyungang Klinechem Co.,Ltd | Updated: Nov 29, 2018

The Schiemann reaction (also called the Balz–Schiemann reaction) is a chemical reaction in which a primary aromatic amine is transformed to an aryl fluoride via a diazonium tetrafluorofluoroborate intermediate.[1][2] Both thermal and photolytic decomposition of the diazonium intermediate proceed through an arene cation, as evidenced by the equal product ratios in both cases.[3] Named after the German chemists Günther Schiemann and Günther Balz, this reaction is the preferred route to fluorobenzene and some related derivatives,[4] including 4-fluorobenzoic acid.[5] 



The reaction is similar to the Sandmeyer reaction, which converts diazonium salts to other aryl halides.[6] Other Counterions have been used in place of tetrafluoroborates, such as hexafluorophosphates (PF6-) and hexafluoroantimonates (SbF6-) with improved yields for some substrates.[7]Large-scale thermal decomposition of the diazonium salts is potentially explosive.


1.     Jump up^ Günther Balz; Günther Schiemann (1927). "Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung". Ber. 5 (60): 1186–1190. doi:10.1002/cber.19270600539.

2.     Jump up^ Roe, A. Org. React. 19495, 193. (Review)

3.     Jump up^ Becker, H. G. O., Isreal, G. J. Prakt. Chem. 1978321, 579-586.

4.     Jump up^ Flood, D. T. (1943). "Fluorobenzene"Organic Syntheses.Collective Volume, 2, p. 295

5.     Jump up^ G. Schiemann; W. Winkelmüller (1943). "p-Fluorobenzoic Acid"Organic Syntheses.Collective Volume, 2, p. 299

6.     Jump up^ Swain, C. G.; Rogers, R. J. (1975). "Mechanism of formation of aryl fluorides from arenediazonium fluoborates". J. Am. Chem. Soc. 97 (4): 799–800. doi:10.1021/ja00837a019.

7.     Jump up^ Furuya, Takeru; Klein, Johannas E. M. N.; Ritter, Tobias (2010). "Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides". Synthesis. 11: 1804–1821 – via Reaxys.


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