Bechamp reaction

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In organic synthesis, the Bechamp reaction is used for producing arsonic acids from activated aromatic rings such as aniline.[1][2][3][4] It was first described by A. J. Bechamp in 1863. The reaction is an electrophilic aromatic substitution, using arsenic acid as a reactant.

One example of an important arsonic acid is roxarsone. This is 4-hydroxy-3-nitrobenzenearsonic acid. It exhibits an anticoccidial action and promotes growth in animals.[5]

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References[edit]

  1. ^ A. J. Bechamp (1863). Compt. Rend. 56: 1172. 
  2. ^ P. Ehrlich and A. Bertheim, (1907). "Überp-Aminophenylarsinsäure". Chemische Berichte 40 (3): 3292. doi:10.1002/cber.19070400397. 
  3. ^ H. P. Brown and C. S. Hamilton, (1934). "Naphthalenearsonic Acids. The Application of the Béchamp Reaction to α-Naphthylamine". J. Am. Chem. Soc. 56: 151. doi:10.1021/ja01316a047. 
  4. ^ C. S. Hamilton and J. F. Morgan (1944). "The Preparation of Aromatic Arsonic and Arsinic Acids by the Bart, Bechamp, and Rosenmund Reactions". Organic Reactions: 2. doi:10.1002/0471264180.or002.10. ISBN 0471264180. 
  5. ^ John F. Stolz, Eranda Perera, Brian Kilonzo, Brian Kail, Bryan Crable, Edward Fisher, Mrunalini Ranganathan, Lars Wormer, and Partha Basu (2007). "Biotransformation of 3-Nitro-4-hydroxybenzene Arsonic Acid (Roxarsone) and Release of Inorganic Arsenic by Clostridium Species". Environ. Sci. Technol. 41 (3): 818–823. doi:10.1021/es061802i. PMID 17328188.