View source for Bechamp reaction

{{Short description|Chemical reaction}}
{{For|Bechamp reduction of aromatic nitro compounds|Bechamp reduction}}

In [[organic synthesis]] the '''Béchamp reaction''' is used for producing [[arsonic acids]] from activated aromatic substrates. The reaction is an [[electrophilic aromatic substitution]], using [[arsenic acid]] as the electrophile.  The reaction proceeds according to this idealized stoichiometry for the preparation of [[arsanilic acid]]:<ref>{{Ullmann |doi=10.1002/14356007.a03_113.pub2|title=Arsenic and Arsenic Compounds |year=2008 |last1=Grund |first1=Sabina C. |last2=Hanusch |first2=Kunibert |last3=Wolf |first3=Hans Uwe |isbn=978-3527306732 }}</ref>
:{{chem2|C6H5NH2  +  H3AsO4  ->  H2O3AsC6H4NH2  +  H2O}}

==Reaction scope==
The reaction was first reported in 1863 by [[Antoine Béchamp]].<ref>{{cite journal | url=http://gallica.bnf.fr/ark:/12148/bpt6k3013s/f1172.item.r= | title=de l'action de la chaleur sur l'arseniate d'analine et de la formation d'un anilide de l'acide arsenique | author=M. A. Bechamp | journal=[[Compt. Rend.]] | year=1863 | volume=56 | pages=1172–1175}}</ref><ref>{{cite journal|author1=C. S. Hamilton  |author2=J. F. Morgan |name-list-style=amp |doi=10.1002/0471264180.or002.10|journal= [[Organic Reactions]]|year=1944|page=2|title=The Preparation of Aromatic Arsonic and Arsinic Acids by the Bart, Bechamp, and Rosenmund Reactions|isbn=0471264180}}</ref>  It is very analogous to the [[Aromatic sulfonation|sulfonation]] of arenes.

The Béchamp reaction was employed in the [[Nobel Prize]]-winning work on [[organoarsenic compound|organoarsenical]]s by Paul Erlich.<ref>{{cite journal|author1=P. Ehrlich |author2=A. Bertheim |name-list-style=amp |journal=[[Chemische Berichte]]|year=1907|volume=40|page= 3292|doi=10.1002/cber.19070400397|title=Überp-Aminophenylarsinsäure|issue=3|url=https://zenodo.org/record/1426249}}</ref>

In one commercial application,  the Béchamp reaction is reaction is used to produce [[roxarsone]], which exhibits an [[Coccidia|anticoccidial]] action and promotes growth in animals.<ref>{{cite journal|author1=John F. Stolz |author2=Eranda Perera |author3=Brian Kilonzo |author4=Brian Kail |author5=Bryan Crable |author6=Edward Fisher |author7=Mrunalini Ranganathan |author8=Lars Wormer |author9=Partha Basu  |name-list-style=amp |title=Biotransformation of 3-Nitro-4-hydroxybenzene Arsonic Acid (Roxarsone) and Release of Inorganic Arsenic by ''Clostridium'' Species|journal= Environ. Sci. Technol.|year= 2007|volume= 41|issue=3|pages= 818–823|doi= 10.1021/es061802i|pmid= 17328188|bibcode=2007EnST...41..818S}}</ref>

==Further reading==
*{{cite journal|author1=H. P. Brown  |author2=C. S. Hamilton  |name-list-style=amp |journal=[[J. Am. Chem. Soc.]]|year=1934|volume=56|page= 151|doi=10.1021/ja01316a047|title=Naphthalenearsonic Acids. The Application of the Béchamp Reaction to α-Naphthylamine}}

== References==
{{reflist}}
{{reaction-stub}}
{{Organic reactions}}
[[Category:Substitution reactions]]
[[Category:Name reactions]]