Bechamp reduction
E723154
Bechamp reduction is an organic redox reaction in which nitro compounds are reduced to amines using iron and acid, historically important in the industrial production of anilines and related aromatic amines.
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
named organic reaction
ⓘ
organic redox reaction ⓘ |
| advantage |
low cost of iron reagent
ⓘ
tolerance of many functional groups ⓘ |
| application |
synthesis of agrochemical intermediates
ⓘ
synthesis of dye intermediates ⓘ synthesis of rubber chemicals ⓘ |
| byproduct |
iron hydroxide
ⓘ
iron oxide ⓘ iron salts ⓘ |
| conditions |
acidic aqueous suspension of iron filings
ⓘ
reflux temperature ⓘ |
| developedBy | Antoine Béchamp NERFINISHED ⓘ |
| eraOfDevelopment | 19th century ⓘ |
| field |
industrial chemistry
ⓘ
organic chemistry ⓘ |
| historicalUse |
dye manufacture
ⓘ
industrial production of aniline ⓘ industrial production of aromatic amines ⓘ pharmaceutical intermediates production ⓘ |
| limitation |
difficult workup on industrial scale
ⓘ
large amounts of inorganic waste ⓘ sludge formation from iron salts ⓘ |
| mechanismFeature |
electron transfer from iron(0) to nitro group
ⓘ
formation of iron(II) and iron(III) salts ⓘ |
| namedAfter | Antoine Béchamp NERFINISHED ⓘ |
| oxidant | nitro group ⓘ |
| product |
amine
ⓘ
aniline ⓘ aromatic amine ⓘ |
| productExample |
o-phenylenediamine
ⓘ
p-phenylenediamine ⓘ |
| reactant |
aromatic nitro compound
ⓘ
nitro compound ⓘ |
| reactionType |
redox reaction
ⓘ
reduction ⓘ |
| reductant | metallic iron ⓘ |
| relatedTo |
catalytic hydrogenation of nitro compounds
ⓘ
zinc–acid reduction of nitro compounds ⓘ |
| selectivity | preferential reduction of nitro group over some other functional groups ⓘ |
| solvent | aqueous medium ⓘ |
| stoichiometryFeature | requires excess iron ⓘ |
| typicalSubstrate |
heteroaromatic nitro compounds
ⓘ
nitrobenzene ⓘ substituted nitrobenzenes ⓘ |
| usesReagent |
acetic acid
ⓘ
acid ⓘ hydrochloric acid ⓘ iron ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.