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.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Bechamp reduction canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T8278434 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Bechamp reduction Context triple: [Zinin reduction, relatedReaction, Bechamp reduction]
-
A.
Corey–Bakshi–Shibata reduction
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
-
B.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
C.
Corey–Kim oxidation
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
-
D.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
E.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Bechamp reduction Target entity description: 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.
-
A.
Corey–Bakshi–Shibata reduction
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
-
B.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
C.
Corey–Kim oxidation
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
-
D.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
E.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
- F. None of above. chosen
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 ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
Instruction
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Input
Subject: Bechamp reduction Description of subject: 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.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.