Zinin reduction

E193604

Zinin reduction is an organic chemistry reaction that converts nitro compounds into amines using sulfide-based reducing agents, named after Russian chemist Nikolai Zinin.

All labels observed (1)

Label Occurrences
Zinin reduction canonical 2

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Statements (47)

Predicate Object
instanceOf named reaction in organic chemistry
organic redox reaction
alternativeTo catalytic hydrogenation of nitro compounds
iron–acid reduction of nitro compounds
application laboratory synthesis of aromatic amines
preparation of intermediates for dyes
preparation of intermediates for pharmaceuticals
byproduct elemental sulfur
sulfate or thiosulfate salts
classification heterogeneous organic reaction
sulfur-based reduction
commonReagent ammonium sulfide
hydrogen sulfide in basic solution
polysulfides
sodium sulfide
converts aromatic nitro compounds to aromatic amines
nitroarenes to anilines
nitrobenzene to aniline
discoveredBy Nikolai Zinin NERFINISHED
discoveryCountry Russian Empire
electronSource sulfide ion
field organic chemistry
synthetic organic chemistry
historicalSignificance contributed to the development of the aniline dye industry
one of the earliest methods for preparation of aniline
mechanism involves electron transfer from sulfide to nitro group
proceeds through formation of sulfur-containing intermediates
stepwise reduction of nitro group via nitroso and hydroxylamine intermediates
namedAfter Nikolai Zinin NERFINISHED
product primary aromatic amines
reactionType reduction of nitro compounds
reagentType sulfide-based reducing agents
relatedReaction Bechamp reduction
catalytic hydrogenation of nitroarenes
safetyConsideration generates malodorous sulfur-containing byproducts
uses toxic hydrogen sulfide or sulfide salts
selectivity generally preserves other reducible groups less reactive than nitro under these conditions
selective for nitro group reduction
stoichiometry requires multiple equivalents of sulfide per nitro group reduced
substrate nitrobenzene
other aromatic nitro compounds
substituted nitrobenzenes
typicalConditions basic pH
reflux temperature
typicalMedium alkaline aqueous solution
basic ethanol–water mixtures
usedFor conversion of nitrobenzene to aniline without metal catalysts

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Referenced by (2)

Full triples — surface form annotated when it differs from this entity's canonical label.

Nikolai Zinin hasNotableConcept Zinin reduction
Zinin notableFor Zinin reduction
subject surface form: Nikolai Zinin