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Structure via PubChem · Public domain (PubChem)
furoin
Sign in to saveFuroin or 1,2-di(furan-2-yl)-2-hydroxyethanone is an organic compound with formula C10H8O4. It can be produced from furfural by a benzoin condensation reaction catalyzed by cyanide ions.
Chemical data
- Formula
- C10H8O4
- Molecular weight
- 192.17 g/mol
- IUPAC name
- 1,2-bis(furan-2-yl)-2-hydroxyethanone
- SMILES
- C1=COC(=C1)C(C(=O)C2=CC=CO2)O
- InChIKey
- MIJRFWVFNKQQDK-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 63.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 192.042
Show 3 more facts
- chemical formula
- C₁₀H₈O₄
- melting point
- 138.0
- canonical SMILES
- C1=COC(=C1)C(C(=O)C2=CC=CO2)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Reactions
- Uses
- References
Furoin or 1,2-di(furan-2-yl)-2-hydroxyethanone is an organic compound with formula C10H8O4. It can be produced from furfural by a benzoin condensation reaction catalyzed by cyanide ions.
==Reactions== Furoin synthesis from furfural is also catalyzed by vitamin B1 (thiamine). In 1957, Ronald Breslow proposed that this reaction involves a relatively stable carbene form of thiamine. In the catalytic cycle shown below two molecules of furfural react to give furoin, via a thiazol-2-ylidene catalyst, resulting from loss of one proton at carbon 2 of the thiazolium cation of vitamin B1:
Excerpted from Wikipedia’s “furoin” article, available under the CC BY-SA 4.0 licence.
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