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phenylsodium
Sign in to savePhenylsodium is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.
Chemical data
- Formula
- C6H5Na
- Molecular weight
- 100.09 g/mol
- IUPAC name
- sodium benzene
- SMILES
- C1=CC=[C-]C=C1.[Na+]
- InChIKey
- KSMWLICLECSXMI-UHFFFAOYSA-N
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 100.029
Show 3 more facts
- canonical SMILES
- C1=CC=[C-]C=C1.[Na+]
- chemical formula
- C₆H₅Na
- Commons category
- Phenylsodium
Sources (1)
via Wikidata · CC0
~5 min read
Encyclopedic overview
10 sectionsContents
- Synthesis
- [[Transmetalation]]
- Metal-halogen exchange
- Lithium exchange
- Properties and structure
- Reactions
- Cross-coupling
- Metallation
- See also
- References
Phenylsodium is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.
==Synthesis== The existence of phenylsodium was originally proposed by August Kekulé after observing the formation of sodium benzoate in the reaction of bromobenzene with sodium under carbon dioxide. ===Transmetalation=== In the original synthesis, diphenylmercury and sodium was shown to yield a suspension of phenylsodium:
Excerpted from Wikipedia’s “phenylsodium” article, available under the CC BY-SA 4.0 licence.