Sodium phenoxide (sodium phenolate) is an organic compound with the formula NaOC6H5. It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.
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Preferred IUPAC name
Sodium phenoxide[1] | |
Other names
Sodium phenolate
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3D model (JSmol)
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ECHA InfoCard | 100.004.862 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C6H5NaO | |
Molar mass | 116.09 g/mol |
Appearance | White solid |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Harmful, Corrosive |
Flash point | Non-flammable |
Non-flammable | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide.[2] Anhydrous derivatives can be prepared by combining phenol and sodium. A related, updated procedure uses sodium methoxide instead of sodium hydroxide:[3]
Sodium phenoxide can also be produced by the "alkaline fusion" of benzenesulfonic acid, whereby the sulfonate groups are displaced by hydroxide:
This route once was the principal industrial route to phenol.[citation needed]
Like other sodium alkoxides, solid sodium phenoxide adopts a complex structure involving multiple Na-O bonds. Solvent-free material is polymeric, each Na center being bound to three oxygen ligands as well as the phenyl ring. Adducts of sodium phenoxide are molecular, such as the cubane-type cluster [NaOPh]4(HMPA)4.[4]
Sodium phenoxide is a moderately ?strong ?base. Acidification gives phenol:[5]
The acid-base behavior is complicated by homoassociation, reflecting the association of phenol and phenoxide.[6]
Sodium phenoxide reacts with alkylating agents, such as trimethylene bromide, to afford alkyl phenyl ethers:[2]
The conversion is an extension of the Williamson ether synthesis. With acylating agents, one obtains phenyl esters:[citation needed]
Sodium phenoxide is susceptible to certain types of electrophilic aromatic substitutions. For example, it reacts with carbon dioxide to form 2-hydroxybenzoate, the conjugate base of salicylic acid. In general however, electrophiles irreversibly attack the oxygen center in phenoxide.[citation needed]
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