Sodium phenoxide

Sodium phenoxide

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Names
Other names Sodium phenolate
Identifiers
CAS Number	139-02-6
ChemSpider	8420
Jmol 3D model	Interactive image
PubChem	4445035
InChI InChI=1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1 Key: NESLWCLHZZISNB-UHFFFAOYSA-M InChI=1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1 Key: NESLWCLHZZISNB-REWHXWOFAP
SMILES c1ccc(cc1)[O-].[Na+]
Properties
Chemical formula	C6H5NaO
Molar mass	116.09 g/mol
Appearance	White solid
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sodium phenoxide is an organic compound with the formula NaOC₆H₅. This white solid is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.

Synthesis and structure

Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide. Anhydrous derivatives can be prepared from phenol and sodium:

Na + HOC₆H₅ → NaOC₆H₅ + 1/2 H₂

Like other sodium alkoxides, crystalline sodium phenolate adopts a complex structures 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 [NaOPh]₄(HMPA)₄.

Ball-and-stick model of the sodium coordination geometry in unsolvated sodium phenoxide Space-filling model of part of a chain in the crystal structure of unsolvated sodium phenoxide

Reactions

Sodium phenoxide is a moderately strong base. At low pH's gives phenol:

PhOH ⇌ PhO⁻ + H⁺          (K = 10⁻¹⁰)

Sodium phenoxide can be used to prepare phenyl ethers and metal phenolates:

NaOC₆H₅ + RBr → ROC₆H₅ + NaBr

External links

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