Sodium phenoxide
| Sodium phenoxide | ||
|---|---|---|
 | ||
| Other names Sodium phenylate | ||
| Identifiers | ||
| CAS number | 139-02-6 | |
| Properties | ||
| Molecular formula | C6H5NaO | |
| Molar mass | 116.09 g/mol | |
| Appearance | White solid | |
| Except where noted otherwise, 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.[1] 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.[2]
Reactions
Sodium phenoxide is a moderately strong base. At low pH's gives phenol:[3]
- PhOH ⇌ PhO− + H+ (K = 10−10)
Sodium phenoxide can be used to prepare phenyl ethers and metal phenolates:[1]
- NaOC6H5 + RBr → ROC6H5 + NaBr
References
- ↑ 1.0 1.1 C. S. Marvel and A. L. Tanenbaum "γ-Phenoxypropyl Bromide" Org. Synth. 1929, vol. 9, pp. 72.
- ↑ Michael Kunert, Eckhard Dinjus, Maria Nauck, Joachim Sieler "Structure and Reactivity of Sodium Phenoxide - Following the Course of the Kolbe-Schmitt Reaction" Chemische Berichte 1997 Volume 130, Issue 10, pages 1461–1465. doi:10.1002/cber.19971301017
- ↑ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 0-471-72091-7
External links
Media related to Sodium phenoxide at Wikimedia Commons