Sodium phenoxide: Difference between revisions
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| CASNo = 139-02-6 |
| CASNo = 139-02-6 |
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| PubChem = |
| PubChem = 4445035 |
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| ChemSpiderID = 8420 |
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| SMILES = c1ccc(cc1)[O-].[Na+] |
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| InChI = 1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1 |
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| InChIKey = NESLWCLHZZISNB-REWHXWOFAP |
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| StdInChI = 1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1 |
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| StdInChIKey = NESLWCLHZZISNB-UHFFFAOYSA-M }} |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>5</sub>NaO |
| Formula = C<sub>6</sub>H<sub>5</sub>NaO |
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Revision as of 15:59, 23 September 2015
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| Names | |
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| Other names
Sodium phenylate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| 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 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ a b 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 978-0-471-72091-1
External links
Media related to Sodium phenoxide at Wikimedia Commons