NaOC6H5

NaOC6H5, commonly known as sodium phenoxide or sodium phenolate, is the sodium salt of phenol. Its formula is C6H5ONa. It is an ionic compound consisting of a sodium cation (Na+) paired with the phenoxide anion (C6H5O−). It is typically prepared by neutralizing phenol with sodium hydroxide or by direct reaction of phenol with sodium metal. In solution, the phenoxide ion is stabilized by resonance, with the negative charge delocalized between the oxygen atom and the aromatic ring.

As a nucleophile, sodium phenoxide is a key intermediate in organic synthesis. In Williamson ether synthesis, it reacts with primary alkyl halides or sulfonates to form aryl ethers, such as anisoles. It can also participate in alkylation with other electrophiles under suitable conditions, enabling the preparation of diverse phenyl ether derivatives. The phenoxide ion can also act as a base in deprotonation of other weak acids, and its salts are used as reagents in various synthetic sequences that require an oxygen-centered nucleophile.

Physical properties of sodium phenoxide include its appearance as a solid material that commonly exists as a white crystalline salt. It is typically soluble in water and in polar organic solvents due to its ionic nature, though solubility can vary with formulation and purification.

Safety and handling: sodium phenoxide is caustic and can cause skin and eye irritation. It should be handled with appropriate protective equipment in a well-ventilated area, and stored in a dry, tightly closed container to minimize moisture uptake.