1,8-Bis(dimethylamino)naphthalene

1,8-Bis(dimethylamino)naphthalene (also known as Proton Sponge) is a chemical compound with the formula C14H18N2. It is a derivative of naphthalene, containing two dimethylamino functional groups at the 1 and 8 positions of the naphthalene ring.

Chemical Structure and Properties

1,8-Bis(dimethylamino)naphthalene is a colorless solid that is soluble in common organic solvents. The compound is notable for its basicity; it has a pKa of 12.1 in DMSO, which is significantly higher than that of most amines. This high basicity is attributed to the relief of strain upon protonation and the strong electron-donating ability of the dimethylamino groups.

Synthesis

The synthesis of 1,8-Bis(dimethylamino)naphthalene involves the reaction of 1,8-dibromonaphthalene with dimethylamine. The reaction is typically carried out in a polar aprotic solvent such as DMF or DMSO.

Applications

1,8-Bis(dimethylamino)naphthalene is used as a strong base in organic synthesis. It is also used as a non-nucleophilic base in the synthesis of other compounds. In addition, it has been used as a pH indicator in non-aqueous solvents.

Safety

Like many amines, 1,8-Bis(dimethylamino)naphthalene is a skin and eye irritant. It should be handled with appropriate safety precautions.

See Also

• Naphthalene
• Dimethylamine
• DMSO
• DMF