(1S)-[1,1'-Binaphthalene]-2,2'-diol

(1S)-[1,1'-Binaphthalene]-2,2'-diol, also known as BINOL, is a chiral organic compound commonly used as a ligand in asymmetric synthesis. It is a white or yellowish powder with a melting point of 205-208°C and a molecular weight of 274.33 g/mol. The compound is soluble in most organic solvents and commonly used in organic synthesis. BINOL is widely used in asymmetric synthesis, particularly in metal-catalyzed asymmetric reactions. Its chiral structure makes it an effective chiral ligand for many transition metal catalysts, including palladium, rhodium, and ruthenium. The ligand can be used in a variety of reactions, including hydrogenation, oxidation, and cross-coupling reactions. BINOL is also used in the synthesis of chiral auxiliaries, which are used to control the stereochemistry of reactions. The chemical structure of BINOL consists of two naphthalene rings connected by a central 2,2'-diol moiety. The chiral center is located at the 1-position of one of the naphthalene rings. The compound is optically active, with the (S)-enantiomer being the most commonly used in asymmetric synthesis. In summary, (1S)-[1,1'-Binaphthalene]-2,2'-diol is a versatile chiral ligand widely used in asymmetric synthesis. Its chemical structure and properties make it an effective tool for controlling the stereochemistry of reactions and synthesizing chiral compounds.