1,1′-Bi-2-naphthol

1,1′-Bi-2-naphthol (BINOL) is an organic compound that is often used as a ligand for transition-metal catalysed asymmetric synthesis.

[citation needed] The organic synthesis of BINOL is not a challenge as such but the preparation of the individual enantiomers is.

[5] Aside from the starting materials derived directly from the chiral pool, (R)- and (S)-BINOL in high enantiopurity (>99% enantiomeric excess) are two of the most inexpensive sources of chirality for organic synthesis, costing less than US$0.60 per gram when purchased in bulk from chemical suppliers.

[7] As a consequence, it serves as an important starting material for other sources of chirality for stereoselective synthesis, both stoichiometric and substoichiometric (catalytic).

[8] In a different stoichiometric ratio (1:1 BINOL/LiAlH4 instead of 2:1), the chiral reducing agent BINAL (lithium dihydrido(binaphthoxy)aluminate) is produced.

Skeletal formula of R-BINOL
Skeletal formula of R-BINOL
Skeletal formula of S-BINOL
Skeletal formula of S-BINOL
Ball-and-stick model of R-BINOL
Ball-and-stick model of R-BINOL
Ball-and-stick model of S-BINOL
Ball-and-stick model of S-BINOL
Structure of a chiral phosphoric acid derived from BINOL. [ 6 ]