1,1'-Bi-2-naphthol

• BINOL
• (RS ) - ( ±)- BINOL
• ( R) - ( )- BINOL
• ( S) - ( -)- BINOL
• Beta -binaphthol
• The chiral binaphthol
• Bis- beta -naphthol
• 2,2 '- Dinaphthol
• 1,1 '-bis -2-naphthol
• 2,2 '- dihydroxydinaphthyl
• Bis- beta -naphthol
• 2,2 '- Dihydroxybinaphthalin

• 602-09-5 [( RS)- BINOL ]
• 18531-94-7 [( R) - ( )- BINOL ]
• 18531-99-2 [( S) - ( -)- BINOL ]

White to beige powder

Fixed

215-218 ° C

Slightly soluble in water

Risk

Template: Infobox chemical / molecular formula search available

1,1 '-bi -2-naphthol ( BINOL ) is an organic substance, the (R) - or (S) -enantiomer is generally used as the auxiliary ligand for the transition metal, or asymmetric synthesis. BINOL has axial chirality ( atropisomers ). The enantiomers can be separated and are stable against racemization. The specific optical rotation of the two enantiomers is ± 33-38 ° (20 ° C, 589 nm) (c = 1, THF). BINOL is a precursor of BINAP, another chiral catalyst.

Production and representation

The separation of the two enantiomers, for example, also by means of the chiral ( 8S, 9R ) - (- ) -N- Benzylcinchonidiniumchlorids effected. In this case ( 70-75 %) can be isolated by its addition and repeated dissolution in ethanol both enantiomers in high yield.

Use

( R) - ( )- BINOL or (S ) - ( -)- BINOL (also derivatives of the pure enantiomers ) is mainly used in asymmetric synthesis.

( R) - ( )- BINOL or (S ) - ( -)- BINOL for example, serves as a ligand a lanthanide in the Shibasaki - aldol reaction to enantioselectively to add unmodified aldehydes to ketones:

From the ( R) - ( )- BINOL or (S ) - ( -)- BINOL derived Heterobimetallkatalysatoren also be used in the enantioselective addition of Phosphornukleophilen to imines.