page_title: BINAP
hierarchical_section_title: BINAP
caption_attribution_description: Chemical structure of BINAP. Low energy conformation using MM2 minimization.
context_page_description: BINAP is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions. This C₂-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation. The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle between the naphthyl groups is approximately 90°. The natural bite angle is 93°.
context_section_description: BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound.  This chiral diphosphine ligand is widely used in asymmetric synthesis.  It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions.  This C₂-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings.  The dihedral angle between the naphthyl groups is approximately 90°.  The natural bite angle is 93°.
caption: Ball and stick model of BINAP viewed as above
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