BINAP
Sign in to saveAlso known as (±)-BINAP, (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, (+/−)-BINAP
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Wikidata facts
- Mass
- 622.197924
Show 4 more facts
- chemical formula
- C₄₄H₃₂P₂
- canonical SMILES
- C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
- melting point
- 283.0
- Commons category
- BINAP
Sources (2)
via Wikidata · CC0
~2 min read
Article
4 sectionsContents
- Use as ligand in asymmetric catalysis
- Preparation
- Further reading
- References
thumb|right|Ball and stick model of BINAP viewed as above
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°.