Structure via PubChem · Public domain (PubChem)
BINAP
Sign in to saveAlso known as (±)-BINAP, (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, (+/−)-BINAP
thumb|right|Ball and stick model of BINAP viewed as above
In the Vinony graph
Within Vinony's link graph, BINAP is referenced by 44 other articles, and connects out to enantiomer, stereoselectivity and Organic Syntheses.
It sits within the topics Chembox having GHS data, Chembox image size set and Chemical articles with multiple CAS registry numbers.
Its subject is documented across 18 Wikipedia language editions.
Chemical data
- Formula
- C44H32P2
- Molecular weight
- 622.7 g/mol
- IUPAC name
- [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
- 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
- InChIKey
- MUALRAIOVNYAIW-UHFFFAOYSA-N
- XLogP
- 11.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- 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
Encyclopedic overview
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°.
Excerpted from Wikipedia’s “BINAP” article, available under the CC BY-SA 4.0 licence.