BINAP
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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°.[1]
Quick Facts Names, Identifiers ...
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Preferred IUPAC name
([1,1′-Binaphthalene]-2,2′-diyl)bis(diphenylphosphane) | |
Other names
BINAP | |
Identifiers | |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.114.880 |
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CompTox Dashboard (EPA) |
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Properties | |
C44H32P2 | |
Molar mass | 622.688 g·mol−1 |
Appearance | Colorless solid |
Melting point | 239 to 241 °C (462 to 466 °F; 512 to 514 K) (R) 238–240 °C (S) |
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GHS labelling: | |
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H315, H319, H335, H413 | |
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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