Title: BINOL
CAS Registry Number: 602-09-5
CAS Name: [1,1¢-Binaphthalene]-2,2¢-diol
Additional Names: b-binaphthol; 2,2¢-dihydroxy-1,1¢-binaphthyl
Molecular Formula: C20H14O2
Molecular Weight: 286.32
Percent Composition: C 83.90%, H 4.93%, O 11.18%
Literature References: C2-symmetric ligand for metal-mediated stereoselective catalysis. Prepn: H. Walder, Ber. 15, 2166 (1882). Resolution of enantiomers: E. P. Kyba et al., J. Org. Chem. 42, 4173 (1977). Elucidation of catalyst structure: H. Sasai et al., J. Am. Chem. Soc. 115, 10372 (1993). Effect of substituents on enantioselectivity: C. Qian et al., J. Chem. Soc. Perkin Trans. 1 1998, 2097. Photochromism: M. Cavazza et al., J. Am. Chem. Soc. 118, 9990 (1996). Review of role in catalysis: R. Zimmer, J. Suhrbier, J. Prakt. Chem. 339, 758-762 (1997); with titanium: K. Mikami, Pure Appl. Chem. 68, 639-644 (1996); with rare-earth metals: H. Sasai et al., Chemtracts: Org. Chem. 11, 264-267 (1998); of synthesis and use as a chiral reagent and ligand: J. M. Brunel, Chem. Rev. 105, 857-897 (2005).
Properties: Long flat lustrous white needles from alcohol, mp 216-218°.
Melting point: mp 216-218°
Derivative Type: (R)-(+)-Form
CAS Registry Number: 18531-94-7
Properties: Crystals from benzene, mp 207.5-208.5°. [a]54625 +50.9°; [a]58925 +34.3° (c = 1.0 in THF).
Melting point: mp 207.5-208.5°
Optical Rotation: [a]54625 +50.9°; [a]58925 +34.3° (c = 1.0 in THF)
Derivative Type: (S)-(-)-Form
CAS Registry Number: 18531-99-2
Properties: Crystals from benzene, mp 207-208°. [a]54625 -51.3°; [a]58925 -33.3° (c = 1.1 in THF).
Melting point: mp 207-208°
Optical Rotation: [a]54625 -51.3°; [a]58925 -33.3° (c = 1.1 in THF)
Use: Chiral ligand. |