1226. BINOL

Nomenclature

CAS number: 602-09-5
[1,1′-Binaphthalene]-2,2′-diol; β-binaphthol; 2,2′-dihydroxy-1,1′-binaphthyl.
C20H14O2; mol wt 286.32.
C 83.90%, H 4.93%, O 11.18%.

Description and 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).

Chemical structure

Properties

Long flat lustrous white needles from alcohol, mp 216-218°.

Derivative

(R)-(+)-Form.

Nomenclature

CAS number: 18531-94-7

Properties

Crystals from benzene, mp 207.5-208.5°. [α]54625 +50.9°; [α]58925 +34.3° (c = 1.0 in THF).

Derivative

(S)-(-)-Form.

Nomenclature

CAS number: 18531-99-2

Properties

Crystals from benzene, mp 207-208°. [α]54625 -51.3°; [α]58925 -33.3° (c = 1.1 in THF).

Use

Chiral ligand.