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246948 Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonym: (+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
assay   99%
optical activity   [α]21/D +34°, c = 1 in THF
optical purity   ee: 99% (HPLC)
mp   208-210 °C(lit.)

Description

Packaging

1, 5 g in glass bottle

10 g in poly bottle

Application

A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides.1 Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions.2,3 Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements4 and asymmetric epoxidations.5 The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.6

Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

Price and Availability

Suggested Laboratory Gloves


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(<I>R</I>)-(+)-1,1′-Bi(2-naphthol)

puriss., ≥99.0% (sum of enantiomers, HPLC)

(<I>S</I>)-(−)-1,1′-Bi(2-naphthol)

puriss., ≥99.0% (sum of enantiomers, HPLC)

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
DU3106100

Protocols & Articles

Articles

Indanols

These chiral imine-ligands have recently been used in the vanadium-catalyzed oxidation of sulfides in conjunction with hydrogen peroxide. Optically active sulfoxides are obtained in high yields and e...
Aldrich ChemFiles 2005, 5.4, 7.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, Ligands, Oxidations

Peer-Reviewed Papers

References

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1. J. Org. Chem. 58, 4529, (1993)

2. S. Kobayashi et al. Tetrahedron 50, 11623, (1994)

3. Hattori, K. Yamamoto, H. Synlett, 129, (1993)

4. Maruoka, K. et al. J. Am. Chem. Soc. 117, 1165, (1995)

5. Sasaki, H. et al. Synlett, 300, (1993)

6. Noyori, R. et al. J. Am. Chem. Soc. 106, 6709, 6717, (1984)

New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes. J. Org. Chem. 72, 4424, (2007)

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Merck 14,1226

Fieser 12,190 / Fieser 15,135 / Fieser 16,132 / Fieser 17,116

Aldrich MSDS 1, 189:B / Corp MSDS 1 (1), 414:B / FT-IR 1 (1), 1111:A / FT-IR 2 (2), 1896:D / RegBook 1 (1), 1303:I / Sigma FT-IR 1 (2), 323:A / Structure Index 1, 199:C:2

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