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631582 Sigma-Aldrich

(R)-(+)-2,2′-Bis(methoxymethoxy)-1,1′-binaphthalene

97%

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
assay   97%
optical activity   [α]20/D +92°, c = 1% in chloroform
mp   101-105 °C (lit.)
SMILES string   COCOc1ccc2ccccc2c1-c3c(OCOC)ccc4ccccc34
InChI   1S/C24H22O4/c1-25-15-27-21-13-11-17-7-3-5-9-19(17)23(21)24-20-10-6-4-8-18(20)12-14-22(24)28-16-26-2/h3-14H,15-16H2,1-2H3
InChI key   YIAQRNNJNMLGTP-UHFFFAOYSA-N

Description

Packaging

250 mg in amber glass bottle

Application

3- or 3,3′-di-substituted products can be obtained easily via ortho-metallation and subsequent treatment with an electrophile to give the corresponding BINOL derivatives.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
Protocols & Articles

Articles

BINOL and Derivatives

BINOL and its derivatives are one of the mostly widely used classes of ligands in asymmetric synthesis; being utilized in a broad array of reactions including: Diels–Alder, carbonyl addition and redu...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 56.
Keywords: Addition reactions, Alkylations, Amidations, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Ligands, Methods, Organic synthesis, Reductions

BINOLs

The structural motif of 1,1’-binaphthyl is considered to be a privileged one for ligands in asymmetric synthesis. These kinds of ligands have shown broad applicability allowing high levels of enantio...
Aldrich ChemFiles 2005, 5.4, 6.
Keywords: Applications, Asymmetric synthesis, Catalysis, Chemfiles, Derivatizations, Desymmetrizations, Ligands, Metallations, Metathesis, Racemizations, Ring-closing metathesis

Peer-Reviewed Papers
15

References

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