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  • 595721 - (R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol

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595721 Sigma-Aldrich

(R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol

97%

Synonym: (R)-3,3′-Dibromo-1,1′-bi-2-naphthol, (R)-3,3′-Dibromo-[1,1′-Binaphthalene]-2,2′-diol, (R)-Dibromo-1,1′-Bi-2,2′-naphthol, (R)-Dibromo-1,1′-Binaphthalene-2,2′-diol, (R)-Dibromo-BINOL, (R)-Dibromo-1,1-Binaphthol, (R)-Dibromo-bi-2-naphthol

  • CAS Number 111795-43-8

  • Empirical Formula (Hill Notation) C20H12Br2O2

  • Molecular Weight 444.12

  •  MDL number MFCD03093629

  •  PubChem Substance ID 24881599

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
assay   97%
mp   256-260 °C
InChI   1S/C20H12Br2O2/c21-15-9-11-5-1-3-7-13(11)17(19(15)23)18-14-8-4-2-6-12(14)10-16(22)20(18)24/h1-10,23-24H
InChI key   BRTBEAXHUYEXSY-UHFFFAOYSA-N

Description

Application

(R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol reacts with zirconium(IV) tert-butoxide to form a chiral zirconium complex, which can efficiently catalyze:
• anti-selective catalytic asymmetric aldol reactions of silyl enol ethers with aldehydes
• asymmetric intramolecular [3+2] cycloaddition of hydrazone/olefins

Packaging

1 g in glass bottle

250 mg in glass insert

Safety & Documentation

Safety Information

Symbol 
GHS09  GHS09
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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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

Peer-Reviewed Papers
15

References

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