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595721

Sigma-Aldrich

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

97%

Synonym(s):

(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-1,1-Binaphthol, (R)-Dibromo-BINOL, (R)-Dibromo-bi-2-naphthol

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About This Item

Empirical Formula (Hill Notation):
C20H12Br2O2
CAS Number:
111795-43-8
Molecular Weight:
444.12
MDL number:
MFCD03093629
UNSPSC Code:
12352005
PubChem Substance ID:
24881599
NACRES:
NA.22

Assay

97%

form

solid

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

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

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Highly anti-selective catalytic asymmetric aldol reactions.
Ishitani H, et al.
Journal of the American Chemical Society, 122(22), 5403-5404 (2000)
Asymmetric intramolecular [3+2] cycloaddition reactions of acylhydrazones/olefins using a chiral zirconium catalyst.
Kobayashi S, et al.
Journal of the American Chemical Society, 124(46), 13678-13679 (2002)

Articles

BINOL and Derivatives

We present an article concerning BINOL and Derivatives.

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