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595721

Sigma-Aldrich

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

97%

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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
Empirical Formula (Hill Notation):
C20H12Br2O2
CAS Number:
Molecular Weight:
444.12
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
382426246948674737
form

solid

form

-

form

solid

form

solid

mp

256-260 °C

mp

242-244 °C (lit.)

mp

208-210 °C (lit.)

mp

103-145 °C

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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

Regulatory Information

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Customers Also Viewed

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)
Highly anti-selective catalytic asymmetric aldol reactions.
Ishitani H, et al.
Journal of the American Chemical Society, 122(22), 5403-5404 (2000)

Articles

BINOL and Derivatives

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