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- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol
(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol
PRICE INQUIRYCatalog Number
ACM80655818-2
Product Name
(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/80655-81-8.gif)
CAS
80655-81-8
Synonyms
FT-0605159; (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol; (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, 98%; C20H12Br2O2; 6,6'-Dibromo[1,1'-binaphthalene]-2,2'-diol; BC003318; BCP10043; KS-000013V2; BCP10042; (R)-(-)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL;
IUPAC Name
6-bromo-1-(6-bromo-2-hydroxynaphthalen-1-yl)naphthalen-2-ol;
Molecular Weight
444.122g/mol
Molecular Formula
C20H12Br2O2;
Canonical SMILES
C1=CC2=C(C=CC(=C2C3=C(C=CC4=C3C=CC(=C4)Br)O)O)C=C1Br;
InChI
InChI=1S/C20H12Br2O2/c21-13-3-5-15-11(9-13)1-7-17(23)19(15)20-16-6-4-14(22)10-12(16)2-8-18(20)24/h1-10,23-24H;
InChI Key
OORIFUHRGQKYEV-UHFFFAOYSA-N;
Complexity
405
Covalently-Bonded Unit Count
1
Exact Mass
443.918g/mol
H-Bond Acceptor
2
H-Bond Donor
2
Heavy Atom Count
24
Monoisotopic Mass
441.92g/mol
NSC Number
9772
Rotatable Bond Count
1
Topological Polar Surface Area
40.5A^2
Application
(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol is a white to light yellow crystalline compound primarily used in the synthesis of complex organic molecules and chiral ligands. This aromatic chiral Bronsted acid plays a crucial role as a ligand for creating chiral zirconium catalysts, which are essential in facilitating asymmetric Strecker reactions. Additionally, it serves as a ligand in zinc-catalyzed enantioselective Hetero Diels-Alder reactions and is vital for asymmetric Friedel-Crafts reactions involving pyrroles and glyoxylates. Its applications extend to the synthesis of (2R,3S)-3-phenylisoserine hydrochloride and the development of BINOL-derived chiral ligands with aryl substituents at the 6,6-positions, showcasing its versatility in advancing chemical synthesis processes.
April 21, 2025
Exceptional Reagent for Asymmetric Synthesis
We've successfully used the (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol from Alfa Chemistry in our research. It facilitated the efficient synthesis of BINOL-derived chiral ligands and showed excellent performance in asymmetric Strecker reactions.
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