(+/-)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diol, CAS No. 111795-43-8

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111795-43-8

Catalog No. EBD2203434

CAS 111795-43-8

Name (+/-)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diol

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Basic Information

Synonyms: (R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diol (+/-)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diol (R)-(+)-3,3-Dibromo-1,1-bi-2-naphtol (R)-3,3-Dibromo-1,1-bi-2-naphthol (R)-(+)-3,3'-Dibromo-1,1'-bi-2-naphthol 3,3'-dibromo-1,1'-binaphthalene-2,2'-diol (R)-3,3'-Dibromo-1,1'-Bi-2-Naphthol (R)-3,3'-Dibromo-2,2'-Dihydroxy-1,1'-Binaphthyl [1,1'-Binaphthalene]-2,2'-diol,3,3'-dibromo-,(1S)- (s)-3,3 -diol,3,3 -dibromo-,(s)- -binaphthalene-2,2 (S)-(-)-3,3'-Dibromo-1,1'-bi-2-naphthol [1,1'-Binaphthalene]-2,2'-diol,3,3'-dibromo-,(1R)- (r)-3,3 (1r)-3,3 -dibromo[1,1 -dibromo-,(r)-

Molecular Formula: C20H12Br2O2

Molecular Weight: 444.12

MDL Number: MFCD03093629

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

Product Description:

(R)-(+)-3,3'-Dibromo-1,1'-bi-2-naphthol, commonly abbreviated as (R)-(+)-3,3'-Br₂-BINOL, is a chiral organic compound derived from the axially chiral 1,1'-bi-2-naphthol (BINOL) scaffold. It is characterized by the presence of bromine substituents at the 3,3' positions of the naphthyl rings. This modification significantly alters its electronic properties and steric profile compared to the parent BINOL. The primary and most significant application of (R)-(+)-3,3'-Br₂-BINOL is as a precursor or a direct ligand in asymmetric catalysis and materials science. Its electron-withdrawing bromine groups enhance the Lewis acidity of metal centers when coordinated, making it a highly effective chiral ligand for various metal-catalyzed asymmetric reactions, including additions to carbonyl compounds. Furthermore, due to its inherent chirality and extended π-conjugated system, it serves as a crucial building block for constructing chiral functional materials, such as chiral metal-organic frameworks (MOFs), circularly polarized luminescence (CPL) materials, and chiral stationary phases for chromatography. This compound is a valuable tool in both academic research and industrial development for creating enantiomerically pure compounds and advanced chiral materials. It is typically handled under inert atmosphere due to potential sensitivity, and standard safety precautions for organic bromo-compounds should be observed.

Physical Properties

Melting Point: 256-260 °C

Boiling Point: 469.9 °C at 760 mmHg

Flash Point: 238 °C

Density: 1.761 g/cm3

Safety Information

Packing Level: III

Hazard Category: 9

Transport Codes: 3077