Synonyms:
(R)-N,N-Dimethyl-1,1-binaphthyldiamine
(r)-n,nμ-dimethyl-2,2μ-diamino-1,1μ-binaphthyl,(r)-n,nμ-dimethyl-1,1μ-binaphthalene-2,2μ-diamine
(1r)-n,n'-dimethyl-[1,1'-binaphthalene]-2,2'-diamine
[1,1'-Binaphthalene]-2,2'-diamine,N2,N2'-dimethyl-,(1R)-
[1,1'-Binaphthalene]-2,2'-diamine,N,N'-dimethyl-,(1R)-(9CI)
[1,1'-Binaphthalene]-2,2'-diamine,N,N'-dimethyl-,(R)-
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine
Molecular Formula:
C22H20N2
Molecular Weight:
312.41
Categories:
Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands
Product Description:
(R)-N,N'-Dimethyl-1,1'-binaphthyl-2,2'-diamine, commonly known as (R)-DM-BINAM, is a chiral diamine derivative of 1,1'-bi-2-naphthol (BINOL). It features a rigid, axially chiral binaphthyl backbone with two dimethylamino substituents at the 2 and 2' positions. This compound is a solid at room temperature and serves as a versatile precursor for constructing chiral ligands and catalysts.
The primary application of (R)-DM-BINAM is in asymmetric synthesis as a privileged chiral scaffold. It is widely used to synthesize a variety of sophisticated chiral ligands, such as phosphoramidites and N-heterocyclic carbene (NHC) precursors. These ligands, when complexed with transition metals like palladium, rhodium, or iridium, are highly effective catalysts for a broad range of enantioselective transformations, including hydrogenations, allylic substitutions, and cross-coupling reactions. Its structural rigidity and tunable electronic properties make it invaluable for achieving high enantioselectivity in the synthesis of pharmaceuticals and fine chemicals.
As a stable and readily modifiable chiral building block, (R)-DM-BINAM is a fundamental tool in the development of new catalytic systems for organic and materials chemistry. It is typically handled under inert atmosphere due to the sensitivity of some derived metal complexes.