(S)-[1,1'-Binaphthalene]-2,2'-diamine

Name: (S)-[1,1'-Binaphthalene]-2,2'-diamine
Brand: ChemScene
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CAS No. 18531-95-8
Cat. No. CS-0022860
Purity≥97%
MDL No.None

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(S)-[1,1'-Binaphthalene]-2,2'-diamine|CS-0022860

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Description

(S)-(-)-1,1-Binaphthyl-2,2-diamine may be used in the synthesis of (S)-(+)-N,N-dimethyl-N,N-bis{3-[bis-(1-methyl-2-benzimidazolyl methyl)]-amino]-propyl}-1,1-binaphthyl-2,2-diamine, an octadentate ligand that can form dinuclear and trinuclear copper(II) complexes. It may also be used in the synthesis of (Sa)-N-[2-amino-(1,1-binaphthyl)-2-yl]-4-methylbenzenesulfonamide.

Application

(S)-[1,1'-Binaphthalene]-2,2'-diamine serves as a chiral scaffold for asymmetric catalysis, enabling enantioselective transformations via well-established coordination modes. Its rigid binaphthyl backbone provides defined stereochemistry and facilitates efficient metal complexation, particularly in palladium- and copper-catalyzed reactions. The diamine functionality offers robust functional group tolerance and compatibility with standard synthetic workflows, supporting scalable synthesis of chiral intermediates. Bench-stable and readily purified, it functions as a reliable ligand in cross-coupling and cycloaddition protocols.

General Information

CAS No. 18531-95-8
Cat. No. CS-0022860
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₆N₂
Molecular Weight 284.35
Synonym(s) S-(-)-2,2-Diamino-1,1-binaphthyl
SMILES NC1=[C@]([C@]2=C(C=CC=C3)C3=CC=C2N)C4=CC=CC=C4C=C1

Computational Chemistry Data

TPSA 52.04
LogP 4.8244
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Catalysts and Ligands Ligands Diamine Ligands BINAM Ligands

Catalysis Asymmetric Synthesis Chiral Catalysts, Chiral Ligands, Chiral Reagents Privileged Ligands and Complexes

Catalysis Nitrogen-Donor Ligands Amine Ligands

Key Words

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(S)-[1,1'-Binaphthalene]-2,2'-diamine

CAS No. 18531-95-8

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