(S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxal dehyde

Name: (S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxal dehyde
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CAS No. 141779-46-6
Cat. No. CS-0086941
Purity≥98%
MDL No.None

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(S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxal dehyde|CS-0086941

Structure of 141779-46-6

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General Information

CAS No. 141779-46-6
Cat. No. CS-0086941
Purity ≥98%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₁₄O₄
Molecular Weight 342.34
Synonym(s) S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde
SMILES OC1=[C@]([C@]2=C(C=CC=C3)C3=CC(C=O)=C2O)C4=CC=CC=C4C=C1C=O

Description

This chiral bis-aldehyde features two hydroxyl groups flanking a binaphthyl backbone, enabling robust coordination in asymmetric catalysis. The ortho-hydroxy aldehyde motifs deliver enhanced solubility and stability under standard conditions, while the rigid binaphthyl scaffold enforces defined stereochemical control. Ideal for ligand synthesis in transition metal catalysis and molecular recognition applications.

Application

(S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde serves as a chiral ligand scaffold in asymmetric catalysis, enabling enantioselective transformations through its rigid binaphthyl backbone and dual aldehyde functionalities. The ortho-hydroxyl groups enhance metal coordination and solubility, while the aldehyde moieties facilitate imine formation and dynamic combinatorial chemistry applications. Bench-stable and readily functionalized, it supports scalable synthesis of transition-metal complexes for stereoselective C–C and C–X bond formations.

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 : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

TPSA 74.6
LogP 4.6962
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Catalysts and Ligands Ligands Double Alcohol Ligands BINOL Ligands

Material Science Material Building Blocks Covalent Organic Frameworks (COFs) Linkers Linkers (Others)

Material Science Polymer/Macromolecule Reagents Covalent Organic Frameworks (COFs) Linkers Linkers (Others)

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

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(S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxal dehyde

CAS No. 141779-46-6

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