141779-46-6

Basic information

• Product Name: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde
• Synonyms: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde;(S)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'- dicarboxaldehyde, 99%e.e.
• CAS NO: 141779-46-6
• Molecular Formula: C₂₂H₁₄O₄
• Molecular Weight: 342.34416
• Mol File: 141779-46-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 499.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.407±0.06 g/cm3(Predicted)
• PKA: 6.27±0.50(Predicted)
• CAS DataBase Reference: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(141779-46-6)
• EPA Substance Registry System: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(141779-46-6)

Safety Data

• Hazardous Substances Data: 141779-46-6(Hazardous Substances Data)

Usage

General Description

S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde, also known as BINOL aldehyde, is a highly important chiral building block in organic chemistry. S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde is primarily used as a chiral ligand in asymmetric synthesis and catalysis. It is widely employed in the development of various enantioselective reactions, including asymmetric hydrogenation, asymmetric allylation, and asymmetric addition reactions. BINOL aldehyde is known for its ability to form stable complexes with transition metal catalysts, allowing for efficient and selective transformations of various substrates. Its unique chiral structure makes it a valuable tool in the production of pharmaceuticals, agrochemicals, and other fine chemicals.

Upstream product

• 121999-12-0 (R)-2,2'-bis(methoxy)-1,1'-binaphthyl-3,3'-dicarbaldehyde 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 68-12-2 N,N-dimethyl-formamide 
• 223389-51-3 2,2’-bis(methoxymethoxy)-[1,1’-binaphthalene]-3,3’-dicarbaldehyde 
• 602-09-5 1,1'-bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 581-71-5 2-Hydroxy-3-naphthaldehyde 
• 30478-88-7 3-bromo-2-naphthol 
• 7260-11-9 phenyl 2-hydroxy-3-naphthoate 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant articles and documents

Copper-Complex-Catalyzed Asymmetric Aerobic Oxidative Cross-Coupling of 2-Naphthols: Enantioselective Synthesis of 3,3′-Substituted C1-Symmetric BINOLs

A novel chiral 1,5-N,N-bidentate ligand based on a spirocyclic pyrrolidine oxazoline backbone was designed and prepared, and it coordinates CuBr in situ to form an unprecedented catalyst that enables efficient oxidative cross-coupling of 2-naphthols. Air serves as an external oxidant and generates a series of C1-symmetric chiral BINOL derivatives with high enantioselectivity (up to 99 % ee) and good yield (up to 87 %). This approach is tolerant of a broader substrates scope, particularly substrates bearing various 3- and 3′-substituents. A preliminary investigation using one of the obtained C1-symmetric BINOL products was used as an organocatalyst, exhibiting better enantioselectivity than the previously reported organocatalyst, for the asymmetric α-alkylation of amino esters.

BINOL derivatives with aggression-induced emission

As fluorescent probes, the small Stokes shift and ACQ effect limit the application of BINOL derivatives. Herein, a new series of BINOL derivatives were synthesized which could be turned from ACQ to AIE fluorophores by changing the electron withdrawing group. Among these compounds, BIN-COP exhibits an obvious AIE property with low cytotoxicity. The bioimaging performance indicated that the designed fluorophores could be successfully used for bioimaging.

ESIPT-based ratiometric probe for Zn2+ detection based on BINOL framework

A ratiometric BINOL-based fluorescent probe for Zn2+ detection was rationally designed and synthesized. Based on the excited-state intramolecular proton transfer (ESIPT) mechanisms, the probe exhibited a significant variation on emission wavele