121314-69-0

Basic information

• Product Name: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde
• Synonyms: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde
• CAS NO: 121314-69-0
• Molecular Formula: C₂₂H₁₄O₄
• Molecular Weight: 342.34416
• Mol File: 121314-69-0.mol

Chemical Properties

• Melting Point: 285 °C
• 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: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(121314-69-0)
• EPA Substance Registry System: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde(121314-69-0)

Safety Data

• Hazardous Substances Data: 121314-69-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde is used as a chiral ligand in the asymmetric synthesis of pharmaceuticals. Its unique molecular structure and reactivity contribute to the production of enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Agrochemical Industry:
In the agrochemical sector, R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde serves as a chiral ligand for the synthesis of agrochemicals with high selectivity and efficiency. This ensures the production of active ingredients with minimal environmental impact and improved performance in agricultural applications.
Used in Fine Chemicals Production:
R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3,3'-dicarboxaldehyde is utilized as a key intermediate in the synthesis of various fine chemicals. Its specific reactivity and chiral properties enable the creation of high-quality specialty chemicals for use in a range of industries, including fragrances, dyes, and advanced materials.

Upstream product

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

Downstream Products

• 1228578-42-4 C₅₆H₆₆N₄O₄ 
• 121314-74-7 3,3'-Bis-{[(E)-(S)-1-phenyl-ethylimino]-methyl}-[1,1']binaphthalenyl-2,2'-diol 
• 121350-52-5 3,3'-Bis-{[(E)-(1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethylimino]-methyl}-[1,1']binaphthalenyl-2,2'-diol 
• 121314-78-1 3,3'-Bis-{[(E)-(1R,2S)-2-hydroxy-1-methyl-2-phenyl-ethylimino]-methyl}-[1,1']binaphthalenyl-2,2'-diol 
• 121314-79-2 3,3'-Bis-{[(E)-(S)-1-(hydroxy-diphenyl-methyl)-3-methyl-butylimino]-methyl}-[1,1']binaphthalenyl-2,2'-diol 

Relevant articles and documents

BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents

Mild photoactivation of new BINOL-amino acid and -amino ester conjugates (BINOLAMs) yielded alkylating and DNA cross-linking agents with high photoefficiency and superior cytotoxicity. Detection of the transient electrophile, by laser flash photolysis (LFP), suggests that BINOL-quinone methides (QMs) are key intermediates in the process. QMs trapping by water, monitored in a time-dependent product distribution analysis, demonstrated that the phototriggered reactivity of BINOLAMs as bis-alkylating agents is the result of a two-step process involving sequential photogeneration of monoalkylating QMs. Light activation of the BINOL-L-amino esters produced cytotoxic QMs very effective against human tumor LoVo cells with EC50 in the 130-230 nM range. Trimethylpsoralen (PS) is about 4 times less potent than our newly tested compounds. BINOL-L-proline methyl ester showed notable photoselectivity because it displayed cytotoxic effects upon irradiation only and was able to efficiently reach the target DNA inside the cells, where it forms both alkylated and cross-linked species.

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.

Strong Aggregation-Induced CPL Response Promoted by Chiral Emissive Nematic Liquid Crystals (N*-LCs)

In this paper we designed a kind of aggregation-induced emission (AIE) chiral fluorescence emitters (R/S-BINOL-CN enantiomers) in the aggregate state. Chiral emissive nematic liquid crystals (N*-LCs) prepared by doping this kind of AIE-active R/S-BINOL-CN enantiomers into a common achiral nematic liquid crystal (N-LC, E7) can self-assemble as the regularly planar Grandjean texture leading to high luminescence dissymmetry factor (glum) of aggregation-induced circularly polarized luminescence (AI-CPL) signal up to 0.41, which can be attributed to dipolar interactions from polar cyano groups and π–π interactions between binaphthyl moiety of the dopant R/S-BINOL-CN and biphenyl group of the host molecules (E7).

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.

1, 1'-bi-2-naphthol derivative and application thereof as fluorescent dye for aqueous coating

The invention relates to a 1, 1'-bi-2-naphthol derivative and an application thereof as fluorescent dye for aqueous coating, the 1, 1'-bi-2-naphthol derivative is a compound shown in a first formula.The 1, 1'-bi-2-naphthol derivative can be used as fluore

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

Compound boranil based on bi bisnaphthol of the framework and its preparation and use

The invention provides a series of Boranil compounds based on 1,1'-binaphthol parents, a preparation method of the compounds, and application of the compounds on detection of fluorine ions. The compounds meet one of the following general formulas, X is on

Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for aldehyde allylation: unusual additive effect of trimethylsilyl chloride

Chiral dinuclear titanium(IV) complexes have been found to be more effective catalysts for the asymmetric allylation of p-nitrobenzaldehyde than their mononuclear analogues. The addition of trimethylsilyl chloride to the reaction mixture decreases the rate of the background reaction and increases the yield of the reaction catalysed by the dinuclear complex.

ENANTIOSELEKTIVE KATALYSE, 89 AZYKLISCHE UND MAKROZYKLISCHE BINAPHTHYLDERIVATE

A new synthesis of 3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthyl 1 is described.The macrocyclic compound 3 is formed by schiff base condensation of two moles of 1 with two moles of (R,R)-1,2-diamino-1,2-diphenylethane RR-2.Reduction of 3 yields the macrocy