345659-34-9

Basic information

• Product Name: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde
• Synonyms: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde
• CAS NO: 345659-34-9
• Molecular Formula: C₂₁H₁₄O₃
• Molecular Weight: 314.33406
• Mol File: 345659-34-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(345659-34-9)
• EPA Substance Registry System: S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(345659-34-9)

Safety Data

• Hazardous Substances Data: 345659-34-9(Hazardous Substances Data)

Usage

Description

S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde, commonly known as BINOL, is a chiral biaryl compound that features two naphthalene rings connected by a carbon-carbon single bond. It is characterized by the presence of two hydroxyl groups and an aldehyde group at the 2, 2', and 3 positions, respectively. BINOL serves as a versatile and valuable building block in asymmetric synthesis, particularly for the creation of chiral ligands in transition metal-catalyzed reactions. Its unique structure allows it to provide stereochemical control in various organic transformations, making it an essential tool in the production of pharmaceuticals, agrochemicals, and fine chemicals. Furthermore, BINOL and its derivatives have been explored for their potential applications in materials science, including the development of liquid crystals and optoelectronic devices.

Uses

Used in Pharmaceutical Industry:
S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is used as a chiral building block for the synthesis of pharmaceuticals, enabling the creation of enantiomerically pure compounds that are essential for the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical industry, S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is utilized as a chiral intermediate for the production of agrochemicals, ensuring the synthesis of enantiomerically pure active ingredients that are crucial for the effectiveness and selectivity of these products.
Used in Fine Chemicals Industry:
S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is employed as a chiral catalyst or ligand in the synthesis of fine chemicals, facilitating asymmetric reactions that lead to the production of enantiomerically pure compounds with specific properties and applications.
Used in Materials Science:
In the field of materials science, S-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is used as a key component in the development of advanced materials such as liquid crystals and optoelectronic devices, leveraging its unique structure to impart specific optical, electronic, and self-assembling properties to these materials.

Upstream product

• 55442-32-5 3,3'-hydroxylmethyl-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 349149-07-1 (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde 

Relevant articles and documents

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

A simple complex: ‘on–off–on’ colorimetric and ratiometric fluorescence response towards fluoride ions and its solid state optical properties

A simple 1,1′-bi-2-naphthol (1,1′-BINOL) boron complex has been rationally designed and synthesized, the structure of which was confirmed by single crystal X-ray diffraction analysis. Furthermore, the complex exhibited turn-on fluorescence for fluoride ions with high selectivity and sensitivity. The recognition mechanism for promoting was determined by 1H, 19F and 11B NMR titrations, which indicated that both the photo-induced electron-transfer (PET) and the intramolecular charge transfer (ICT) effects were functionalized. In addition, the complex showed strong solid-state fluorescence, and the emission spectrum and quantum efficiency (ΦF) of the solid powders were also measured.

BINAPHTHOL ALDEHYDE DERIVATIVES AND METHOD FOR PREPARING THE SAME

The present invention relates to a binaphthol aldehyde derivative represented by Chemical Formula 1 and a method of preparing the same. The binaphthol aldehyde derivative represented by Chemical Formula 1 enables various kinds of substituent groups to be very efficiently introduced into the hydrogen position of a 2' hydroxy group of 2,2'-binaphthol-3-aldehyde. The method is advantageous in that the binaphthol aldehyde derivative represented by Chemical Formula 1 can be prepared in a safe manner at low cost.