349149-08-2

Basic information

• Product Name: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde
• Synonyms: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde
• CAS NO: 349149-08-2
• Molecular Formula: C₂₁H₁₄O₃
• Molecular Weight: 314.33406
• Mol File: 349149-08-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(349149-08-2)
• EPA Substance Registry System: R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde(349149-08-2)

Safety Data

• Hazardous Substances Data: 349149-08-2(Hazardous Substances Data)

Usage

Description

R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is a chiral binaphthol compound with the molecular formula C20H14O3. It features a molecular structure comprising two naphthalene rings connected by a carbon-carbon bond, adorned with two hydroxyl (-OH) groups on the naphthalene rings and an aldehyde group (-CHO) at the 3 position on one of the rings. This unique arrangement endows it with distinctive structural and chemical properties, making it a valuable chiral building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde serves as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of enantiomerically pure molecules, which is crucial in drug development as different enantiomers can exhibit distinct biological activities and pharmacokinetics.
Used in Organic Synthesis:
In the field of organic synthesis, R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde is utilized as a key intermediate for the preparation of a wide range of organic molecules. Its reactive functional groups, such as the aldehyde and hydroxyl groups, facilitate various chemical reactions, enabling the synthesis of complex organic compounds with potential applications in materials science, agrochemicals, and other industries.
Used in Chiral Catalysts:
The chiral nature of R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde makes it a suitable candidate for the development of chiral catalysts. These catalysts are essential in asymmetric synthesis, a technique used to produce enantiomerically enriched compounds, which is particularly important in the production of pharmaceuticals and agrochemicals where the desired biological activity is often associated with a specific enantiomer.
Used in Analytical Chemistry:
R-2,2'-dihydroxy-[1,1'-Binaphthalene]-3-carboxaldehyde can also be employed in analytical chemistry as a chiral derivatizing agent. It can react with enantiomers of a compound to form diastereomers, which can be separated and analyzed using techniques such as chromatography. This allows for the determination of enantiomeric purity and the study of the stereochemistry of various compounds.

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

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.

A trivalent iron ion fluorescent probe compound, and its preparation and use

The invention relates to a ferric fluorescent probe compound as well as a preparation method and application thereof. The ferric fluorescent probe compound has the structure in formula I in the specification. The preparation method comprises the following steps: mixing rhodamine B with anhydrous ethanediamine and refluxing in ethyl alcohol to prepare amide of rhodamine; protecting hydroxyl of binaphthol by chloromethyl methyl ether, reacting with N,N-dimethylformamide under the action of butyl lithium, and removing methyl of methyl ether by hydrochloric acid to obtain binaphthol with aldehyde group; finally refluxing the amide of rhodamine and the binaphthol with aldehyde group in ethyl alcohol and washing to obtain the pure ferric fluorescent probe compound. The probe compound has favorable selectivity and sensitivity for the ferric ions, is simple to treat before sample detection and free of causing toxicity to cells, and is used for detecting the ferric ions in the water environment or the biological cells.

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.