18531-92-5

Basic information

• Product Name: (aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid
• Synonyms: (aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid
• CAS NO: 18531-92-5
• Molecular Formula: C₂₂H₁₄O₆
• Molecular Weight: 374.34296
• Mol File: 18531-92-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: >290 °C(Solv: chloroform (67-66-3))
• Boiling Point: 570.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.528±0.06 g/cm3(Predicted)
• PKA: 2.42±0.30(Predicted)
• CAS DataBase Reference: (aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid(18531-92-5)
• EPA Substance Registry System: (aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid(18531-92-5)

Safety Data

• Hazardous Substances Data: 18531-92-5(Hazardous Substances Data)

Usage

Description

(aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid, also known as 1,1'-Binaphthyl-2,2'-dicarboxylic Acid, is a synthetic organic compound that belongs to the family of binaphthyl compounds. It is characterized by its binaphthalene core structure and two carboxylic acid functional groups, which contribute to its unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid is used as a chiral ligand for [application type] in asymmetric catalysis for [application reason] the synthesis of chiral pharmaceuticals and fine chemicals. Its stereochemistry makes it suitable for use in enantioselective reactions, where it can influence the outcome of chemical reactions to favor the production of a specific stereoisomer, which is crucial for the development of effective and safe medications.
Used in Materials Science:
(aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid is used as a key component in [application type] the development of advanced materials for [application reason] its unique structure and properties that can contribute to the creation of novel materials with specific characteristics, such as improved stability, reactivity, or selectivity.
Used in Organic Electronics:
(aR)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid is used as a building block in [application type] the design and synthesis of organic electronic devices for [application reason] its potential to enhance the performance of these devices by providing improved charge transport, stability, or other desired properties.

Upstream product

• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 35216-65-0 dimethyl 2,2'-dimethoxy-1,1'-naphthalene-3,3'-dicarboxylate 
• 98-95-3 nitrobenzene 
• 64-17-5 ethanol 
• 7705-08-0 iron(III) chloride 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 497106-69-1 (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 47644-69-9 dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Downstream Products

• 191-28-6 perixanthenoxanthene 
• 47644-69-9 dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate 
• 217327-65-6 2,2'-Bis-benzyloxy-[1,1']binaphthalenyl-3,3'-dicarboxylic acid dibenzyl ester 
• 217327-66-7 2,2'-Bis-benzyloxy-[1,1']binaphthalenyl-3,3'-dicarboxylic acid 

Relevant articles and documents

Properties of a binaphthyl-bridged porphyrin - Iron complex bearing hydroxy groups inside its cavity

Hydrogen-bond formation with the terminal oxygen atom is considered to be the basis of dioxygen molecule activation by cytochrome P450. In order to verify the effect of this hydrogen bond, we have undertaken the synthesis of a model complex: a binaphthyl-

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Design and synthesis of two-dimensional pillared MOF layers by connecting infinite one-dimensional chains via 4,4′-bipyridine

Two novel metal-organic frameworks, [Cd(Bna)(DMF)2(H 2O)2] n · nDMF (I) (Bna = 2,2′-dihydroxy-l,l′-dinaphthyl-3,3′-dicarboxylate) and [Cd(Bna)(Bipy)(DMF)2] n (II) (Bipy = 4,4′- bipyridine) have been synthesized under mild conditions and structurally characterized. Crystal structural analyses reveal that complex I adots a 1D spiral structure with DMF guest molecules in the spiral by hydrogen bondings. Complex II is constructed by -Cd-Bna-Cd- zigzag chains, which are further connected by Bipy into a 2D sheet. X-ray powder diffraction and thermogravimetric analyses for I and II show that they are highly themally stable in the solid state.

Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine

A simple and efficient method has been developed to resolve (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid [(±)-BINOL-3,3′-dicarboxylic acid] (±)-1 using inexpensive and readily accessible chiral resolving agent (1R,2R)-trans-cyclohexane-1,2-diamine 2. Enantiomers of BINOL-3,3′-dicarboxylic acid were obtained in good yields and enantiomeric purity, for example, (S)-(-)-1 was isolated in 34% yield with >99% ee and (R)-(+)-1 was obtained in 36% yield with >99% ee. The formation of diastereomeric salt A between (S)-BINOL-3,3′-dicarboxylic acid and (1R,2R)-trans-cyclohexane-1,2-diamine was ascertained by using IR, single crystal X-ray crystallography, and HRMS.

SYNTHETIC METHOD OF ENANTIOMERICALLY PURE 2,2'-DIHYDROXY-1,1'-BINAPHTHYL-3-CARBOXYLIC ACID

The present invention relates to a method for preparing enantiomerically pure compounds 1a and 1b of the following formula 1 from racemic compound 1 of the following formula 1. [formula 1] The compounds 1a and 1b of the above formula 1 respectively are im