80703-23-7

Basic information

• Product Name: R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID
• Synonyms: R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID;(1R)-[1,1'-Binaphthalene]-2,2'-dicarboxylic acid;R-[1,1'-binaphthalene]-2,2'-dicarboxylic acid
• CAS NO: 80703-23-7
• Molecular Formula: C₂₂H₁₄O₄
• Molecular Weight: 342.34416
• Mol File: 80703-23-7.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 493.3 °C at 760 mmHg
• Flash Point: 266.2 °C
• Appearance: /
• Density: 1.380
• PKA: 3.66±0.30(Predicted)
• CAS DataBase Reference: R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID(80703-23-7)
• EPA Substance Registry System: R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID(80703-23-7)

Safety Data

• Hazardous Substances Data: 80703-23-7(Hazardous Substances Data)

Usage

General Description

R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID is a chemical compound with the molecular formula C26H16O4. It is a derivative of binaphthyl, a type of organic compound with two naphthyl groups connected by a central bond. R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID is often used as a chiral ligand in asymmetric catalysis, particularly in the field of organic synthesis. It has the ability to form complexes with metal ions, which are then used to catalyze various chemical reactions with high levels of stereocontrol. R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID has also been studied for its potential applications in the development of new pharmaceuticals and materials.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 85464-88-6 [1,1']binaphthyl-2,2'-dicarboxylic acid dimethyl ester 
• 138488-70-7 Methyl 1-chloro-2-naphthoate 
• 93530-99-5 2,2'-bis[2-(4,4-dimethyl-Δ²-oxazolinyl)]-1,1'-binaphthyl 
• 76373-16-5 1-Bromo-naphthalene-2-carboxylic acid 1-methyl-heptyl ester 
• 76373-12-1 l-menthyl 1-bromo-2-naphthoate 
• 76373-13-2 1-Bromo-naphthalene-2-carboxylic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 76373-14-3 1-Bromo-naphthalene-2-carboxylic acid 1-phenyl-ethyl ester 
• 76373-14-3 1-Bromo-naphthalene-2-carboxylic acid 1-phenyl-ethyl ester 
• 153433-31-9 2'-hydroxymethyl-1,1'-binaphthalene-2-carboxylic acid 
• 153433-35-3 2'-isopropyl 2-hydrogen 1,1'-binaphthyl-2,2'-dicarboxylate 
• 124-38-9 carbon dioxide 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 641-13-4 anthanthrone 
• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 86457-66-1 rac-2,2'-Binaphthyldicarboxylic acid dichloride 
• 246140-16-9 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid monoglycidyl ester 
• 881812-14-2 (R,R,RS)-2,6-bis(2-biphenyl)-4-methyl-4,5-dihydro-3H-4-azacyclohepta[2,1-a;3,4a']dinaphthalene 
• 881812-20-0 4-methyl-2,6-bis-(2-phenyl-naphthalen-1-yl)-4,5-dihydro-3H-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 881812-36-8 2,6-bis-[2,4-bis-(4-trifluoromethyl-phenyl)-naphthalen-1-yl]-4-methyl-4,5-dihydro-3H-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalene 

Relevant articles and documents

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid

The invention relates to the technical field of bromination, hydrolysis, oxidation and coupling reaction in organic synthesis, particularly a synthesis method of an axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method comprises the following steps: synthesizing a compound 1-bromo-2-methylnaphthalene from an initial raw material 2-bromomethylnaphthalene, carrying out bromination, hydrolysis and oxidation on the 1-bromo-2-methylnaphthalene to obtain 1-bromo-2-naphthoic acid, generating an ester under the actions of methanol and thionyl chloride, protecting the carboxyl group, carrying out Ullmann reaction under the action of copper powder to perform coupling, carrying out hydrolysis to obtain 2,2'-dinaphthyl-1,1'-dicarboxylic acid, and finally, resolving to obtain the (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method is simple to operate, and has the advantages of higher yield and favorable economical efficiency.

Design and synthesis of new stable fluorenyl-based radicals

Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.