122361-59-5

Basic information

• Product Name: (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid
• Synonyms: (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid;(R)-1,1'-binaphthyl-2,2'-disulfonic acid;1,1'-binaphthalene-2,2'-disulfonic acid
• CAS NO: 122361-59-5
• Molecular Formula: C₂₀H₁₄O₆S₂
• Molecular Weight: 414.45156
• Mol File: 122361-59-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid(122361-59-5)
• EPA Substance Registry System: (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid(122361-59-5)

Safety Data

• Hazardous Substances Data: 122361-59-5(Hazardous Substances Data)

Usage

Description

(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is a chiral compound characterized by two naphthalene rings and two sulfonic acid groups. It is widely recognized for its ability to induce asymmetry in chemical reactions, making it an indispensable tool in the synthesis of chiral pharmaceuticals and other fine chemicals.

Uses

Used in Asymmetric Synthesis:
(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is used as a chiral ligand in asymmetric synthesis reactions, particularly in the field of catalysis. It plays a crucial role in the production of chiral pharmaceuticals and other fine chemicals by facilitating the creation of enantiomerically pure compounds.
Used in Separation of Racemic Mixtures:
(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is used as a resolving agent for the separation of racemic mixtures into their enantiomeric forms. This application is vital in the pharmaceutical industry, where the desired biological activity is often associated with a specific enantiomer.
Used in Development of New Materials and Inorganic Catalysts:
(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is used in the development of new materials and inorganic catalysts due to its ability to form stable complexes with various metal ions. This property has led to its application in the advancement of asymmetric synthesis and the production of chiral compounds.
Used in Pharmaceutical Industry:
(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is used as a key component in the synthesis of chiral drugs, which are essential for the development of effective and targeted medications. (R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid's ability to induce asymmetry in chemical reactions is particularly valuable in this industry, as it allows for the production of enantiomerically pure compounds with specific biological activities.
Used in Chemical Research and Development:
(R)-[1,1']Binaphthalenyl-2,2'-disulfonic acid is used as a research tool in the development of new synthetic methods and the study of asymmetric catalysis. Its unique properties make it an invaluable asset in the ongoing quest to understand and improve the synthesis of chiral compounds.

Upstream product

• 55441-99-1 (R)-1,1′-binaphthalene-2,2′-dithiol 

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.

PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT

Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction

The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active -amino ketones, -amino esters, -lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1-binaphthyl-2,2-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction 2 1,1-Binaphthyl-2,2-disulfonic Acid (BINSA)-Pyridinium Salts 3 Lithium(I) Binaphtholate Salts 4 Magnesium(II) Binaphtholate Salts 5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids 6 Conclusions. Georg Thieme Verlag Stuttgart · New York.