674285-08-6

Basic information

• Product Name: (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane
• Synonyms: (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane;(1R,2R)-[N,N'-Bis(2',3'-dihydroxybenzylidene)]-1,2-diaminocyclohexane 95%
• CAS NO: 674285-08-6
• Molecular Formula: C20H22N2O4
• Molecular Weight: 354.39968
• Mol File: 674285-08-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 94-116°C
• Boiling Point: 603.1±55.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 11.04±0.10(Predicted)
• CAS DataBase Reference: (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane(674285-08-6)
• EPA Substance Registry System: (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane(674285-08-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 2
• Hazardous Substances Data: 674285-08-6(Hazardous Substances Data)

Usage

Description

(1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane, commonly known as a salen ligand, is a chiral compound that features a diaminocyclohexane core with two N,N′-bis(2′,3′-dihydroxybenzylidene) groups attached to it. This unique structure endows it with versatile properties and makes it a significant compound in the field of coordination chemistry, where it acts as a chelating agent.

Uses

Used in Catalysis:
(1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane is used as a chelating agent in catalysis for its ability to bind metal ions, forming stable complexes that can act as catalysts in various chemical reactions. Its chiral nature allows it to influence the stereochemistry of the catalyzed reactions, making it particularly useful in asymmetric catalysis.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane is used as a ligand to create enantioselective catalysts. The stereochemistry of the ligand plays a crucial role in determining the selectivity of the catalyzed reaction, enabling the production of chiral compounds with high enantiomeric purity.
Used in Coordination Chemistry:
(1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane is utilized as a chelating agent in coordination chemistry for its ability to form complexes with metal ions. These complexes have potential applications in various areas, including catalysis, sensing, and materials science.
Used in Chemical Reactions and Processes:
(1R,2R)-[N,N′-Bis(2′,3′-dihydroxybenzylidene)]-1,2-diaMinocyclohexane is used as a versatile component in a wide range of chemical reactions and processes due to its unique structure and properties. Its ability to chelate metal ions and influence the stereochemistry of reactions makes it an important player in the synthesis of complex organic molecules and the development of new catalytic systems.

Upstream product

• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 191480-63-4 (1R,2R)-1,2-diaminocyclohexane monohydrochloride 
• 1121-22-8 trans-1,2-Diaminocyclohexane 

Relevant articles and documents

Dicatechol-diimines: Easily accessible ligands for the self-assembly of dinuclear triple-stranded helicates

Dicatechol ligands 3b-g-H4 are simply prepared by imine formation of 2,3-dihydroxybenzaldehyde 2 with a series of different diamines 1b-g. An X-ray structural analysis was obtained for the butyl-bridged compound 3e-H4, showing an intramolecular proton transfer and the formation of a chinoidic keto-amine structure. The dicatechol derivatives 3b-g-H4 form dinuclear triple-stranded helicates M4[(3)3Ti2] with titanium(IV) ions in the presence of alkali-metal carbonate. For the phenyl- and the trans-1,4-cyclohexyl-bridged complexes, K4[(3b)3Ti2] and Na4[(3f)3Ti2], X-ray structures were obtained.