Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate
[CAS# 870245-84-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate
• Synonyms: sodium 4-(2-dicyclohexylphosphanylphenyl)-3,5-di(propan-2-yl)benzenesulfonate;hydrate
• Molecular Formula: C₃₀H₄₂O₃PS^.Na
• Molecular Weight: 536.68
• CAS Registry Number: 870245-84-4
• SMILES: CC(C)C1=CC(=CC(=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C)S(=O)(=O)[O-].O.[Na+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335-H413
• Precautionary Statements: P261-P264-P271-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Discovory and Applicatios

Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate is a specialized compound in the field of organophosphorus chemistry and catalysis. Its structure, featuring a sulfonate group and a phosphine ligand, makes it valuable for a variety of applications in chemical synthesis and catalysis.

The synthesis of sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate involves several key steps. Initially, the biphenyl scaffold is functionalized to incorporate the phosphine ligand and the sulfonate group. The dicyclohexylphosphine is introduced through a phosphination reaction, where the biphenyl compound reacts with dicyclohexylphosphine to form the desired ligand. The sulfonate group is then introduced, often through a sulfonation reaction, which replaces a hydrogen atom with a sulfonate group at the 4-position of the biphenyl ring. Finally, the sodium salt is formed by neutralizing the sulfonic acid group with sodium hydroxide.

This compound's unique combination of a phosphine ligand and a sulfonate group provides distinctive electronic and steric properties that are useful in catalysis. The phosphine moiety can stabilize transition metals in catalytic cycles, while the sulfonate group enhances the solubility of the compound in aqueous media, making it suitable for use in aqueous phase reactions.

One of the primary applications of sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate is in transition metal-catalyzed reactions. The compound is often employed as a ligand in palladium-catalyzed cross-coupling reactions, such as Suzuki and Heck reactions. In these reactions, the phosphine ligand coordinates to the palladium center, facilitating the formation of carbon-carbon bonds between reactants. The sulfonate group helps maintain the solubility of the catalyst in aqueous solvents, making the reactions more environmentally friendly and accessible.

Additionally, this compound is used in asymmetric synthesis, where it serves as a ligand in chiral catalysts. The specific arrangement of the ligand allows for the selective formation of chiral products, which is crucial in the synthesis of pharmaceuticals and fine chemicals. The ligand's ability to influence the stereochemistry of reactions enhances the efficiency and selectivity of asymmetric transformations.

Furthermore, sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate is valuable in materials science. Its metal-complexing properties are utilized to create functional materials with specific electronic and optical properties. These materials can be employed in various applications, including sensors and electronic devices.

In conclusion, sodium 2'-(dicyclohexylphosphino)-2,6-diisopropylbiphenyl-4-sulfonate is a versatile compound with significant applications in catalysis, asymmetric synthesis, and materials science. Its structure and properties enable it to play a crucial role in advancing chemical reactions and developing new materials.