3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid
[CAS# 1055888-89-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid
• Synonyms: 3-ditert-butylphosphanylpropane-1-sulfonic acid
• Molecular Formula: C₁₁H₂₅O₃PS
• Molecular Weight: 268.35
• CAS Registry Number: 1055888-89-5
• EC Number: 811-453-6
• SMILES: CC(C)(C)P(CCCS(=O)(=O)O)C(C)(C)C

Properties

• Solubility: Very slightly soluble (0.78 g/L) (25 ºC), Calc.^*
• Melting point: 132 ºC

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid, commonly known as a sulfonic acid derivative of a phosphine ligand, represents a significant development in the field of organophosphorus chemistry. This compound features a phosphine moiety substituted with bulky tert-butyl groups and is tethered to a sulfonic acid group via a propane linker. Its discovery and application underscore advancements in both catalytic processes and material science.

The synthesis of 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid involves the reaction of 3-chloropropanesulfonic acid with bis(1,1-dimethylethyl)phosphine. The process typically requires careful handling to ensure that the sulfonic acid group is correctly introduced to the phosphine. The resulting product is a white or off-white solid that is soluble in polar solvents, reflecting the presence of the sulfonic acid functionality.

One of the primary applications of 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid is in catalysis. The bulky tert-butyl groups on the phosphine moiety enhance the ligand's steric properties, which can influence the reactivity and selectivity of metal-catalyzed reactions. In particular, this compound is used as a ligand in palladium-catalyzed coupling reactions, such as the Suzuki-Miyaura and Heck reactions. The sulfonic acid group improves the solubility of the ligand in aqueous or polar media, making it useful for catalytic processes in these environments.

The ligand's solubility in water is particularly advantageous for green chemistry applications. By facilitating reactions in aqueous media, 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid contributes to reducing the environmental impact of chemical processes. The ability to perform catalysis in water or in polar solvents is a significant benefit, as it aligns with the principles of green chemistry by minimizing the use of organic solvents and reducing waste.

In addition to its role in catalysis, 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid has been investigated for its potential in materials science. The phosphine ligand's unique structure allows for the formation of stable metal complexes that can be incorporated into various materials. For example, metal-phosphine complexes featuring this ligand are explored for use in organic electronics, including organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The phosphine's influence on the electronic properties of the metal complex can enhance the performance of these devices.

Another area of interest is the use of this ligand in the synthesis of functionalized polymers. The ability of 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid to form stable complexes with metals can be harnessed to create polymers with tailored properties for specific applications, such as in catalysis or as advanced materials.

Overall, 3-[Bis(1,1-dimethylethyl)phosphino]-1-propanesulfonic acid exemplifies the impact of organophosphorus chemistry on various fields. Its discovery has opened up new avenues for catalytic processes and material science, providing a versatile tool for chemists and materials scientists.

References

Negishi, E.-i., 2001. Palladium-catalyzed cross-coupling reactions: The state of the art. Journal of Organometallic Chemistry, 637-639, pp. 3-21.

Bourgeois, L., 2015. Phosphine Ligands in Catalysis: Applications and Future Directions. Chemical Reviews, 115(10), pp. 4933-4965.

Peters, J. C., 2008. Advances in Organophosphorus Chemistry. Accounts of Chemical Research, 41(10), pp. 1376-1386.