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Description
1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole from TCI, listed under CAS number 628333-86-8, is a phosphine ligand built on a pyrazole framework and designed for the catalysis of cross-coupling reactions. The molecule combines an electron-rich phosphorus atom bearing di-tert-butyl groups with a diphenyl-substituted pyrazole ring, the two connected through a phenylene bridge. In the laboratory, this compound acts as a supporting ligand for transition metals, particularly palladium, where its task is to form the active catalytic complex and to direct the course of the catalytic cycle in reactions that build carbon–carbon and carbon–heteroatom bonds.
The properties that make this ligand a preferred choice are the combination of high basicity and substantial steric bulk contributed by the di-tert-butylphosphino group. High basicity accelerates the oxidative addition step on less reactive substrates, while the steric bulk promotes the reductive elimination step so that the catalytic cycle turns over more rapidly. The pyrazole ring supplies an additional donor nitrogen atom together with a rigid aromatic framework, giving a directed coordination environment around the metal centre. A structure of this kind generally allows low catalyst loadings and a broad substrate scope.
In Indonesian laboratories, a ligand of this type is typically used in synthetic and methodology work where a palladium-catalysed coupling has to be assembled from the metal precursor and the ligand in situ, or pre-formed as a defined complex before use. It suits organic synthesis groups in universities and research institutes, as well as process and formulation development laboratories that prepare intermediates on a small scale and need a coupling system that performs reliably on demanding substrates.
Laboratory Applications
Suzuki–Miyaura coupling: the high basicity of the di-tert-butylphosphino group assists oxidative addition on less reactive aryl substrates, while the steric bulk speeds reductive elimination and turnover.
Buchwald–Hartwig type carbon–nitrogen bond formation: the electron-rich phosphorus centre and rigid pyrazole framework give the directed coordination environment needed for reliable amination of aryl partners.
General carbon–carbon bond construction: the ligand forms active catalytic complexes with palladium and steers the catalytic cycle, supporting couplings that would otherwise stall on hindered substrates.
Carbon–heteroatom coupling methodology studies: the additional donor nitrogen atom of the pyrazole ring offers a defined coordination geometry that researchers can exploit when screening reaction conditions.
Low-loading catalysis work: because the structure generally permits reduced catalyst charges and broad substrate scope, it suits laboratories optimising ligand-to-metal ratios and catalyst economy.
Specifications
Brand: TCI
CAS number: 628333-86-8
Category: Chemistry > Catalysis and Inorganic Chemistry > Cross-Coupling [Catalysis]
Chemical name: 1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole
Pack sizes: available in the standard research-scale pack sizes offered by the manufacturer; please confirm the packaging option required when ordering.
Storage: keep in the closed original container under the conditions stated on the manufacturer's label and safety data sheet.
Handling and Storage
Store the product in its original tightly closed container, kept in a cool, dry and well-ventilated place away from heat, ignition sources and incompatible materials, and follow the specific storage conditions printed on the manufacturer's label and safety data sheet. As with other trialkylphosphine ligands, minimise exposure to air and moisture during handling; use tightly sealed glass or the supplied original containers rather than transferring to open vessels. Weigh and dispense in a fume hood using an inert atmosphere where the protocol calls for it, and wear a laboratory coat, safety glasses and suitable chemical-resistant gloves. Keep the container closed when not in use, label all secondary containers clearly, and dispose of residues and contaminated consumables through the laboratory's chemical waste procedure. Consult the manufacturer's safety data sheet before first use.
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![1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole (CAS 628333-86-8) - TCI D3834 - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510D3834.jpg?v=1767106644&width=1445)
