2-dicyclohexylphosphino-1,1'-biphenyl, CAS No. 247940-06-3

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247940-06-3

Catalog No. EBD33881

CAS 247940-06-3

Name 2-dicyclohexylphosphino-1,1'-biphenyl

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Basic Information

Synonyms: 2-(Dicyclohexylphosphino)biphenyl (2-Biphenylyl)dicyclohexylphosphine biphenyl-2-yl(dicyclohexyl)phosphane CyJohnPhos 2-dicyclohexylphosphino-1,1'-biphenyl P,P-dicyclohexyl-o-biphenylphosphine biphenyl-2-yl-dicyclohexyl-phosphane 2-(Dicyclohexylphosphino)-biphenyl (2-biphenyl)dicyclohexylphosphine dicyclohexyl-phosphinobiphenyl CyclohexylJohnPhos 2-dicyclohexylphosphinyl-1,1 2-(dicyclohexylphosphino)-1,1 dicyclohexyl(o-biphenyl)phosphine o-(dicyclohexylphosphino)biphenyl biphenyl-2-yldicyclohexylphosphine -biphenyl-2-yl)dicyclohexylphosphine

Molecular Formula: C24H31P

Molecular Weight: 350.48

MDL Number: MFCD01862441

Categories: Synthetic Chemistry > Catalysts and Ligands > Phosphorus Ligands Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds

Product Description:

2-(Dicyclohexylphosphino)biphenyl is a monodentate, electron-rich triarylphosphine ligand. It is a key precursor in the synthesis of the widely used Buchwald-type biarylphosphine ligands, such as SPhos and XPhos, which are generated by further functionalization of the biphenyl backbone. The compound itself, often referred to by its precursor role, features a bulky and electron-donating dicyclohexylphosphino group attached to a biphenyl system. This phosphine ligand and its derivatives are extensively employed in palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura, Buchwald-Hartwig amination, and Negishi couplings. The steric bulk and electron-donating properties of the phosphine enhance the catalytic activity and stability of the palladium center, enabling efficient coupling of aryl chlorides and other challenging substrates under mild conditions. It is a fundamental building block in organometallic chemistry and catalyst design. As a specialty chemical, it is primarily used in research and development for pharmaceutical and advanced material synthesis. Handling requires precautions under an inert atmosphere (e.g., nitrogen or argon) due to its sensitivity to air and moisture, which can lead to oxidation.

Physical Properties

Melting Point: 102-106 °C(lit.)

Boiling Point: 499.5 °C at 760 mmHg

Flash Point: 271.7 °C

Analytical Data

Appearance: white to light yellow crystal powder