Butyldi-1-adamantylphosphine

C24H39P

358.54

Butyldi-1-adamantylphosphine is a highly effective tertiary phosphine ligand widely used in palladium-catalyzed cross-coupling reactions. It features a butyl group and two 1-adamantyl groups attached to a central phosphorus atom, creating a sterically demanding and electron-rich phosphine. The ligand provides excellent steric and electronic properties for challenging coupling reactions, particularly with sterically hindered or electron-rich substrates. It is commonly employed in combination with palladium sources to form highly active catalysts for Suzuki-Miyaura couplings, Buchwald-Hartwig aminations, and other C-C and C-N bond-forming reactions. The bulky di-1-adamantyl substituents create a unique steric environment that enhances catalyst stability and reactivity, while the butyl group imparts favorable solubility characteristics. This ligand is bench-stable, soluble in most organic solvents, and is a valuable component in modern pharmaceutical synthesis and organic chemistry research.

Catacxium A; n-Butyl-di(1-adamantyl)phosphine; Di(1-adamantyl)-n-butylphosphine; Bis(adamantan-1-yl)(butyl)phosphane; Di(adamantan-1-yl)(butyl)phosphine; Butyldi(1-adamantanyl)phosphine; Di-1-Adamantyl-n-butylphosphine; Butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine; n-Butyl-di-adamantylphosphine

bis(1-adamantyl)-butylphosphane

CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5

InChI=1S/C24H39P/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24/h17-22H,2-16H2,1H3

HTJWUNNIRKDDIV-UHFFFAOYSA-N

449.6±12.0 °C at 760 mmHg

100°C

98%

White to yellow powder

Store at RT, under inert atmosphere

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Warning