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Merck
CN

924350

Tris(1-adamantyl)phosphine

Umicore, powder

Synonym(s):

Tris(1-adamantyl)phosphine, P(Ad)3

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About This Item

Empirical Formula (Hill Notation):
C30H45P
CAS Number:
Molecular Weight:
436.65
UNSPSC Code:
12352200
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Product Name

Tris(1-adamantyl)phosphine, Umicore

Quality Level

form

powder

reaction suitability

reagent type: ligand

mp

>240 °C

functional group

phosphine

Related Categories

Application

Tris(1-adamantyl)phosphine, P(Ad)3, is a crystalline solid phosphine ligand that exhibits electron releasing character greater than most alkylphosphines. This ligand had demonstrated uses in many cross-coupling reactions, including the Suzuki-Miyaura coupling.
P(Ad)3 has been used in:
  • The Suzuki-Miyaura coupling of base-sensitive polyfluoroaryl boronic acids.
  • The long-range isomerization of alkenyl alcohols.
  • The Ni mediated polymerization of ethylene.

Preparation Note

Do not store above 25°C (77°F). Store in a tightly closed original container under dry inert gas, protected from direct sunlight in a dry, cool and well-ventilated area.

Legal Information

Product of Umicore

This product, its manufacturing or use, is the subject of one or more issued or pending U.S. Patents (and foreign equivalents) owned or controlled by Umicore PMC. The purchase of this product from Umicore PMC through Sigma-Aldrich, its affiliates or their authorized distributors conveys to the buyer a limited, one-time, non-exclusive, non-transferable, non-assignable license. Buyer′s use of this product may infringe patents owned or controlled by third parties. It is the sole responsibility of buyer to ensure that its use of the product does not infringe the patent rights of third parties or exceed the scope of the license granted herein.

Additional information available at www.pmc.umicore.com

Regulatory Information

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Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds
Liye Chen, Peng Ren, and Brad P. Carrow
Journal of the American Chemical Society, Volume 138, Issue 20, 6392-6395 (2016)
Simone Scaringi et al.
Journal of the American Chemical Society, 146(27), 18606-18615 (2024-06-28)
In recent years, progress has been made in the development of catalytic methods that allow remote functionalizations based on alkene isomerization. In contrast, protocols based on alkyne isomerization are comparatively rare. Herein, we report a general Pd-catalyzed long-range isomerization of
A highly active Ni(II)-triadamantylphosphine catalyst for ultrahigh-molecular-weight polyethylene synthesis
Kocen A L, et al.
Nature Communications, 10(1), 438-438 (2019)
Liye Chen et al.
Journal of the American Chemical Society, 139(36), 12418-12421 (2017-09-02)
Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd3-Pd catalyst that proceeds at rt in the

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