(2-Biphenyl)di-1-adamantylphosphine

CAS No. 224311-55-1
Cat. No. CS-0108697
Molecule weight454.63
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(2-Biphenyl)di-1-adamantylphosphine|CS-0108697

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General Information

CAS No. 224311-55-1
Cat. No. CS-0108697
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₂H₃₉P
Molecular Weight 454.63
Synonym(s) 2-[Bis(1-adamantyl)phosphino]biphenyl
SMILES [C@@H]12C[C@H](C3)C[C@H](CC3(P(C4(C[C@@H]5C6)C[C@H](C5)C[C@H]6C4)C7=CC=CC=C7C8=CC=CC=C8)C2)C1

Description

(2-Biphenyl)di-1-adamantylphosphine features a sterically shielded phosphine center with enhanced stability and electron-donating capacity. This bulky ligand facilitates efficient transition metal catalysis, particularly in cross-coupling reactions under air-sensitive conditions. The 1-adamantyl groups provide exceptional steric protection, minimizing decomposition while maintaining high reactivity.

Application

(2-Biphenyl)di-1-adamantylphosphine serves as a sterically hindered, electron-rich phosphine ligand that enables efficient cross-coupling reactions in palladium-catalyzed processes. Its robust adamantyl groups confer exceptional thermal and oxidative stability, while the biphenyl moiety enhances π-stacking interactions and coordination strength. This ligand facilitates reliable coupling of challenging substrates, including sterically congested aryl halides and heteroaryl electrophiles, with improved catalyst turnover and reduced decomposition—ideal for scalable synthesis and complex molecule assembly.

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H319
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

TPSA 0
LogP 8.3984
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 4

Key Words

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(2-Biphenyl)di-1-adamantylphosphine

CAS No. 224311-55-1

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