Tricyclohexyl phosphine
[CAS# 2622-14-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Tricyclohexyl phosphine
• Molecular Formula: C₁₈H₃₃P
• Molecular Weight: 280.43
• CAS Registry Number: 2622-14-2
• EC Number: 220-069-2
• SMILES: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

Properties

• Melting point: 77-83 °C
• Flash point: 11 °C

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS09 Danger
• Risk Statements: H252-H315-H319-H335-H411
• Safety Statements: P235-P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P407-P410-P413-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Self-heating substances or mixtures	Self-heat.	1	H251
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Tricyclohexylphosphine (PCy3) is an important organophosphorus compound recognized for its key roles in organic synthesis, catalysis, and materials science. Chemically, tricyclohexylphosphine is a trialkylphosphine with the molecular formula C18H33P. It consists of a phosphorus atom bonded to three cyclohexyl groups, which imparts steric bulk and provides stability in a variety of chemical environments. This structural feature makes PCy3 a valuable ligand in coordination chemistry, where it can stabilize transition metal complexes through its electron-donating and sterically demanding properties.

The discovery of tricyclohexylphosphine dates back to the mid-20th century, evolving from the synthesis and study of phosphorus-based ligands and their applications in catalytic reactions. Researchers consider PCy3 to be a versatile ligand capable of forming stable complexes with a wide range of transition metals, thereby improving catalytic efficiency and selectivity in a variety of organic transformations.

In homogeneous catalysis, PCy3 is used as a ligand for transition metal-catalyzed reactions such as cross-coupling reactions, hydrogenations, and C-H activations. Its ability to alter the electronic and steric environment around the metal center helps control reaction pathways and improve the yield and stereochemical outcomes of synthetic processes. This catalytic versatility makes PCy3 a cornerstone for the development of sustainable and efficient organic chemical synthesis methods.

Tricyclohexylphosphine is also useful in materials science, particularly in the synthesis of functional materials and coordination polymers. Its use as a building block in molecular design allows the creation of tailored materials with specific optical, electronic, and magnetic properties. By incorporating PCy3 into polymer matrices or metal-organic frameworks (MOFs), researchers can design materials for a variety of applications, from sensors and catalytic supports to advanced materials for energy storage and conversion.

In addition, PCy3 is used in the pharmaceutical industry to synthesize drug intermediates and active pharmaceutical ingredients (APIs). Its role in promoting complex organic reactions under mild conditions helps to efficiently produce candidate drugs and therapeutics.

The discovery and continued research of tricyclohexylphosphine highlights its importance as a versatile chemical tool in modern chemistry and materials science. Its unique combination of stereo and electronic properties continues to inspire new developments in catalysis, materials design, and medicinal chemistry, promising further innovations and applications in diverse scientific disciplines.

References

2024. Recent Advances in C-O Bond Cleavage of Aryl, Vinyl, and Benzylic Ethers. Topics in Current Chemistry, 382(4).
DOI: 10.1007/s41061-024-00484-7

2023. Nickel-catalyzed regioselective B(3,4,5,6)-H tetra-alkylation of o-carboranes. Science China Chemistry, 66(12).
DOI: 10.1007/s11426-023-1750-0

2023. Poly[4-(1′-pyrenyl)styrene]: synthesis, photophysical properties, and practical application. Russian Chemical Bulletin, 72(11).
DOI: 10.1007/s11172-023-4077-6