Dicyclohexylphosphine
[CAS# 829-84-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Dicyclohexylphosphine
• Molecular Formula: C₁₂H₂₃P
• Molecular Weight: 198.28
• CAS Registry Number: 829-84-5
• EC Number: 212-590-9
• SMILES: C1CCC(CC1)PC2CCCCC2

Properties

• Melting point: 129 °C (8mmHg)
• Refractive index: 1.516

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H225-H250-H301+H311+H331-H301-H311-H314-H319-H331-H411
• Safety Statements: P210-P222-P231-P233-P240-P241-P242-P243-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P330+P331-P302+P335+P334-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P316-P321-P330-P337+P317-P361+P364-P363-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Pyrophoric liquids	Pyr. Liq.	1	H250
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Flammable liquids	Flam. Liq.	2	H225
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	1	H224
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Dicyclohexylphosphine is a notable organophosphorus compound with significant applications in chemistry, particularly in catalysis and organic synthesis. This chemical substance is characterized by the presence of two cyclohexyl groups attached to a central phosphorus atom, forming a stable phosphine ligand. The synthesis of dicyclohexylphosphine involves the reaction of cyclohexylmagnesium bromide with a phosphorus trichloride precursor, resulting in the formation of the desired phosphine.

The discovery of dicyclohexylphosphine can be traced back to efforts aimed at developing new ligands for transition metal complexes. Its structure, which incorporates bulky cyclohexyl groups, imparts steric hindrance around the phosphorus atom. This steric bulk is crucial in stabilizing metal complexes and influencing their reactivity. The presence of these bulky groups helps to reduce the likelihood of ligand dissociation, thereby enhancing the stability of the metal center.

In terms of applications, dicyclohexylphosphine is widely used as a ligand in various catalytic processes. Its effectiveness as a ligand is particularly evident in transition metal catalysis, where it plays a crucial role in facilitating reactions such as hydrogenation, cross-coupling, and hydroformylation. The bulky cyclohexyl groups provide significant steric protection, making the ligand highly effective in stabilizing metal centers and promoting specific catalytic transformations.

Additionally, dicyclohexylphosphine is employed in the synthesis of complex organic molecules. It is used to form organometallic compounds that serve as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. The ligand's ability to coordinate with various metals allows for the formation of a range of metal complexes, each with tailored reactivity suitable for different synthetic applications.

The compound also finds use in material science, particularly in the development of advanced materials with specific properties. The phosphine's role in stabilizing metal centers can be exploited to create materials with desirable mechanical, electrical, or catalytic properties.

Overall, dicyclohexylphosphine represents an important advancement in the field of organophosphorus chemistry. Its discovery and applications highlight the significance of phosphine ligands in enhancing the stability and reactivity of metal complexes, making it a valuable tool in both industrial and academic research.

References

2020. Copper-catalyzed C-P cross-coupling of arylmethyl quaternary ammonium salts via C-N bond cleavage. Monatshefte für Chemie - Chemical Monthly, 151(1).
DOI: 10.1007/s00706-019-02535-y

2017. Preparation of Aryl(dicyclohexyl)phosphines by C-P Bond-Forming Cross-Coupling in Water Catalyzed by an Amphiphilic-Resin-Supported Palladium Complex. Synlett, 28(16).
DOI: 10.1055/s-0036-1590926

2008. Phosphorus derivatives of carboranes as ligands for Pd-catalyzed cross-coupling reactions. Russian Chemical Bulletin, 57(11).
DOI: 10.1007/s11172-008-0326-y