Tricyclohexylphosphine
Tricyclohexylphosphine (CAS: 2622-14-2), with the molecular formula (C6H11)3P and a molecular weight of 280.43 g/mol, is a sterically demanding phosphine ligand. It is widely employed in homogeneous catalysis, particularly in palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Heck, and Sonogashira couplings. Its bulky nature influences catalytic activity and selectivity, making it a valuable reagent in organic synthesis.
- IUPAC
- P(Cy)3,PCy3
- Synonyms
- Tricyclohexylphosphine
Palladium-Catalyzed Cross-Coupling Reactions
Tricyclohexylphosphine serves as an effective ligand in various palladium-catalyzed cross-coupling reactions. It is particularly noted for its use in the Suzuki-Miyaura coupling of aryl bromides and chlorides, and in the Heck reaction.
Ligand in Catalytic Systems
This bulky phosphine ligand is employed in conjunction with palladium catalysts for reactions such as the Sonogashira coupling. Its steric bulk can enhance reaction efficiency and influence regioselectivity in complex synthetic pathways.
Synthesis of Malononitrile Derivatives
It is utilised as a ligand in the palladium-catalyzed coupling of malononitrile with aryl halides. This application highlights its role in the formation of specific organic structures.
| Molecular weight | 280.43 |
|---|---|
| Linear formula | (C6H11)3P |
| Concentration | 20 wt. % in toluene |
| Application | Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides.1 Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides.2 |
| Melting point | 81-83 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
| Ligand For | Heck ReactionHiyama CouplingSonogashira CouplingSuzuki-Miyaura Coupling |
|---|
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Tricyclohexylphosphine used for?
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Tricyclohexylphosphine is primarily used as a bulky phosphine ligand in palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura, Heck, and Sonogashira couplings, and in the synthesis of malononitrile derivatives.
What is the CAS number and formula for Tricyclohexylphosphine?
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The CAS number for Tricyclohexylphosphine is 2622-14-2, and its linear formula is (C6H11)3P.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Tricyclohexylphosphine typically in research or technical grades. The exact assay and purity are detailed on the Certificate of Analysis provided with each order. We do not represent this product as USP, BP, or EP grade.
How should Tricyclohexylphosphine be handled safely?
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Tricyclohexylphosphine is classified as a warning substance, causing skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Handle with appropriate personal protective equipment, including a dust mask (type N95 or equivalent), eyeshields, and gloves, in a well-ventilated area.
Is Tricyclohexylphosphine a controlled substance?
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The provided data does not indicate that Tricyclohexylphosphine is a controlled substance.
How is Tricyclohexylphosphine shipped and exported?
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Tech Serve Solutions is an experienced global supplier and exporter of fine chemicals, ensuring appropriate packaging and documentation for international shipments of Tricyclohexylphosphine.
How can I request a sample or quote for Tricyclohexylphosphine?
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To request a sample or a quotation for Tricyclohexylphosphine, please contact our sales team via the website or through the provided contact details, specifying the CAS number 2622-14-2.
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