651885

Dicyclohexyl(2-methylphenyl)phosphine

95%

• Synonym(s): (o-Tolyl)dicyclohexylphosphine
• Empirical Formula (Hill Notation): C₁₉H₂₉P
• CAS Number: 173593-25-4
• Molecular Weight: 288.41
• MDL number: MFCD08276773
• UNSPSC Code: 12352002
• PubChem Substance ID: 24883863

Properties

• assay: 95%
• form: solid
• reaction suitability: reaction type: Cross Couplings
• mp: 90-93 °C
• functional group: phosphine
• SMILES string: Cc1ccccc1P(C2CCCCC2)C3CCCCC3
• InChI: 1S/C19H29P/c1-16-10-8-9-15-19(16)20(17-11-4-2-5-12-17)18-13-6-3-7-14-18/h8-10,15,17-18H,2-7,11-14H2,1H3
• InChI key: MKHYBAIPMJGEQO-UHFFFAOYSA-N

Description

General description

Dicyclohexyl(2-methylphenyl)phosphine is a phosphorus ligand with some unique features like high melting point, ease of handle and less susceptibility for oxidation, making it an ideal catalyst in coupling reactions.[1]

Application

Cocatalyst for:

• Nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates

Catalyst for:

• Coupling of nonactivated and deactivated aryl chlorides with arylboronic acid
• Preparation of (alkyl)(aryl)phosphines and triarylphosphines, as mediators of rhodium-catalyzed propene and hexene hydroformylation reactions

• Ligand for PC bond cleavage during Heck vinylation of aryl halides with Bu acrylate in presence of palladium catalyst compounds

Dicyclohexyl(2-methylphenyl)phosphine [PCy₂(o-Tol)] may be used along with [IrCl(cod)]₂ to form a complex that can catalyze the addition of aliphatic acid chlorides to terminal alkynes to form (Z)-β-chloro-α,β-unsaturated ketones.[2]

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335,H413
• pcodes: P273 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves