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Merck
CN

651885

Dicyclohexyl(2-methylphenyl)phosphine

95%

Synonym(s):

(o-Tolyl)dicyclohexylphosphine

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About This Item

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

Key Documents

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Product Name

Dicyclohexyl(2-methylphenyl)phosphine, 95%

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

SMILES string

Cc1ccccc1P(C2CCCCC2)C3CCCCC3

InChI key

MKHYBAIPMJGEQO-UHFFFAOYSA-N

assay

95%

form

solid

reaction suitability

reaction type: Cross Couplings

mp

90-93 °C

functional group

phosphine

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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
02923HD

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Iridium-catalyzed addition of aroyl chlorides and aliphatic acid chlorides to terminal alkynes.
Iwai T, et al.
Journal of the American Chemical Society, 134(2), 1268-1274 (2011)
Armarego WLF and Chai CLL
Purification of Laboratory Chemicals, 736-736 (2013)

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