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Merck
CN

651885

Sigma-Aldrich

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
MDL number:
MFCD08276773
UNSPSC Code:
12352002
PubChem Substance ID:
24883863

Key Documents

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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

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.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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