tris(2-methylphenyl)phosphane

• ChemBase ID: 70200
• Molecular Formular: C21H21P
• Molecular Mass: 304.365201
• Monoisotopic Mass: 304.1380873
• SMILES: P(c1c(cccc1)C)(c1c(cccc1)C)c1c(cccc1)C
• Canonical SMILES: Cc1ccccc1P(c1ccccc1C)c1ccccc1C
• InChI: InChI=1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3
• InChIKey: COIOYMYWGDAQPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(2-methylphenyl)phosphane
• IUPAC Traditional name: tris(2-methylphenyl)phosphane
• Synonyms: Tri(o-tolyl)phosphine; tri(2-methylphenyl)phosphine; P(o-tol)3; Tri(o-tolyl)phosphine; Tris(o-tolyl)phosphine; Tris(2-methylphenyl)phosphine; tris(2-methylphenyl)phosphane; Tris(2-methylphenyl)phosphine; 三(2-甲苯基)膦; 三(邻甲基苯基)膦; 三(邻甲苯)膦

Database IDs

• CAS Number: 6163-58-2
• EC Number: 228-193-9
• MDL Number: MFCD00008514
• Beilstein Number: 661212
• PubChem SID: 162035923; 24889878; 24857295
• PubChem CID: 80271

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.5082
• LogD (pH = 7.4): 6.5082
• Log P: 6.5082
• Molar Refractivity: 96.7465 cm^3
• Polarizability: 37.639748 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 122-127°C; 123-125 °C; 123-125 °C(lit.); 124-126°C; 128 - 129°C
• Hydrophobicity(logP): 7.182
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; Heck Reaction; Negishi Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (GC); 95%; 95+%; 97%; 98%; 98+%
• Grade: purum
• Linear Formula: (CH3C6H4)3P
• Catalyst for: Silylations

DETAILS

Sigma Aldrich - 287822

Application
Ligand used in a ruthenium-catalyzed direct amination of alcohols.1
Packaging
1, 10 g in glass bottle

REFERENCES

• Preferred phosphine ligand for use in combination with Pd salts in the Heck-type coupling reactions of vinylic halides. For examples, see Palladium(II) acetate, 10516. For a review of the Heck reaction, see: Org. React., 27, 345 (1982).
• The Pd-catalyzed amination of bromoarenes with 1-Boc-piperazine, L13363, in the presence of this ligand, provides a route to arylpiperazines of potential pharmacological interest: Tetrahedron Lett., 39, 2219 (1998).