Tri(o-tolyl)phosphine, 98+%, Thermo Scientific Chemicals
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Tri(o-tolyl)phosphine, 98+%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Tri(o-tolyl)phosphine, 98+%, Thermo Scientific Chemicals

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Catalog number A12093.03
also known as A12093-03
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Chemical Identifiers
CAS6163-58-2
IUPAC Nametris(2-methylphenyl)phosphane
Molecular FormulaC21H21P
InChI KeyCOIOYMYWGDAQPM-UHFFFAOYSA-N
SMILESCC1=CC=CC=C1P(C1=CC=CC=C1C)C1=CC=CC=C1C
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SpecificationsSpecification SheetSpecification Sheet
FormCrystals or powder or crystalline powder
Melting Point (clear melt)122.0-129.0?C
Identification (FTIR)Conforms
Appearance (Color)White
Assay (GC)≥98.0%
Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.

Solubility
Soluble in alcohol. Slightly soluble in cold water. Insoluble in water.

Notes
Light sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only

General References:

  1. 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).
  2. 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).
  3. Chang, C. H.; Chen, M. H.; Du, W. S.; Gliniak, J.; Lin, J. H.; Wu, H. H.; Chan, H. F.; Yu, J. S. K.; Wu, T. K. A Ruthenium-Based Biomimetic Hydrogen Cluster for Efficient Photocatalytic Hydrogen Generation from Formic Acid. Chem. Eur. J. 2015, 21 (17), 6617-6622.
  4. Lennartson, A.; Håkansson, M. A missing link between chiral four-and five-coordinate complexes. New J. Chem. 2015, 39 (5), 3353-3356.