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triphenylphosphine
Sign in to saveTriphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
Chemical data
- Formula
- C18H15P
- Molecular weight
- 262.3 g/mol
- IUPAC name
- triphenylphosphane
- SMILES
- C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
- InChIKey
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N
- XLogP
- 4.6
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 262.091
Show 4 more facts
- Commons category
- Triphenylphosphine
- chemical formula
- C₁₈H₁₅P
- canonical SMILES
- C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
- melting point
- 80.0
via Wikidata · CC0
~8 min read
Encyclopedic overview
17 sectionsContents
- Preparation and structure
- Principal reactions with chalcogens, halogens, and acids
- Oxidation
- Chlorination
- Protonation
- Organic reactions
- Quaternization
- Mitsunobu reaction
- Appel reaction
- Deoxygenation
- Sulfonation
- Reduction to diphenylphosphide
- Transition metal complexes
- Polymer-anchored PPh<sub>3</sub> derivatives
- See also
- References
- External links
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
==Preparation and structure== Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium: PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl
Excerpted from Wikipedia’s “triphenylphosphine” article, available under the CC BY-SA 4.0 licence.