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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.
In the Vinony graph
Within Vinony's link graph, triphenylphosphine is referenced by 249 other articles, and connects out to haloalkane, phosphonium cation and lithium.
Vinony files it under Chembox having GHS data, ECHA InfoCard ID from Wikidata and Phenyl compounds.
Its subject is documented across 24 Wikipedia language editions.
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.