Triphenylphosphine

Other Trading Names:

  • PPh3

CAS Number: 603-35-0

HS Code: 29314990

Types of Packaging:

  • 25kg/bag
  • 25kg/drum
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Triphenylphosphine

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Appearance

White crystalline powder

Purity

99.5%

Assay

≥99.5%

Melting point

79.0 ~ 81.0℃

Residue on ignition

≤0.3%

Loss on drying

≤0.5%

Triphenylphosphine oxide

≤0.5%

Chemical Description:

  • Triphenylphosphine, often abbreviated as PPh3, is an organophosphorus compound with the chemical formula C18H15P.
  • It is composed of a phosphorus atom bonded to three phenyl groups, each of which is a benzene ring.
  • The phosphorus atom in triphenylphosphine has a lone pair of electrons, making it a strong nucleophile and an excellent ligand in coordination chemistry.
  • Triphenylphosphine appears as a white crystalline solid at room temperature and has a characteristic faint odor.
  • The compound has a melting point of approximately 80-82°C (176-180°F) and a boiling point of around 377°C (711°F).
  • It is sparingly soluble in water but readily dissolves in organic solvents such as benzene, toluene, ether, and chloroform.
  • In the context of its electronic structure, triphenylphosphine is often described as having a pyramidal geometry around the phosphorus atom.
  • The three phenyl rings are planar and are arranged in a roughly tetrahedral configuration around the phosphorus center.
  • This geometry allows for significant steric hindrance, making triphenylphosphine bulky compared to simpler phosphine compounds like phosphine (PH3).
  • The lone pair on the phosphorus can be donated to metal centers, forming stable metal-phosphine complexes used in various catalytic processes.
  • Triphenylphosphine is widely utilized in homogeneous catalysis, particularly in processes such as the Heck reaction, Suzuki coupling, and the Stille coupling.
  • It acts as a reducing agent in organic synthesis, often employed in the reduction of alkyl halides and the preparation of ylides for Wittig reactions.
  • The Wittig reaction, in particular, uses triphenylphosphine to generate phosphonium ylides, which react with carbonyl compounds to form alkenes.
  • Triphenylphosphine also finds applications in the synthesis of organophosphorus compounds, including various ligands and catalysts.
  • In polymer chemistry, it can be used to modify the properties of polymers and in the synthesis of flame-retardant materials.
  • Due to its role as a ligand, triphenylphosphine is essential in the preparation of many transition metal complexes that serve as catalysts in industrial and laboratory-scale chemical reactions.
  • Safety considerations include its moderate toxicity and potential to cause skin irritation; therefore, proper handling and protective measures are recommended.
  • Triphenylphosphine should be stored in a cool, dry place, away from moisture and oxidizing agents to maintain its stability and prevent degradation.
  • Its reactivity with strong oxidizers can lead to the formation of triphenylphosphine oxide (OPPh3), a common by-product in reactions involving triphenylphosphine.
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Triphenylphosphine