Description

Bis(pentafluorophenyl)phenylphosphine (CAS No. 5074-71-5) is a highly specialized organophosphorus compound with the molecular formula C₁₈H₅F₁₀P. This fluorinated phosphine derivative, also known by its IUPAC name bis(2,3,4,5,6-pentafluorophenyl)-phenylphosphane, features two electron-withdrawing pentafluorophenyl groups and a phenyl group bonded to a central phosphorus atom. Its unique electronic and steric properties make it an exceptional ligand for transition metal catalysis, particularly in reactions requiring air- and moisture-sensitive conditions. With exceptional purity standards (typically ≥95% by GC or HPLC), this compound is rigorously tested for trace metals and moisture content to ensure optimal performance in demanding synthetic applications. Packaged under inert gas in amber glass vials to prevent degradation, it is an essential reagent for researchers in organometallic chemistry, materials science, and pharmaceutical development.

Properties

• CAS Number: 5074-71-5
• Complexity: 479
• IUPAC Name: bis(2,3,4,5,6-pentafluorophenyl)-phenyl-phosphane
• InChI: InChI=1S/C18H5F10P/c19-7-9(21)13(25)17(14(26)10(7)22)29(6-4-2-1-3-5-6)18-15(27)11(23)8(20)12(24)16(18)28/h1-5H
• InChI Key: OYNXPGGNQMSMTR-UHFFFAOYSA-N
• Exact Mass: 441.99691878
• Molecular Formula: C18H5F10P
• Molecular Weight: 442.2
• SMILES: C1=CC=C(C=C1)P(C2=C(C(=C(C(=C2F)F)F)F)F)C3=C(C(=C(C(=C3F)F)F)F)F
• Monoisotopic Mass: 441.99691878
• Physical Description: White powder;
• Synonyms: Bis(pentafluorophenyl)phenylphosphine, 5074-71-5, Decafluorotriphenylphosphine, DFTPP, EINECS 225-780-1, Bis(pentafluorophenyl) phenyl phosphite, DTXSID90198783, DTXCID50121274, 225-780-1, SpectraSynQ 443, bis(2,3,4,5,6-pentafluorophenyl)-phenylphosphane, Bis(perfluorophenyl)(phenyl)phosphine, Decafluorotriphenylphosphine (DFTPP) SV Tuning 1000 microg/mL in Acetone, Decafluorotriphenylphosphine (DFTPP) SV Tuning 2500 microg/mL in Acetone, C18H5F10P, Ultramark 443, MFCD00000291, Phosphine, bis(pentafluorophenyl)phenyl-, decafluorotriph-enylphosphine, SCHEMBL476825, BIS(2,3,4,5,6-PENTAFLUOROPHENYL)(PHENYL)PHOSPHANE, Bis(pentafluorophenyl)phenyl phosphine, AKOS008901268, AS-63164, DB-051837, B4560, CS-0085851, T70977, Decafluorotriphenylphosphine, analytical standard, Bis(2,3,4,5,6-pentafluorophenyl)(phenyl)phosphine #, Decafluorotriphenylphosphine 1000 microg/mL in Acetone, Bis(pentafluorophenyl)phenylphosphine, analytical standard, for mass spectrometry, Decafluorotriphenylphosphine; di(2:3:4:5:6-pentafluorophenyl)(phenyl)phosphine; Di(2,3,4,5,6-pentafluorophenyl)(phenyl)phosphine

Application

Bis(pentafluorophenyl)phenylphosphine serves as a privileged ligand in palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura, Heck) due to its strong σ-donor/π-acceptor properties. Its electron-deficient fluorinated aryl groups enhance oxidative addition kinetics in metal complexes while improving catalyst stability. The compound is also employed in the synthesis of luminescent materials and as a precursor for phosphorus-containing polymers with high thermal stability. Researchers utilize it to modulate steric and electronic environments in homogeneous catalysis.

Safety and Hazards

GHS Hazard Statements

• H315 (93.6%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (93.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (91.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (93.6%)
• Eye Irrit. 2 (93.6%)
• STOT SE 3 (91.5%)

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