Description

Tris(pentafluorophenyl)phosphine (CAS No. 1259-35-4) is a highly specialized organophosphorus compound with the molecular formula C₁₈F₁₅P. This electron-deficient phosphine derivative features three pentafluorophenyl groups bonded to a central phosphorus atom, making it an excellent ligand for transition metal catalysis. Its unique steric and electronic properties enhance reactivity in cross-coupling reactions, hydrofunctionalizations, and other catalytic processes. With exceptional thermal stability and solubility in organic solvents, it is widely used in academic and industrial research. Packaged under inert gas to ensure purity and longevity, this reagent is ideal for advanced synthetic applications.

Properties

• CAS Number: 1259-35-4
• Complexity: 566
• IUPAC Name: tris(2,3,4,5,6-pentafluorophenyl)phosphane
• InChI: InChI=1S/C18F15P/c19-1-4(22)10(28)16(11(29)5(1)23)34(17-12(30)6(24)2(20)7(25)13(17)31)18-14(32)8(26)3(21)9(27)15(18)33
• InChI Key: FQLSDFNKTNBQLC-UHFFFAOYSA-N
• Exact Mass: 531.9498094
• Molecular Formula: C18F15P
• Molecular Weight: 532.1
• SMILES: C1(=C(C(=C(C(=C1F)F)P(C2=C(C(=C(C(=C2F)F)F)F)F)C3=C(C(=C(C(=C3F)F)F)F)F)F)F)F
• Monoisotopic Mass: 531.9498094
• Synonyms: Tris(pentafluorophenyl)phosphine, 1259-35-4, Phosphine, tris(pentafluorophenyl)-, EINECS 215-021-2, DTXSID70154988, MLO 74-62, TPFPP, DTXCID6077479, 215-021-2, fqlsdfnktnbqlc-uhfffaoysa-n, Tris(perfluorophenyl)phosphine, tris(2,3,4,5,6-pentafluorophenyl)phosphane, Phosphine, tris(2,3,4,5,6-pentafluorophenyl)-, MFCD00079654, R4P6L83YFZ, Tris(2,3,4,5,6-pentafluorophenyl)phosphine, C18F15P, UNII-R4P6L83YFZ, SCHEMBL168040, BCP22560, AKOS015853251, Tris(pentafluorophenyl)phosphine, 97%, CS-W009612, HY-W008896, AS-66527, SY009849, DB-010730, NS00044977, ST51006801, T2484, D70445, Tris(2,3,4,5,6-pentafluorophenyl)phosphine #

Application

Tris(pentafluorophenyl)phosphine is a versatile ligand in palladium- and nickel-catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Heck couplings. Its strong electron-withdrawing properties facilitate oxidative addition steps in catalytic cycles. Researchers also employ it in hydroamination and hydroarylation reactions due to its ability to stabilize low-valent metal centers. Additionally, it serves as a precursor for generating highly reactive phosphonium salts in organic synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.9%): 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 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.9%)

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