tris(2-fluorophenyl)phosphane

• CAS: 84350-73-2
• Catalog Number: ACM84350732
• Category: Main Products
• Molecular Weight: 316.25
• Molecular Formula: C18H12F3P
• Synonyms: Tris(2-fluorophenyl)phosphine
• Appearance: White to Light Yellow solid

Case Study

Tris(2-fluorophenyl)phosphine as an Electrophilic Phosphine Ligand for Template Synthesis of Benzannulated Triphosphamacrocycles

Edwards, Peter G., et al. Dalton Transactions 43.41 (2014): 15646-15655.

Tris(2-fluorophenyl)phosphine serves as a key electrophilic building block in the manganese(I)-templated construction of nine-membered benzannulated triphosphamacrocycles, where its ortho-fluoro substituents act as leaving groups for intramolecular nucleophilic aromatic substitution by coordinated phosphide nucleophiles.
Synthesis and Coordination: The complex fac-[Mn(CO)3(H2PC6H4PH2)(P(2-FC6H4)3)]OTf (5) was prepared by reacting fac-[Mn(CO)3(H2PC6H4PH2)(OTf)] (4) with an excess of tris(2-fluorophenyl)phosphine in dichloromethane under reflux. The facial geometry was confirmed by NMR and single-crystal X-ray diffraction, showing a Mn-P bond length of 2.3749(5) Å for the tris(2-fluorophenyl)phosphine ligand.
Macrocyclisation Performance: Upon dissolution in THF, complex 5 underwent spontaneous partial cyclisation to give the linear tridentate intermediate 6 containing primary, secondary and tertiary phosphine donors. Subsequent treatment with KOtBu induced full ring-closure, affording the macrocyclic complex fac-[Mn(CO)3(tribenzo-9aneP3-H2,PhF)]+ (7). The secondary phosphine groups of 7 could be methylated to give the stable tri-tertiary macrocycle 8 in 65% yield.
Conclusion: Tris(2-fluorophenyl)phosphine provides an electrophilic aryl fluoride motif that enables base-activated P-C bond formation under mild conditions. Its combination with a Mn(CO)3 template offers a versatile route to rigid, benzo-fused triphosphamacrocycles for coordination and supramolecular chemistry.

Tris(2-fluorophenyl)phosphine as a Monodentate Ligand for Rhenium(I) Tricarbonyl Complexes

Edwards, Peter G., et al. Journal of Organometallic Chemistry 696.8 (2011): 1652-1658.

Tris(2-fluorophenyl)phosphine (PArF₃) acts as a moderately π-accepting monodentate phosphine ligand that can displace a labile alcohol donor from a fac-Re(CO)3(κ³-P,N,O) scaffold. However, its weakly coordinating fluorinated aryl groups render the complex susceptible to ligand dissociation upon deprotonation, limiting its use in template-assisted macrocyclisation.
Synthesis and Coordination: The complex fac-[Re(CO) ₃(κ²-P,N-S-PNO)(PArF₃)]BF₄ (5) was prepared by heating fac-[Re(CO) ₃(κ³-S-PNO)]BF₄ (3) with one equivalent of PArF₃ in nitromethane at 80 °C for 30 min. After work-up, 5 was isolated as a colourless solid in 53% yield. The ³¹P{¹H} NMR spectrum showed two doublets at δ -10.4 and -72.3 ppm with ²J_{P-P} = 26.8 Hz, confirming the presence of both the coordinated primary phosphine of S-PNO and the PArF₃ ligand. The IR spectrum displayed ν(CO) bands at 2036, 1955 and 1911 cm^-1.
Reactivity and Limitations: Addition of base (Et ₃N or KOᵗBu) to a suspension of 5 in THF or nitromethane caused immediate loss of PArF₃ from the metal centre, as evidenced by ³¹P NMR spectroscopy. No macrocyclisation via nucleophilic aromatic substitution of the ortho-fluoro groups was observed. The lability of PArF₃ is attributed to its relatively weak donor strength and the steric protection of the rhenium centre.

Custom Q&A

What is the molecular formula of Tris(2-fluorophenyl)phosphine?

The molecular formula is C18H12F3P.

When was the compound created and modified?

It was created on 2007-02-08 and modified on 2023-11-25.

What is the IUPAC name for Tris(2-fluorophenyl)phosphine?

The IUPAC name is tris(2-fluorophenyl)phosphane.

What is the InChIKey for Tris(2-fluorophenyl)phosphine?

The InChIKey is LZTKJXHKOLJIHI-UHFFFAOYSA-N.

How many hydrogen bond acceptors are there in the compound?

There are 3 hydrogen bond acceptors.

What is the exact mass of Tris(2-fluorophenyl)phosphine?

The exact mass is 316.06287187 g/mol.

Is the compound a canonical form?

Yes, the compound is canonicalized.

What is the molecular weight of Tris(2-fluorophenyl)phosphine?

The molecular weight is 316.3 g/mol.

What is the XLogP3-AA value for the compound?

The XLogP3-AA value is 4.9.

How many covalently-bonded units are there in the compound?

There is 1 covalently-bonded unit.

Synthetic Use

Upstream Synthesis Route 1

• 1072-85-1

• 84350-73-2

Reference: [1]Stegmann, H. B.; Kuehne, H.-M.; Wax, G.; Scheffler, K.
[Phosphorus and Sulfur and the Related Elements, 1982, vol. 13, p. 331 - 336]
[2]Goto, Akihiro; Otake, Kazuki; Kubo, Ozora; Sawama, Yoshinari; Maegawa, Tomohiro; Fujioka, Hiromichi
[Chemistry - A European Journal, 2012, vol. 18, # 36, p. 11423 - 11432]