Pentafluorobenzonitrile

• CAS: 773-82-0
• Catalog Number: ACM773820
• Category: Main Products
• Molecular Weight: 193.07
• Molecular Formula: C7F5N
• Synonyms: 2,3,4,5,6-Pentafluorobenzonitrile;; Perfluorobenzonitrile
• Boiling Point: 162-164 °C
• Melting Point: 2.4 °C
• Flash Point: 29 °C
• Density: 1.532 g/mL at 25 °C
• Appearance: Colorless to Light Yellow Liquid

Case Study

Pentafluorobenzonitrile as an Electrophilic Building Block for Polyfluorinated Oxacalixarenes

Kovtonyuk, Vladimir N., et al. Journal of Fluorine Chemistry 222 (2019): 59-67.

Pentafluorobenzonitrile serves as a versatile electrophilic component in the synthesis of polyfluorinated tetraoxacalix[4]arenes and bicyclooxacalixarenes via sequential nucleophilic aromatic substitution with resorcinol, orcinol, and tetrafluororesorcinol, enabling macrocyclic hosts with metal-complexing ability.
Fabrication Process: Pentafluorobenzonitrile was reacted with resorcinol or orcinol in Et3N-CH3CN (0 °C to room temperature) to give triphenyl ethers 1a/2a. These were further treated with resorcinol, orcinol, or tetrafluororesorcinol under reflux to form tetraoxacalixarenes 3a-6a (ABAB or ABAC type). Prolonged heating with additional tetrafluororesorcinol or orcinol yielded bicyclooxacalixarenes.
Performance Evaluation: 19F NMR showed characteristic shifts for inner-cavity and outer-rim fluorine atoms. X-ray structure of 4a revealed dihedral angles between fluorinated benzonitrile rings of 41.9° and 86.3°. Bicyclooxacalixarene 7 crystallized with three benzene molecules in a layered packing. ESI-MS demonstrated that 5a and 8 form complexes with Ni^Ⅱ and Ag^Ⅰ, respectively (e.g., [M8 + Ag + CH3OH]⁺ at m/z 777). No complexes were detected for 7 with Ni^Ⅱ.
Conclusion: Pentafluorobenzonitrile is a key precursor to fluorinated calixarenes with tunable cavity structures and cation-binding properties.

Pentafluorobenzonitrile as a Tetrafunctional Monomer for Soluble, Porous Ladder Polymers

Ranganathan, Krishnan, et al. Polymer 135 (2018): 295-304.

Pentafluorobenzonitrile (PFBN) serves as a versatile tetrafunctional building block for synthesizing semi-fluorinated poly(arylene ether) ladder polymers via sequential nucleophilic aromatic substitution with bisphenols, yielding soluble, microporous materials with tunable surface area.
Fabrication Process: PFBN was first reacted with bisphenols (hydroquinone, bisphenol-A, or 6F-BPA) or Na2S in a 2:1 molar ratio in DMF at room temperature to give tetrafunctional derivatives 1a-d. These were then polymerized with a second bisphenol (1:2 ratio) in DMF at 50-60 °C for 24 h. Polymers were precipitated in acidified water and purified by reprecipitation from THF into methanol.
Performance Evaluation: 19F NMR confirmed selective substitution at the para-position (loss of -141.8 ppm signal), while ortho-fluorines (-150 ppm) remained available for subsequent polymerization. MALDI-TOF MS of the 1a/bisphenol-A copolymer showed a repeating unit mass of 756.8 Da, corresponding to one tetrafunctional unit plus two bisphenol-A units minus 4HF, confirming the ladder structure. GPC gave Mn up to 62,400 Da. BET analysis revealed surface areas up to 455 m²/g (pore volume 0.62 cm³/g) depending on monomer combination.
Conclusion: PFBN enables mild-condition synthesis of soluble ladder polymers with intrinsic microporosity, suitable for gas separation or membrane applications.

Pentafluorobenzonitrile as a Ligand Precursor for Half-Sandwich Iridium(III) Complexes via C-F Activation

Mak, Kar Hang Garvin, et al. Journal of Organometallic Chemistry 741 (2013): 176-180.

Pentafluorobenzonitrile (C6F5CN) acts as a versatile substrate for C-F bond activation by Cp*Ir(CO)2 (1), leading to a family of half-sandwich iridium complexes under mild, base-assisted conditions, with the perfluoroaryl ligand exhibiting restricted rotation.
Experimental Protocol: Complex 1 was stirred with neat or excess C6F5CN in the presence of NaOH pellets or basic alumina, giving the diaryl complex Cp*Ir(CO)(p-C6F4CN)2 (4). Under aqueous conditions, 1 afforded the metallacarboxylic acid 2, which decarboxylated with base to the hydride 5. In halogenated solvents, 5 underwent hydride-halogen exchange to the chloro (6a) or iodo (6b) derivatives. In air/water, 1 gave the hemiaminal complex 7a along with C6F5CONH2.
Performance Evaluation: X-ray structures confirmed 4 (Ir-C(aryl) 2.068 Å) and 6b (Ir-I 2.6967 Å). 19F NMR of 6a showed coalescence of ortho-F signals at 273 K (ΔG‡ = 48 kJ/mol, δν = 1915 Hz at 213 K), indicating restricted rotation of the p-C6F4CN ring. The diaryl complex 4 showed IR ν(CO) at 2045 cm^-1. Reactions proceeded via an anionic intermediate [Cp*Ir(CO)(p-C6F4CN)]-.
Conclusion: Pentafluorobenzonitrile serves as a reactive source of the p-C6F4CN ligand in iridium-mediated C-F activation, enabling access to structurally diverse organometallic species with dynamic stereochemistry.

Custom Q&A

What is the molecular formula of pentafluorobenzonitrile?

The molecular formula of pentafluorobenzonitrile is C7F5N.

What are the synonyms of pentafluorobenzonitrile?

The synonyms of pentafluorobenzonitrile are 773-82-0, 2,3,4,5,6-Pentafluorobenzonitrile, Benzonitrile, pentafluoro-, and Perfluorobenzonitrile.

What is the molecular weight of pentafluorobenzonitrile?

The molecular weight of pentafluorobenzonitrile is 193.07 g/mol.

When was pentafluorobenzonitrile created?

Pentafluorobenzonitrile was created on March 26, 2005.

When was pentafluorobenzonitrile last modified?

Pentafluorobenzonitrile was last modified on October 21, 2023.

What is the IUPAC name of pentafluorobenzonitrile?

The IUPAC name of pentafluorobenzonitrile is 2,3,4,5,6-pentafluorobenzonitrile.

What is the InChIKey of pentafluorobenzonitrile?

The InChIKey of pentafluorobenzonitrile is YXWJGZQOGXGSSC-UHFFFAOYSA-N.

What is the CAS number of pentafluorobenzonitrile?

The CAS number of pentafluorobenzonitrile is 773-82-0.

What is the European Community (EC) number of pentafluorobenzonitrile?

The European Community (EC) number of pentafluorobenzonitrile is 212-259-9.

What is the topological polar surface area of pentafluorobenzonitrile?

The topological polar surface area of pentafluorobenzonitrile is 23.8 Ų.