241154-09-6

Basic information

• Product Name: 2,3,5-TRIFLUOROBENZONITRILE
• Synonyms: 2,3,5-TRIFLUOROBENZONITRILE;3,5-Trifluorobenzonitrile
• CAS NO: 241154-09-6
• Molecular Formula: C₇H₂F₃N
• Molecular Weight: 157.09
• Product Categories: Aromatic Nitriles;Nitrile;Fluorine series
• Mol File: 241154-09-6.mol

Chemical Properties

• Boiling Point: 170.7°Cat760mmHg
• Flash Point: 57°C
• Appearance: /
• Density: 1.36
• Vapor Pressure: 1.45mmHg at 25°C
• Refractive Index: 1.4700
• CAS DataBase Reference: 2,3,5-TRIFLUOROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-TRIFLUOROBENZONITRILE(241154-09-6)
• EPA Substance Registry System: 2,3,5-TRIFLUOROBENZONITRILE(241154-09-6)

Safety Data

• Hazard Codes: T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36-36/37-23-9
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 241154-09-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,5-Trifluorobenzonitrile is used as a key intermediate in the production of a variety of chemicals. Its unique structure, featuring three fluorine atoms, makes it a valuable component in the synthesis of complex organic molecules, particularly those with fluorinated functional groups.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2,3,5-Trifluorobenzonitrile is utilized as a building block for the development of new drugs. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the resulting compounds, potentially enhancing their therapeutic efficacy and selectivity.
Used in Agricultural Industry:
2,3,5-Trifluorobenzonitrile is employed as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can improve their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and agricultural productivity.
Used in Industrial Chemicals Production:
2,3,5-TRIFLUOROBENZONITRILE also finds application in the production of various industrial chemicals, where its unique properties can be harnessed to create novel materials with specific characteristics, such as enhanced stability, reactivity, or selectivity in chemical processes.
Safety and Handling:
Given its classification as a hazardous substance, 2,3,5-Trifluorobenzonitrile poses potential risks to the environment and human health. It is crucial to handle and dispose of this compound with care, adhering to proper safety protocols and regulations to minimize its impact on both people and the environment.

InChI:InChI=1/C7H2F3N/c8-5-1-4(3-11)7(10)6(9)2-5/h1-2H

Upstream product

• 773-82-0 Pentafluorobenzonitrile 
• 16582-93-7 C₇HF₄N^(1-) 

Downstream Products

• 507240-02-0 3,5-difluoro-2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-ylmethoxy)-benzonitrile 

Relevant articles and documents

Hydrodefluorination of functionalized fluoroaromatics with triethylphosphine: A theoretical and experimental study

Recently we reported the metal free hydrodefluorination of selected fluoroaromatics using triethylphosphine as the sole defluorinating agent. That prompted us to evaluate the mechanistic proposal and in the light of these results, along with new experimental evidence, we have now modified the initial proposal. The new mechanism avoids the highly energetic β-elimination step of roughly 71 kcal mol-1 for hexafluorobenzene and pentafluoropyridine at 393.15 K, invoking the participation of water. The use of D2O confirmed the role of water as the hydrogen source, yielding the corresponding deutero-defluorinated products; DFT calculations agree with this new proposed mechanism. We also report herein the use of this one-pot hydrodefluorination method applied to a broader number of fluoroaromatic derivatives; some of them allowed the collection of key mechanistic evidence.

Reductive dehalogenation of polyfluoroarenes by zinc in aqueous ammonia

Aqueous ammonia has been found to be a good and versatile medium for the highly selective hydrodehalogenation of polyfluoroarenes by zinc under unprecedentedly mild conditions. The reduction of pentafluorobenzoic acid, 2,3,4,5,6-pentafluorobenzyl alcohol, pentafluorobenzamide, pentafluoropyridine, heptafluoro-2-naphthoic acid, 1,3,4,5,7,8-hexafluoro-2-naphthoic acid, octafluoronaphthalene, octafluorotoluene, decafluorobiphenyl, chloropentafluorobenzene and 4-chlorotetrafluorobenzoic acid give products derived from the removal of one or two halogen atoms. A reduction mechanism, proceeding through electron capture to give a radical anion and then fragmentation of the latter, has been suggested. The observed high selectivity of the process suggests a radical anion formed by direct electron transfer from zinc to substrate. The dehalogenation regioselectivity is basically in accordance with that expected for radical anion fragmentation.

Aromatic radical-anions. XII. A cyclic amperometric and ESR study of the transformations of polyfluorinated benzonitrile radical-anions

Cyclic voltamperometry and ESR spectrometry were used to study the chemical transformations of radical-anions of benzonitrile derivatives containing from two to five fluorine atoms.Two types of transformations were found to be characteristic for such species, namely, the elimination of a fluoride anion and subsequent formation of defluorination products and dimerization with the subsequent formation of fluorinated derivatives of 4,4'-dicyanodiphenyl.The facility of these processes depends significantly on the number and arrangement of the fluorine atoms in the benzene ring.The relationship between the electronic structure and reactivity of fluorinated benzonitrile radical-anions was examined.