403-54-3

Basic information

• Product Name: 3-Fluorobenzonitrile
• Synonyms: 1-Cyano-3-fluorobenzene;1-Fluoro-3-cyanobenzene;3-Fluorobenzonitrile, 98% 10GR;3-Fluorobenzonitrile, 97+%;Between fluorine benzene nitriles;Inter-fluorobenzonitrile;Benzonitrile, 3-fluoro-;M-FLUOROBENZONITRILE
• CAS NO: 403-54-3
• Molecular Formula: C₇H₄FN
• Molecular Weight: 121.11
• EINECS: 206-963-5
• Product Categories: Fluorobenzene;Nitrile;Fluorine Compounds;Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;cyanide| alkyl Fluorine;FINE Chemical & INTERMEDIATES;Boron, Nitrile, Thio,& TM-Cpds;Aromatic Nitriles
• Mol File: 403-54-3.mol
• Article Data: 64

Chemical Properties

• Melting Point: −16 °C(lit.)
• Boiling Point: 182-183 °C753 mm Hg(lit.)
• Flash Point: 154 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.133 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000903mmHg at 25°C
• Refractive Index: n20/D 1.5043(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1858941
• CAS DataBase Reference: 3-Fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorobenzonitrile(403-54-3)
• EPA Substance Registry System: 3-Fluorobenzonitrile(403-54-3)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-39-36/37/39-36
• RIDADR: UN 3276 6.1/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 403-54-3(Hazardous Substances Data)

Usage

Description

3-Fluorobenzonitrile is an organic compound with the chemical formula C7H4FN. It is a clear colorless to yellow liquid that has been studied for its microwave spectrum and chemical properties. 3-Fluorobenzonitrile has been investigated for its amination reactions with various amines, such as morpholine, in dimethyl sulfoxide (DMSO) at elevated temperatures.

Uses

Used in Chemical Synthesis:
3-Fluorobenzonitrile is used as a synthetic building block for the preparation of various organic compounds, including bis(3-cyanophenoxy)phenylenes. These compounds have potential applications in the development of advanced materials and chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-fluorobenzonitrile can be used as a starting material for the synthesis of various drug candidates. Its unique chemical properties, such as the presence of a fluorine atom and a nitrile group, make it a valuable intermediate for the development of new medications.
Used in Material Science:
3-Fluorobenzonitrile can also be utilized in the field of material science for the development of novel materials with specific properties. The introduction of a fluorine atom can significantly alter the physical and chemical characteristics of the resulting compounds, making them suitable for various applications, such as in electronics or as specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, 3-fluorobenzonitrile is a valuable compound for research and development purposes. It can be used in the study of various chemical reactions, such as amination, and can provide insights into the reactivity and behavior of similar compounds. This knowledge can be applied to the design and synthesis of new molecules with specific properties and applications.

Synthesis

Many of the advances made in the Halex reaction have been applied to fluorodenitration reactions, for example, 3-nitrobenzonitrile reacts with KF and catalytic amounts of Ph4PBr to give 3-fluorobenzonitrile.

InChI:InChI=1/C9H6F3NO2/c10-9(11,12)15-6-1-2-7-5(3-6)4-8(14)13-7/h1-3H,4H2,(H,13,14)

Upstream product

• 372-19-0 meta-fluoroaniline 
• 462-06-6 fluorobenzene 
• 460-19-5 ethanedinitrile 
• 100-47-0 benzonitrile 
• 76-05-1 trifluoroacetic acid 
• 85369-62-6 K{18-crown-6}{closo-3-(triphenylphosphine)-3-(eta.2-C(m-FC₆H₄)NOC(O)-)-3,1,2-RhC₂B₉H₁₁} 
• 557-21-1 zinc(II) cyanide 
• 100-82-3 (3-fluorophenyl)methanamine 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 658-28-6 (3-fluorophenyl)(methyl)sulfide 
• 455-37-8 3-fluorobenzamide 
• 24964-64-5 3-Cyanobenzaldehyde 
• 75-05-8 acetonitrile 
• 456-47-3 3-fluoro-benzenemethanol 

Downstream Products

• 133118-49-7 3-fluorobenzenecarboximidic acid methyl ester hydrochloride 
• 92083-22-2 3-(2,3-dihydro-1H-indol-1-yl)benzonitrile 
• 92083-25-5 3-(5-chloro-1-indolinyl)benzonitrile 
• 75207-72-6 3-fluorobenzenecarboximidamide hydrochloride 
• 69491-64-1 3-fluorobenzimidamide 
• 40281-50-3 1-(3-fluorophenyl)-2-phenylethan-1-one 
• 187088-51-3 1.2-bis-(3-cyanophenoxy)-benzene 
• 14378-89-3 3-(diphenylphosphanyl)benzonitrile 
• 175696-74-9 3-(piperidin-1-yl)benzonitrile 
• 204078-31-9 3-(morpholin-4-yl)benzonitrile 
• 204078-35-3 3-(4-methylpiperazin-1-yl)benzonitrile 
• 287389-06-4 3-(9H-carbazol-2-yloxy)-benzonitrile 
• 775252-53-4 3-Fluoro-benzimidic acid methyl ester 
• 25699-85-8 3-(1-imidazolyl)benzonitrile 

Relevant articles and documents

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation

Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.

Method for catalyzing oxidation of amines to generate nitrile by using nonmetal mesoporous nitrogen-doped carbon material

The invention discloses a method for preparing nitrile by catalyzing amine oxidation with a non-metal mesoporous nitrogen-doped carbon material catalyst, which is applied to the field of synthesis, the material is prepared by using a nitrogen-containing organic ligand as a precursor and silica sol as a template agent, calcining in the atmosphere of inert gases such as N2 or Ar and then removing the template agent; oxygen or air is used as an oxygen source, the reaction is performed at 80-130 DEG C under the action of ammonia water in the presence of a solvent, the effect is good, and the product still keeps higher activity after being recycled for more than 8 times, and has a wide industrial application prospect. The invention provides a heterogeneous non-metal catalytic system for catalyzing amine oxidation to prepare nitrile for the first time, and compared with a reported metal catalyst, the heterogeneous non-metal catalytic system does not bring metal pollution to a product to influence the effect of cyano drugs.