36282-26-5

Basic information

• Product Name: 2-Bromo-4-fluorobenzonitrile
• Synonyms: 2-BROMO-4-FLUOROBENZONITRILE;2-Bromo-4-fluorobenzonitrile 98%;2-Bromo-4-fluorobenzonitrile98%;Benzonitrile, 2-broMo-4-fluoro-;Bromo-4-fluorobenzonitrile
• CAS NO: 36282-26-5
• Molecular Formula: C₇H₃BrFN
• Molecular Weight: 200.01
• EINECS: 252-949-7
• Product Categories: Fluorobenzene;Aromatic Nitriles;Nitrile;Bromine Compounds;Fluorine Compounds;Nitriles;Aryl Fluorinated Building Blocks;Building Blocks;C7;Chemical Synthesis;Fluorinated Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 36282-26-5.mol

Chemical Properties

• Melting Point: 77-78°C
• Boiling Point: 262.4 °C at 760 mmHg
• Flash Point: 112.5 °C
• Appearance: White powder
• Density: 1.69 g/cm³
• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 1940597
• CAS DataBase Reference: 2-Bromo-4-fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-fluorobenzonitrile(36282-26-5)
• EPA Substance Registry System: 2-Bromo-4-fluorobenzonitrile(36282-26-5)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-36/37/39-36/37-26-9
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 36282-26-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to light yellow powder

InChI:InChI=1/C7H3BrFN/c8-7-3-6(9)2-1-5(7)4-10/h1-3H

Upstream product

• 1006-41-3 2-bromo-4-fluorobenzoic acid 
• 1194-02-1 4-fluorobenzonitrile 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 1309606-40-3 2-bromo-4-fluorobenzaldehyde oxime 
• 1006-40-2 2-bromo-4-fluorobenzamide 

Downstream Products

• 36282-27-6 2'-Brom-4'-fluor-2-phenylacetophenon 
• 1009036-33-2 2-(1-cyano-2-ethoxy-vinyl)-4-fluoro-benzonitrile 
• 53312-82-6 4-amino-2-bromobenzonitrile 
• 946388-45-0 4-(8-azabicyclo[3.2.1]octan-8-yl)-2-bromobenzonitrile 
• 946388-46-1 2-benzyl-4-(8-azabicyclo[3.2.1]octan-8-yl)benzonitrile 
• 946388-47-2 (2-benzyl-4-(8-azabicyclo[3.2.1]octan-8-yl)phenyl)methanamine 
• 946388-31-4 1-(2-benzyl-4-(8-azabicyclo[3.2.1]octan-8-yl)benzyl)-3-(1H-indazol-4-yl)urea 
• 36282-35-6 2-bromo-4,α,α,α',α'-pentafluorobibenzyl 
• 61547-76-0 5-Fluoro-2-(1,1,2,2-tetrafluoro-2-phenyl-ethyl)-benzylamine 
• 61547-74-8 5-Fluoro-2-(1,1,2,2-tetrafluoro-2-phenyl-ethyl)-benzonitrile 
• 463335-96-8 4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-benzonitrile 
• 870562-81-5 4-fluoro-2-(2-oxooxazolidin-3-yl)benzonitrile 
• 870562-75-7 4-fluoro-2-(2-oxopyrrolidin-1-yl)benzonitrile 
• 263845-82-5 2-bromo-4-hydrazinylbenzonitrile 

Relevant articles and documents

Visible-light-driven catalytic oxidation of aldehydes and alcohols to nitriles by 4-acetamido-tempo using ammonium carbamate as a nitrogen source

A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The reaction is performed using ammonium carbamate as the nitrogen source. The practicality of the method is increased by the extension of the dual catalytic system to one-pot two-step conversion of alcohols to nitriles.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles

A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.

A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates

A convenient radical cyclization cascade procedure for the construction of sulfonated indenones from 2-alkynylbenzonitriles and sodium arylsulfinates has been explored under mild reaction conditions. The present methodology offers a low-cost and operationally straightforward approach to synthesizing various sulfonated indenones in moderate to good yields by simple use of cheap sodium persulfate as an oxidant and environmentally benign water as a co-solvent.

Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation

A palladium-catalyzed aminopalladation reaction followed by nucleophilic addition with aldehydes and dehydration is described. This direct and operationally simple procedure provides a rapid and reliable approach to a wide range of functionalized tetrahydroisoquinolines with high selectivity. Mechanistic studies disclosed that the nucleophilic addition, performed via a highly ordered transition-state, is the turnover-limiting step in which the inherent β-hydride elimination of the key Csp3?Pd species was controlled by the confined conformation and the nucleophilicity of the Csp3?Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.

Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library

A Heck cyclisation approach is described for the rapid synthesis of a library of natural product-like small molecules, based on the phenanthridine core. The synthesis of a range of substituted benzylamine building blocks and their incorporation into the library is reported, together with a highly selective cis-dihydroxylation protocol that enables access to the target compounds in an efficient manner. Biological evaluation of the library using zebrafish phenotyping has led to the discovery of compound 20c, a novel inhibitor of early-stage zebrafish embryo development.

Tetrafluorophenethylaralkylamine compounds

New fluoro derivatives of aralkylamine compounds, particularly 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine, as well as the N-alkyl and the N,N-dialkyl derivatives thereof are prepared by reaction of 2-bromobenzonitrile with benzylmagnesium chloride to produce 2'-bromo-2-phenylacetophenone; oxidation of said acetophenone with selenous acid to produce 2-bromobenzil; conversion of the benzil compound by treatment with sulfur tetrafluoride to the corresponding 2-bromo-α ,α-α',α'-tetrafluorobibenzyl; followed by reaction of the 2-bromobibenzyl compound with a metal cyanide to produce the corresponding 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzonitrile. This nitrile compound is then reduced with lithium aluminum hydride to produce the corresponding benzylamine, which is then converted, if desired, to the N-alkyl and/or N,N-dialkyl 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine. Alternatively, the nitrile or the precursor bromobibenzyl can be converted by Grignard reactions to the corresponding α-alkyl or α,α-dialkylbenzylamine which can then be converted if desired to the corresponding N-alkyl and/or N,N-dialkyl substituted benzylamine compound. The phenyltetrafluoroethylbenzylamine as well as its N-alkyl and N,N-dialkyl derivatives are active as antiarrhythmic agents.