125418-95-3

Basic information

• Product Name: 2-(4-bromo-2-formylphenoxy)acetonitrile
• Synonyms: 2-(4-bromo-2-formylphenoxy)acetonitrile
• CAS NO: 125418-95-3
• Molecular Weight: 240.056
• Mol File: 125418-95-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-(4-bromo-2-formylphenoxy)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromo-2-formylphenoxy)acetonitrile(125418-95-3)
• EPA Substance Registry System: 2-(4-bromo-2-formylphenoxy)acetonitrile(125418-95-3)

Safety Data

• Hazardous Substances Data: 125418-95-3(Hazardous Substances Data)

Usage

Type of compound

Nitrile derivative

Elements present

Carbon (C), Hydrogen (H), Bromine (Br), Nitrogen (N), and Oxygen (O)

Contains

A bromine atom, a formyl group (-CHO), and a phenoxy group (-O-C6H4-)

Common uses

Building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals

Potential applications

Materials science and other research fields

Property dependence

Precise properties and potential uses would likely depend on its specific chemical context and the reactions in which it is involved.

Upstream product

• 107-14-2 chloroacetonitrile 
• 1761-61-1 5-bromosalicyclaldehyde 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 79205-32-6 3-amino-6-bromo-4H-chromen-4-one 
• 52789-91-0 (5-bromobenzofuran-2-yl)(p-tolyl)methanone 
• 10242-11-2 5-bromobenzo[b]furan-2-carboxylic acid 

Relevant articles and documents

NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells

An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.

Multicomponent synthesis of substituted and fused-ring imidazoles via phospha-münchnone cycloaddition

A new, one-pot synthesis of imidazoles from imines, acid chlorides, and N-nosyl imines or tethered nitriles is reported. The reaction is mediated by the phosphonite PPh(catechyl) and proceeds via regioselective cycloaddition with an in situ-generated phos

Efficient synthesis of a benzo[b]furan building block

Unexpected difficulty in the conversion of a bromobenzofuran to the corresponding formylbenzofuran led us to develop a new synthesis for 5-formylbenzo[b]furan-2-carbonitrile (1). Copyright