108656-11-7

Usage

Nitrile derivative

2-formyl-5-methoxyphenol The compound is derived from 2-formyl-5-methoxyphenol by introducing an acetonitrile functional group.

Benzene ring

Formyl and methoxy group attached The benzene ring structure has a formyl group (-CHO) and a methoxy group (-OCH3) attached to it, which influence its chemical properties and reactivity.

Acetonitrile functional group

Versatile building block The presence of the acetonitrile group (-C≡N) suggests that 2-(2-formyl-5-methoxyphenoxy)acetonitrile can be used as an intermediate in the synthesis of other organic compounds, as acetonitriles are known for their versatility in organic chemistry.

Specific properties and potential uses

Dependent on further research The exact properties and applications of 2-(2-formyl-5-methoxyphenoxy)acetonitrile would need to be determined through additional experimental studies and research.

Upstream product

• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 590-17-0 cyanomethyl bromide 
• 50635-23-9 (3-methoxyphenoxy)acetonitrile 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 64915-37-3 3-amino-7-methoxy-4H-chromen-4-one 
• 1361959-79-6 (6-hydroxybenzofuran-2-yl)(p-tolyl)methanone 
• 309290-76-4 (6-methoxybenzofuran-2-yl)(p-tolyl)methanone 
• 683764-13-8 (4-fluorophenyl)(6-methoxy-1-benzofuran-2-yl)methanone 
• 683764-14-9 (6-methoxybenzofuran-2-yl)(4-fluorophenyl)methanol 
• 53020-44-3 6-hydroxybenzofuran-2-carbonitrile 

Relevant academic research and scientific papers

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.

Novel heterocyclic analogues of firefly luciferin

Five novel firefly luciferin analogues in which the benzothiazole ring system of the natural substrate was replaced with benzimidazole, benzofuran, benzothiophene, benzoxazole, and indole were synthesized. The fluorescence, bioluminescence, and kinetic pr

N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones

(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).

Amine compounds, their production and use

The present invention provides a compound of the formula: wherein Ar represents an aromatic group which may be substituted; X represents methylene, S, SO, SO2or CO; Y represents a spacer having a main chain of 2 to 5 atoms; n represents an integer of 1 to 5; i) R1and R2each represents a hydrogen atom or a lower alkyl which may be substituted, ii) R1and R2form, taken together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted, or iii) R1or R2together with —(CH2)n—N═ form, bonded to a component atom of Ring B, a spiro-ring which may be substituted; Ring A represents an aromatic ring which may be substituted; Ring B represents a 4- to 7-membered nitrogen-containing non-aromatic ring which may be further substituted by alkyl or acyl, with a proviso that X represents S, SO, SO2or CO when Ring A has as a substituent a group represented by the formula: —NHCOR11 where R11represents alkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or a group represented by the formula: —NHR12 where R12represents alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or a salt thereof; which has an excellent somatostatin receptor binding inhibition action.

A Novel Synthesis of Benzofuran and Related Compounds. I. The Vilsmeier Reaction of Phenoxyacetonitriles

A novel synthesis of 2-benzofurancarboxylic acid derivatives by the Vilsmeier reaction of phenoxyacetonitriles is described.