149384-09-8

Basic information

• Product Name: (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE
• Synonyms: (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE;2-(2-FORMYL-4-METHOXYPHENOXY)ACETONITRILE
• CAS NO: 149384-09-8
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.18
• Mol File: 149384-09-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 68-69°
• Boiling Point: 380.9±27.0 °C(Predicted)
• Appearance: /
• Density: 1.202±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE(149384-09-8)
• EPA Substance Registry System: (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE(149384-09-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 149384-09-8(Hazardous Substances Data)

Usage

General Description

(2-Formyl-4-methoxy-phenoxy)-acetonitrile is a chemical compound with a molecular formula C10H9NO3. It consists of a formyl group, a methoxy group, and an acetonitrile group attached to a phenoxy ring. (2-FORMYL-4-METHOXY-PHENOXY)-ACETONITRILE may have various industrial applications, including use as a building block in the synthesis of other organic compounds. It is important to handle this chemical with caution, as it may pose potential health hazards if not handled properly. Additionally, it is crucial to follow proper safety protocols and use appropriate protective equipment when working with this compound.

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 

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.

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%).