16932-49-3

Basic information

• Product Name: 2,6-DIMETHOXYBENZONITRILE
• Synonyms: Benzonitrile, 2,6-dimethoxy-;2,6-DIMETHOXYBENZONITRILE;AKOS 227-44;2,6-Dimethoxybenzonitrile,97%;2,6-Dimethoxybenzenecarbonitrile;2,6-DIMETHOXYBENZONI;2,6 methoxybenzonitrile;2,6-dimethoxy-benzonitril
• CAS NO: 16932-49-3
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 241-000-2
• Product Categories: Aromatic Nitriles
• Mol File: 16932-49-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 119-123 °C
• Boiling Point: 310 °C
• Flash Point: 128.8°C
• Appearance: Light beige/Crystalline Powder
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 0.000758mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,6-DIMETHOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHOXYBENZONITRILE(16932-49-3)
• EPA Substance Registry System: 2,6-DIMETHOXYBENZONITRILE(16932-49-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 36/37-36-26
• Hazardous Substances Data: 16932-49-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 293, 1955Tetrahedron, 49, p. 10843, 1993 DOI: 10.1016/S0040-4020(01)80238-6

InChI:InChI=1/C9H9NO2/c1-11-8-4-3-5-9(12-2)7(8)6-10/h3-5H,1-2H3

Upstream product

• 38469-85-1 2-methoxy-6-nitrobenzonitrile 
• 16656-44-3 2.6-Dimethoxy-benzoyl-phosphonsaeurediethylester 
• 634-36-6 1,2,3-trimethoxybenzene 
• 151-50-8 potassium cyanide 
• 505-14-6 thiocyanogen 
• 151-10-0 1,3-Dimethoxybenzene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 630-18-2 tert-butyl isocyanide 
• 330660-35-0 silver cyanide 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 7321-55-3 2,2-dimethylmalononitrile 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 16932-44-8 2-iodo-1,3-dimethoxybenzene 

Downstream Products

• 61101-86-8 2,4,6-trihydroxy-2,6-dimethoxy-benzophenone 
• 20781-22-0 2,6-Dimethoxybenzylamine 
• 303-07-1 2,6-Dihydroxybenzoic acid 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 74-87-3 methylene chloride 
• 124-38-9 carbon dioxide 
• 108-46-3 recorcinol 
• 1000017-82-2 3,5-bis(2,6-dimethoxyphenyl)-1,2,4-oxadiazole 
• 791070-98-9 3-(2,6-dimethoxy-phenyl)-5-ethoxycarbonylmethyl-2-methyl-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester 

Relevant articles and documents

Zinc Oxide/Graphene Oxide as a Robust Active Catalyst for Direct Oxidative Synthesis of Nitriles from Alcohols in Water

In this work, without using any linker or chemical modification of graphene oxide, a zinc oxide immobilized graphene oxide-based catalyst was used for the direct aerobic oxidative conversion of alcohols to the nitriles in water. In the first step, graphene oxide was prepared and then zinc ions were electrostatically adsorbed onto the surface of graphene oxide. In the following step, zinc oxide nanoparticles were generated via in-situ growth in presence of NaOH. It was illustrated that graphene oxide layers can control the size of in-situ generated zinc oxide nanoparticles. Various aromatic/aliphatic/heteroaromatic primary alcohols converted to the nitriles in high yields under O2 balloon with ZnO/GO catalyst. This catalyst can be used for 7 successful consecutive runs without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]

Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution

Herein we describe a cation radical-accelerated-nucleophilic aromatic substitution (CRA-SNAr) of alkoxy arenes utilizing a highly oxidizing acridinium photoredox catalyst and acetone cyanohydrin, an inexpensive and commercially available cyanide source. This cyanation is selective for carbon-oxygen (C-O) bond functionalization and is applicable to a range of methoxyarenes and dimethoxyarenes. Furthermore, computational studies provide a model for predicting regioselectivity and chemoselectivity in competitive C-H and C-O cyanation of methoxyarene cation radicals.

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.