6609-56-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxybenzonitrile is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of drugs with diverse therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Methoxybenzonitrile is utilized as a starting material for the preparation of a wide range of organic compounds. Its reactivity and functional groups make it suitable for various chemical reactions, leading to the formation of new molecules with potential applications in different industries.
Used in the Synthesis of 5-(4′-methyl [1,1′-biphenyl]-2-yl)-1H-tetrazole:
Specifically, 2-Methoxybenzonitrile has been employed in the synthesis of 5-(4′-methyl [1,1′-biphenyl]-2-yl)-1H-tetrazole, a compound with potential applications in various fields. The use of 2-Methoxybenzonitrile in this synthesis highlights its importance as a versatile building block in the creation of complex organic molecules.

Preparation

o-Anisidine with sodium nitrite to make a diazonium salt solution, add it to the lead cyanide solution, and then add benzene. Put the mixture for 10-15h and carry out steam distillation, separate the benzene layer from the distillate, dry it with calcium chloride, evaporate the benzene, and distill the residue under reduced pressure, collect 120-122.5°C (1.2kPa fraction) to get 2-Methoxybenzonitrile, yield 64.5-67.3%.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 109, 1955 DOI: 10.1021/ja01606a035Synthesis, p. 641, 1992Tetrahedron Letters, 32, p. 1007, 1991 DOI: 10.1016/S0040-4039(00)74473-X

InChI:InChI=1/C8H7NO/c1-10-8-5-3-2-4-7(8)6-9/h2-5H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 99806-96-9 2-methoxy-benzaldehyde-((E)-O-benzoyl oxime ) 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 2439-77-2 2-methoxybenzamide 
• 90-04-0 2-methoxy-phenylamine 
• 611-20-1 salicylonitrile 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 612-24-8 o-nitrobenzonitrile 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 2944-48-1 2-tert-butylanisole 
• 143-33-9 sodium cyanide 

Downstream Products

• 5561-92-2 1-(2-methoxyphenyl)propan-1-one 
• 579-74-8 2-Methoxyacetophenone 
• 857550-38-0 2-methoxy-benzophenone-imine 
• 76405-55-5 N,N-dibutyl-2-methoxy-benzamidine 
• 6850-57-3 2-methoxybenzylamine 
• 51449-81-1 5-(2-methoxyphenyl)-1H-tetrazole 
• 578-58-5 2-methylmethoxybenzene 
• 17745-81-2 (1E,2E)-1,2-bis(2-methoxybenzylidene)hydrazine 
• 63452-53-9 N-acetyl-2-methoxybenzylamine 
• 135-02-4 ortho-anisaldehyde 
• 113016-89-0 5‐acetyl‐2‐methoxybenzonitrile 
• 33470-10-9 1-(2-methoxyphenyl)-2-phenylethanone 
• 5385-31-9 4-Indanyl-<2-methoxy-phenyl>-keton 
• 141510-92-1 6-cyano-6-<3'-(2-furyl)propyl>-1-methoxy-1,4-cyclohexadiene 

Relevant academic research and scientific papers

Photochemical Reactions in Polyethylene Glycol. 2. Photo-induced Nucleophilic Substitution of Dimethoxybenzenes in the Presence of Polyethylene Glycol

Polyethylene glycol can replace crown ether as co-solvent for photochemical substitution reactions of dimethoxybenzenes with KCN in CH2Cl2 in either the presence or the absence of terephthalonitrile.

Anomaluos Effects during Aromatic Nucleophilic Photosubstitutions of 2- and 4-Fluoroanisoles in Solvent Mixtures of Water and tert-Butyl Alcohol

The rate constant ratio for removal of fluorine by either cyano or hydroxy during aromatic nucleophilic photosubstitutions on 2- or 4-fluoroanisole displays a remarkable dependence upon the composition of the water/tert-butyl alcohol solvent and the distance between the methoxy group and the site of substitution in the solutes.

Nickel/zinc-mediated synthesis of aromatic nitriles from aromatic oxime ethers

Treatment of o-alkoxybenzaldoxime ethers 3 with an equimolar amount of NiCl2 and 3 equimolar amounts of Zn gave o-alkoxybenzonitriles 4 in good yields. It is suggested that the reaction proceed via coordination of the ether oxygen atom of alkyl

Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide

We examined the palladium-catalyzed cyanation of hindered, electron- rich aryl triflates by zinc cyanide using 2-methoxyphenyl trifluoromethanesulfonate (4 as a model compound. The reaction with two equivalents of Zn(CN)2 and catalytic Pd(PPh3)4 in DMF at 120°C for 2 hr afforded 2-methoxybenzonitrile (5) in 81% yield. The synthesis of 3-cyano-3- desoxynaltrexone (3), which had not previouly been obtained by the reaction with potassium or sodium cyanide as a cyanide source, was achieved by applying this procedure to its corresponding triflate 2.

Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst

A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.