Production Method 1

1350932-95-4

89809-63-2

Reaction Conditions

1.1 Reagents: Sodium nitrite Solvents: Dimethylformamide ;  5 h, 100 °C

Reference

Dual Utility of Heterogeneous Catalyst ZSM-5 for C-C Cleavage Leading to Nitriles, and for the Synthesis of Hydrazides

Ghodse, Shrikant M.; Takale, Balaram S.; Hatvate, Navnath T.; Telvekar, Vikas N., ChemistrySelect, 2018, 3(16), 4168-4172

Production Method 2

97483-77-7

89809-63-2

Reaction Conditions

1.1 Reagents: Quinuclidine Catalysts: Dichloro[1,2-di(methoxy-κO)ethane]nickel ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Acetonitrile ;  40 h, rt

Reference

Solar-driven tandem photoredox nickel-catalysed cross-coupling using modified carbon nitride

Qin, Yangzhong; Martindale, Benjamin C. M.; Sun, Rui; Rieth, Adam J.; Nocera, Daniel G., Chemical Science, 2020, 11(28), 7456-7461

Production Method 3

139585-48-1

89809-63-2

Reaction Conditions

1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Dimethylformamide ;  16 h, 90 °C; 90 °C → rt
1.2 Reagents: Ammonia Solvents: Water

Reference

1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

Chekler, Eugene L. Piatnitski; Unwalla, Rayomond; Khan, Taukeer A.; Tangirala, Raghuram S.; Johnson, Mark; et al, Journal of Medicinal Chemistry, 2014, 57(6), 2462-2471

Production Method 4

55270-47-8

89809-63-2

Reaction Conditions

1.1 Reagents: Acetyl chloride ,  Sodium nitrite Solvents: 1,4-Dioxane ;  11 h, 140 °C; 140 °C → rt
1.2 Reagents: tert-Butyl hydroperoxide ,  Sodium carbonate Solvents: Water ;  rt

Reference

Direct Transformation of Nitrogen-Containing Methylheteroarenes to Heteroaryl Nitrile by Sodium Nitrite

Jiang, Chenhui; Chen, Yuqin; Gao, Pan ; Zhang, Shuwei; Jia, Xiaodong ; et al, Organic Letters, 2022, 24(34), 6341-6345

Production Method 5

97483-77-7

89809-63-2

Reaction Conditions

1.1 Reagents: Quinuclidine Catalysts: 2,2′-Bipyridine ,  Nickel dichloride ,  [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, polymer with 5′-(4-aminophenyl)[… Solvents: Dimethylacetamide ;  10 h

Reference

Covalent organic frameworks editing for efficient metallaphotoredox catalytic carbon-oxygen cross coupling of aryl halides with alcohols

Meng, Di; Xue, Jing; Zhang, Yufan; Liu, Tianjiao; Chen, Chuncheng; et al, Catalysis Science & Technology, 2023, 13(5), 1518-1526

Production Method 6

327056-62-2

89809-63-2

Reaction Conditions

1.1 Solvents: Methanol ;  12 h, reflux

Reference

Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)-H Bonds

He, Gang; Zhang, Shu-Yu; Nack, William A.; Li, Qiong; Chen, Gong, Angewandte Chemie, 2013, 52(42), 11124-11128

5-Methoxypyridine-2-carbonitrile Raw materials

• 5-Methoxy-2-methylpyridine
• 1-(5-methoxypyridin-2-yl)propan-2-one
• 5-Bromopicolinonitrile
• 5-Fluoro-2-pyridinecarbonitrile
• 2-Chloro-5-methoxypyridine

5-Methoxypyridine-2-carbonitrile Preparation Products

• 5-Methoxypyridine-2-carbonitrile (89809-63-2)

• 1. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 2. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 3. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 4. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 5. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Alkyl aryl ethers
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ethers Alkyl aryl ethers

Introduction to 5-Methoxypyridine-2-carbonitrile (CAS No. 89809-63-2)

5-Methoxypyridine-2-carbonitrile, with the chemical formula C?H?NO?, is a significant compound in the field of pharmaceutical and chemical research. This heterocyclic organic molecule features a pyridine core substituted with a methoxy group at the 5-position and a nitrile group at the 2-position. Its unique structural properties make it a valuable intermediate in the synthesis of various biologically active molecules, particularly in the development of novel therapeutic agents.

The compound is identified by its CAS number, CAS No. 89809-63-2, which serves as a unique identifier in scientific literature and databases. This numbering system ensures precise classification and retrieval of information related to its properties, synthesis, and applications. The presence of both electron-withdrawing and electron-donating groups in its structure contributes to its reactivity and makes it a versatile building block in organic synthesis.

Recent advancements in medicinal chemistry have highlighted the importance of 5-Methoxypyridine-2-carbonitrile in the design of small-molecule drugs. Its pyridine ring is a common motif in many pharmacologically active compounds due to its ability to interact with biological targets such as enzymes and receptors. The methoxy group enhances solubility and metabolic stability, while the nitrile group provides a site for further functionalization, enabling the creation of more complex derivatives.

In particular, researchers have been exploring the potential of 5-Methoxypyridine-2-carbonitrile in the development of treatments for neurological disorders. Studies have demonstrated that pyridine derivatives can modulate neurotransmitter systems, making them promising candidates for drugs targeting conditions such as Alzheimer's disease and Parkinson's disease. The methoxy and nitrile substituents play crucial roles in fine-tuning the pharmacokinetic and pharmacodynamic properties of these derivatives.

The synthesis of 5-Methoxypyridine-2-carbonitrile typically involves multi-step reactions starting from readily available precursors. One common synthetic route includes the nucleophilic substitution of a halogenated pyridine derivative with methanol, followed by cyanation using a suitable cyanating agent. These reactions are often catalyzed by transition metals or acid/base conditions to enhance efficiency and yield.

Recent research has also focused on green chemistry approaches to improve the sustainability of synthesizing 5-Methoxypyridine-2-carbonitrile. Innovations such as solvent-free reactions, catalytic methods using biodegradable materials, and microwave-assisted synthesis have been explored to minimize waste and energy consumption. These methods align with global efforts to promote environmentally friendly chemical processes.

The applications of 5-Methoxypyridine-2-carbonitrile extend beyond pharmaceuticals into agrochemicals and materials science. In agrochemistry, pyridine derivatives are used as intermediates in the production of pesticides and herbicides due to their efficacy in protecting crops from pests and diseases. Additionally, their electronic properties make them useful in designing advanced materials such as organic semiconductors and catalysts.

In conclusion, 5-Methoxypyridine-2-carbonitrile (CAS No. 89809-63-2) is a multifaceted compound with significant potential in various scientific domains. Its unique structure and reactivity make it an indispensable tool for researchers developing new drugs, agrochemicals, and advanced materials. As our understanding of its properties continues to grow, so too will its applications in addressing global challenges in health, agriculture, and technology.

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• 886980-62-7(2-Pyridinecarbonitrile, 5-(methoxymethoxy)-)
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