Production Method 1

40473-07-2

83621-01-6

Reaction Conditions

1.1 Catalysts: Triphenylphosphine (polymer bound) ,  Palladium diacetate Solvents: Dimethylformamide ;  2 h
1.2 30 min, 140 °C; 140 °C → rt

Reference

Application of polymer-supported triphenyl phosphine in the palladium-catalyzed cyanation reaction under microwave conditions

Srivastava, Rajiv R.; et al, Tetrahedron Letters, 2004, 45(48), 8895-8897

Production Method 2

54221-96-4

83621-01-6

Reaction Conditions

1.1 Reagents: Ammonium acetate ,  Iodobenzene diacetate Solvents: 1,2-Dichloroethane ;  1 h, rt → 40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Metal-Free, Oxidative Condensation of Heteroaryl- and Aryl Carbaldehydes towards Functionalized Carbonitriles

Agyei, Eric A.; et al, ChemistrySelect, 2023, 8(23),

Production Method 3

40473-07-2

83621-01-6

Reaction Conditions

1.1 Solvents: Dimethylformamide
1.2 Reagents: Hydrochloric acid ,  Iron chloride (FeCl3) Solvents: Water

Reference

Cascade radical synthesis of heteroarenes via iminyl radicals

Bowman, W. Russell; et al, Journal of the Chemical Society, 2002, (1), 58-68

Production Method 4

20773-98-2

83621-01-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Trimethylsilyl cyanide Solvents: Acetonitrile

Reference

Site-selectivity in the cyanation of 3-substituted pyridine 1-oxides with trimethylsilanecarbonitrile

Sakamoto, Takao; et al, Chemical & Pharmaceutical Bulletin, 1985, 33(2), 565-71

Production Method 5

626-05-1

83621-01-6

Reaction Conditions

1.1 Solvents: Methanol
2.1 Solvents: Dimethylformamide
2.2 Reagents: Hydrochloric acid ,  Iron chloride (FeCl3) Solvents: Water

Reference

Cascade radical synthesis of heteroarenes via iminyl radicals

Bowman, W. Russell; et al, Journal of the Chemical Society, 2002, (1), 58-68

Production Method 6

40473-07-2

83621-01-6

Reaction Conditions

1.1 Catalysts: [2′-(Amino-κN)[1,1′-biphenyl]-2-yl-κC][bis(1,1-dimethylethyl)[2′,4′,6′-tris(1-me… Solvents: Tetrahydrofuran ,  Water ;  18 h, 40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  5 min, rt

Reference

Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media

Cohen, Daniel T.; et al, Organic Letters, 2015, 17(2), 202-205

Production Method 7

17228-64-7

83621-01-6

Reaction Conditions

1.1 Catalysts: Dipiperidinomethane ,  Palladium diacetate ,  1,5-Bis(diphenylphosphino)pentane Solvents: Toluene ;  16 h, 160 °C

Reference

Progress in the palladium-catalyzed cyanation of aryl chlorides

Sundermeier, Mark; et al, Chemistry - A European Journal, 2003, 9(8), 1828-1836

Production Method 8

1158818-46-2

83621-01-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  4-Nitro-1-[(trifluoromethyl)sulfonyl]-1H-imidazole Solvents: Acetonitrile ;  10 min, rt

Reference

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

Zhang, Wei; et al, Chemical Communications (Cambridge, 2020, 56(46), 6221-6224

Production Method 9

100-70-9

83621-01-6

Reaction Conditions

Reference

Substitution of cyano group by hydroxyalkyl group and of ring hydrogen by alkoxy group in UV irradiation of 2-pyridinecarbonitrile in alcohols

Sugimori, Akira; et al, Bulletin of the Chemical Society of Japan, 1982, 55(9), 2906-10

6-Methoxypyridine-2-carbonitrile Raw materials

• 2,6-Dibromopyridine
• pyridine, 2-methoxy-, 1-oxide
• 2-Bromo-6-methoxypyridine
• 2-Pyridinecarboxaldehyde, 6-methoxy-, oxime
• pyridine-2-carbonitrile
• 6-methoxypyridine-2-carbaldehyde
• 2-Chloro-6-methoxypyridine

6-Methoxypyridine-2-carbonitrile Preparation Products

• 6-Methoxypyridine-2-carbonitrile (83621-01-6)

• 1. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 2. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 3. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 4. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 5. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378

• Solvents and Organic Chemicals Organic Compounds cyanides/Cyanides

Introduction to 6-Methoxypyridine-2-carbonitrile (CAS No. 83621-01-6)

6-Methoxypyridine-2-carbonitrile, identified by the Chemical Abstracts Service Number (CAS No.) 83621-01-6, is a significant intermediate in the realm of organic synthesis and pharmaceutical chemistry. This compound, featuring a pyridine core substituted with a methoxy group at the 6-position and a nitrile group at the 2-position, has garnered attention due to its versatile reactivity and utility in constructing complex molecular architectures.

The structural motif of 6-methoxypyridine-2-carbonitrile makes it a valuable building block for the synthesis of various pharmacologically relevant molecules. The presence of both electron-withdrawing and electron-donating groups enhances its participation in diverse chemical transformations, including nucleophilic substitution, condensation reactions, and metal-catalyzed cross-coupling processes. These characteristics have positioned it as a key precursor in the development of novel therapeutic agents.

In recent years, 6-methoxypyridine-2-carbonitrile has been extensively explored in the context of drug discovery and medicinal chemistry. Its incorporation into heterocyclic scaffolds has led to the identification of compounds with promising biological activities. For instance, derivatives of this scaffold have been investigated for their potential antimicrobial, anti-inflammatory, and anticancer properties. The methoxy group at the 6-position provides a handle for further functionalization, allowing chemists to tailor the electronic and steric properties of the molecule to optimize biological efficacy.

One notable application of 6-methoxypyridine-2-carbonitrile is in the synthesis of kinase inhibitors, which are critical in targeted cancer therapies. The pyridine ring serves as a privileged structure in many kinase inhibitors due to its ability to form hydrogen bonds with key residues in the active site of the enzyme. The nitrile group at the 2-position can be further modified to introduce additional binding interactions or to modulate solubility and metabolic stability. Recent studies have demonstrated that 6-methoxypyridine-2-carbonitrile derivatives exhibit inhibitory activity against various kinases, making them attractive candidates for further development.

The pharmaceutical industry has also leveraged 6-methoxypyridine-2-carbonitrile in the design of central nervous system (CNS) drugs. The pyridine scaffold is commonly found in psychoactive substances due to its ability to cross the blood-brain barrier efficiently. Researchers have utilized 6-methoxypyridine-2-carbonitrile as a core structure to develop novel compounds with potential applications in treating neurological disorders such as depression, anxiety, and epilepsy. The methoxy group facilitates further derivatization, enabling fine-tuning of pharmacokinetic and pharmacodynamic profiles.

Moreover, 6-methoxypyridine-2-carbonitrile has found utility beyond pharmaceuticals in agrochemical research. Its structural features make it a suitable candidate for synthesizing bioactive molecules that can interact with biological targets involved in plant growth regulation and pest control. The compound’s ability to undergo diverse chemical transformations allows for the creation of novel agrochemicals with enhanced efficacy and environmental compatibility.

The synthetic methodologies employed in preparing 6-methoxypyridine-2-carbonitrile are also worth mentioning. One common approach involves the nitrilation of 6-methoxypyridine using cyanating agents such as cyanogen bromide or copper(I) cyanide under controlled conditions. Alternatively, palladium-catalyzed cross-coupling reactions can be utilized to introduce the nitrile group selectively at the 2-position. These synthetic strategies highlight the compound’s adaptability and ease of functionalization, contributing to its widespread use in industrial applications.

In conclusion, 6-methoxypyridine-2-carbonitrile (CAS No. 83621-01-6) is a multifaceted compound with significant applications across multiple domains of chemistry and biology. Its structural versatility and reactivity make it an indispensable intermediate in drug discovery, agrochemical synthesis, and material science. As research continues to uncover new applications for this compound, its importance is likely to grow further, solidifying its role as a cornerstone in modern chemical synthesis.

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