Production Method 1

89809-64-3

86869-14-9

Reaction Conditions

1.1 Reagents: Triethylamine ,  Water Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel ,  [2,2′-Bipyridine]-5,5′-diamine ,  Carbon nitride (C3N4) (graphitic) Solvents: Dimethylformamide ,  Acetonitrile ;  20 min; 12 h, 25 °C

Reference

Visible light-catalytic hydroxylation of aryl halides with water to phenols by carbon nitride and nickel complex cooperative catalysis

Wang, Kaixuan; et al, Green Chemistry, 2020, 22(21), 7417-7423

Production Method 2

41288-96-4

86869-14-9

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  0 °C; 4 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Dimethylformamide ;  16 h, 90 °C; 90 °C → rt
2.2 Reagents: Ammonia Solvents: Water
3.1 Reagents: Pyridinium chloride ;  6 h, 160 °C

Reference

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

Chekler, Eugene L. Piatnitski; et al, Journal of Medicinal Chemistry, 2014, 57(6), 2462-2471

Production Method 3

89809-64-3

86869-14-9

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: [2,2′-Bipyridine]-5,5′-dicarboxaldehyde, polymer with 4,4′,4′′-(1,3,5-triazine-2… (nickel complex) Solvents: Dimethylformamide ,  Acetonitrile ,  Water ;  20 min, rt; 24 h, 40 °C

Reference

Accelerated Direct Hydroxylation of Aryl Chlorides with Water to Phenols via the Proximity Effect in a Heterogeneous Metallaphotocatalyst

Wang, Kaixuan; et al, ACS Catalysis, 2022, 12(10), 6068-6080

Production Method 4

89809-63-2

86869-14-9

Reaction Conditions

1.1 Reagents: Pyridinium chloride ;  6 h, 160 °C

Reference

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

Chekler, Eugene L. Piatnitski; et al, Journal of Medicinal Chemistry, 2014, 57(6), 2462-2471

Production Method 5

86869-14-9

86869-14-9

Reaction Conditions

1.1 Reagents: Guanidine Solvents: Acetonitrile ;  70 °C

Reference

Parallel synthesis enablement of 2-pyridyl-5-cyano-pyrimidine-6-ones-a novel class of HIF-hydroxylase inhibitors

Chang, Shang-Poa; et al, Tetrahedron Letters, 2010, 51(6), 952-954

Production Method 6

139585-48-1

86869-14-9

Reaction Conditions

1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Dimethylformamide ;  16 h, 90 °C; 90 °C → rt
1.2 Reagents: Ammonia Solvents: Water
2.1 Reagents: Pyridinium chloride ;  6 h, 160 °C

Reference

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

Chekler, Eugene L. Piatnitski; et al, Journal of Medicinal Chemistry, 2014, 57(6), 2462-2471

5-hydroxypyridine-2-carbonitrile Raw materials

• 5-hydroxypyridine-2-carbonitrile
• 5-chloropyridine-2-carbonitrile
• 5-Methoxypyridine-2-carbonitrile
• 6-chloropyridin-3-ol
• 2-Chloro-5-methoxypyridine

5-hydroxypyridine-2-carbonitrile Preparation Products

• 5-hydroxypyridine-2-carbonitrile (86869-14-9)

• 1. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 2. An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting?
  Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei Huang J. Mater. Chem. A, 2020,8, 12518-12525
• 3. An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions?
  Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng Cao J. Mater. Chem. A, 2014,2, 7662-7665
• 4. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789
• 5. An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders
  Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li Yu Lab Chip, 2012,12, 317-324

Comprehensive Overview of 5-hydroxypyridine-2-carbonitrile (CAS No. 86869-14-9): Properties, Applications, and Industry Insights

5-hydroxypyridine-2-carbonitrile (CAS No. 86869-14-9) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and agrochemical research. This nitrile-functionalized pyridine derivative is characterized by its unique molecular structure, combining a hydroxyl group at the 5-position and a cyano group at the 2-position of the pyridine ring. Such structural features make it a versatile intermediate for synthesizing complex molecules, particularly in drug discovery and material science applications.

In recent years, the demand for high-purity 5-hydroxypyridine-2-carbonitrile has surged due to its role in developing kinase inhibitors and antiviral agents. Researchers are actively exploring its potential in targeting protein-protein interactions, a hot topic in precision medicine. The compound's ability to act as a hydrogen bond donor/acceptor enhances its binding affinity to biological targets, making it valuable for structure-activity relationship (SAR) studies.

From a synthetic chemistry perspective, 86869-14-9 serves as a critical building block for multi-step organic synthesis. Its reactivity patterns align with current trends in green chemistry, as it can participate in atom-efficient transformations like click chemistry and metal-catalyzed cross-coupling reactions. These properties address the growing industry need for sustainable chemical processes, a frequently searched topic in academic and industrial forums.

The analytical characterization of 5-hydroxypyridine-2-carbonitrile typically involves advanced techniques such as HPLC-MS and NMR spectroscopy, which are essential for verifying its purity – a key concern for researchers searching for reliable chemical suppliers. Recent publications have highlighted its stability under various pH conditions, making it suitable for formulation development in pharmaceutical applications.

Market analysts note increasing patent filings involving pyridine-2-carbonitrile derivatives, particularly in cancer therapeutics and neurodegenerative disease research. This aligns with search trends showing heightened interest in small molecule drug candidates. The compound's logP value and solubility profile make it particularly interesting for blood-brain barrier penetration studies, another trending research area.

Quality control standards for CAS 86869-14-9 have evolved significantly, with regulatory bodies emphasizing genotoxic impurity control – a frequently searched compliance topic. Leading manufacturers now employ quality-by-design (QbD) approaches to ensure batch-to-batch consistency, addressing common purchaser concerns about material traceability and technical documentation.

In material science applications, the electron-withdrawing nature of the cyano group in 5-hydroxypyridine-2-carbonitrile makes it valuable for designing organic semiconductors and photovoltaic materials. These applications tie into popular searches about renewable energy technologies and flexible electronics. Researchers are particularly interested in its potential for creating metal-organic frameworks (MOFs) with tailored porosity.

The compound's safety profile has been extensively documented, with particular attention to industrial handling procedures – a common concern among laboratory personnel. Material safety data sheets (MSDS) for 86869-14-9 emphasize standard personal protective equipment (PPE) requirements, aligning with workplace safety searches.

Looking forward, the development of continuous flow synthesis methods for hydroxypyridine derivatives represents an important industry trend. This addresses the growing demand for process intensification in chemical manufacturing – a topic frequently discussed in chemical engineering circles. The compound's stability under flow conditions makes it particularly suitable for these advanced production techniques.

For researchers investigating structure-property relationships, computational chemistry studies of 5-hydroxypyridine-2-carbonitrile have provided valuable insights into its electronic configuration and molecular orbitals. These findings contribute to the broader field of computer-aided drug design (CADD), a rapidly growing area of interest evidenced by search engine query trends.

• 727736-73-4(2,6-Pyridinedicarbonitrile,3-hydroxy-)
• 36057-44-0(4-Methoxypicolinonitrile)
• 6759-78-0(8-Hydroxyquinoline-2-carbonitrile)
• 886980-62-7(2-Pyridinecarbonitrile, 5-(methoxymethoxy)-)
• 89809-63-2(5-Methoxypyridine-2-carbonitrile)
• 932-35-4(3-hydroxypyridine-2-carbonitrile)
• 1121-78-4(6-methylpyridin-3-ol)
• 727736-69-8(3-Hydroxy-6-methylpicolinonitrile)
• 15462-43-8(2-Quinolinecarbonitrile,3-hydroxy-)
• 24059-89-0(3-Methoxypyridine-2-carbonitrile)