Production Method 1

1193-62-0

1189-71-5

937-19-9

Reaction Conditions

1.1 Solvents: Dimethylformamide ,  Acetonitrile ;  -40 °C; -40 °C → rt; 24 h, rt

Reference

Dissecting the Complex Recognition Interfaces of Potent Tetrazole- and Pyrrole-Based Anion Binders

Pinter, Thomas; Simhadri, Chakravarthi; Hof, Fraser, Journal of Organic Chemistry, 2013, 78(10), 4642-4648

Production Method 2

263382-26-9

937-19-9

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  -20 °C; 30 min, -20 °C; 2 h, rt
1.2 Solvents: Water ;  rt

Reference

Synthesis of rhazinilam through intramolecular arylcyanation of alkenes catalyzed cooperatively by nickel/aluminum

Yamada, Yuuya; Ebata, Shiro; Hiyama, Tamejiro; Nakao, Yoshiaki, Tetrahedron, 2015, 71(26-27), 4413-4417

Production Method 3

848499-68-3

937-19-9

Reaction Conditions

1.1 Reagents: Titanium chloride (TiCl3) Solvents: Methanol ,  Water ;  3 h, 70 °C

Reference

Preparation of pyrroles as antibacterial agents

, World Intellectual Property Organization, , ,

Production Method 4

1193-62-0

1189-71-5

937-19-9

Reaction Conditions

Reference

Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles

Loader, Charles E.; Anderson, Hugh J., Canadian Journal of Chemistry, 1981, 59(17), 2673-6

Production Method 5

937-19-9

Reaction Conditions

Reference

Photochemistry of heterocyclic compounds. II. Photolysis of 2,6-dicyanopyridine 1-oxide

Ishikawa, Masayuki; Kaneko, Chikara; Yokoe, Ichiro; Yamada, Sachiko, Tetrahedron, 1969, 25(2), 295-300

Methyl 5-cyano-1H-pyrrole-2-carboxylate Raw materials

• 5-cyano-1-hydroxy-1H-Pyrrole-2-carboxylic acid methyl ester
• Methyl 5-((hydroxyimino)methyl)-1H-pyrrole-2-carboxylate
• Methyl 1H-pyrrole-2-carboxylate
• Chlorosulfonyl isocyanate

Methyl 5-cyano-1H-pyrrole-2-carboxylate Preparation Products

• Methyl 5-cyano-1H-pyrrole-2-carboxylate (937-19-9)

• 1. Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions?
  Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue Wu J. Mater. Chem. C, 2020,8, 17410-17416
• 2. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
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• 3. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 4. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 5. Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties?
  S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. Lee RSC Adv., 2014,4, 23107-23115

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids and derivatives

Methyl 5-cyano-1H-pyrrole-2-carboxylate (CAS No. 937-19-9): A Versatile Intermediate in Modern Chemical Biology

Methyl 5-cyano-1H-pyrrole-2-carboxylate (CAS No. 937-19-9) is a significant intermediate in the field of chemical biology, renowned for its structural versatility and functional adaptability. This compound, featuring a cyano-substituted pyrrole core, has garnered considerable attention in recent years due to its pivotal role in the synthesis of bioactive molecules and its potential applications in pharmaceutical research.

The Methyl 5-cyano-1H-pyrrole-2-carboxylate molecule is characterized by a pyrrole ring substituted at the 5-position with a cyano group and at the 2-position with a carboxylate ester. This unique structural motif makes it an invaluable building block for the construction of more complex heterocyclic systems. The cyano group introduces a polar electron-withdrawing nature, enhancing the reactivity of the molecule in various synthetic transformations, while the ester functionality provides a handle for further derivatization via hydrolysis or transesterification reactions.

In recent years, there has been a surge in research focused on developing novel therapeutic agents derived from pyrrole derivatives. The Methyl 5-cyano-1H-pyrrole-2-carboxylate has emerged as a key precursor in this endeavor, particularly in the synthesis of small-molecule inhibitors targeting various biological pathways. For instance, studies have demonstrated its utility in generating compounds with potential antimicrobial and anti-inflammatory properties. The cyano group, being a common pharmacophore, facilitates interactions with biological targets such as enzymes and receptors, thereby enhancing the pharmacological activity of the resulting molecules.

One of the most compelling aspects of Methyl 5-cyano-1H-pyrrole-2-carboxylate is its role in medicinal chemistry innovation. Researchers have leveraged this intermediate to develop novel scaffolds for drug discovery programs. The pyrrole core is a privileged structure in medicinal chemistry, known for its presence in numerous bioactive compounds across different therapeutic categories. By incorporating the cyano and ester functionalities, chemists can fine-tune the electronic and steric properties of their molecules, optimizing them for better bioavailability and target engagement.

The synthesis of Methyl 5-cyano-1H-pyrrole-2-carboxylate typically involves multi-step organic transformations starting from readily available pyrrole derivatives. Advanced synthetic methodologies, such as cross-coupling reactions and palladium-catalyzed processes, have been employed to achieve high yields and purity. These synthetic routes highlight the compound's importance as a synthetic intermediate and underscore the advancements in organic chemistry that facilitate its production.

In addition to its pharmaceutical applications, Methyl 5-cyano-1H-pyrrole-2-carboxylate has found utility in materials science and agrochemical research. Its ability to serve as a precursor for polymers and specialty chemicals underscores its broad applicability beyond traditional drug discovery contexts. The cyano group's incorporation into polymer backbones can enhance material properties such as thermal stability and mechanical strength, making this compound a valuable asset in industrial chemistry.

The growing interest in sustainable chemistry has also spurred research into greener synthetic routes for Methyl 5-cyano-1H-pyrrole-2-carboxylate. Recent studies have explored catalytic systems that minimize waste and energy consumption, aligning with global efforts to promote environmentally friendly chemical processes. These innovations not only improve the efficiency of producing this intermediate but also contribute to reducing the ecological footprint of chemical synthesis.

Future directions in the study of Methyl 5-cyano-1H-pyrrole-2-carboxylate are likely to focus on expanding its applications in drug discovery and materials science. The development of novel derivatives with enhanced biological activity or improved material properties will continue to drive interest in this versatile compound. As computational chemistry techniques advance, virtual screening methods will be increasingly employed to identify new applications for this intermediate, further solidifying its role as a cornerstone of modern chemical biology.

In conclusion, Methyl 5-cyano-1H-pyrrole-2-carboxylate (CAS No. 937-19-9) represents a critical building block with far-reaching implications across multiple scientific disciplines. Its unique structural features and reactivity make it indispensable in pharmaceutical research, materials science, and agrochemical development. As advancements continue to unfold in synthetic chemistry and drug discovery, the importance of this compound is expected to grow even further.

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