1211535-54-4 | 2-AMINO-5-FLUORO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER

CAS:1211535-54-4 | 2-AMINO-5-FLUORO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER,Description

Methyl 2-amino-5-fluoronicotinate is a chemical compound with the molecular formula C7H7FN2O2. It has a molecular weight of 170.14. The IUPAC name for this compound is methyl 2-amino-5-fluoronicotinate. It is typically stored in a dark place, under an inert atmosphere, at temperatures between 2-8°C.

Synthesis Analysis

The synthesis of Methyl 2-amino-5-fluoronicotinate involves several steps. In one method, isopropylamine is combined with sulfonic chloride acid and triethylamine in 1,2-dichloro-ethane at 0 - 10℃ for 0.166667h. Then, methyl 2-amino-5-fluoropyridine-3-carboxylate is added and the mixture is heated at 35℃ for 0.5h. Finally, the mixture is treated with trichlorophosphate in 1,2-dichloro-ethane at 35 - 55℃.

Molecular Structure Analysis

The InChI code for Methyl 2-amino-5-fluoronicotinate is 1S/C7H7FN2O2/c1-12-7(11)5-2-4(8)3-10-6(5)9/h2-3H,1H3,(H2,9,10). The compound has a total of 12 heavy atoms.

Physical And Chemical Properties Analysis

Methyl 2-amino-5-fluoronicotinate is a solid at room temperature. It has a topological polar surface area of 65.2 Ų. The compound has a hydrogen bond donor count of 1 and a hydrogen bond acceptor count of 5. It has a rotatable bond count of 2.

Scientific Research Applications

Synthesis and Chemical Properties

• Methyl 2-amino-5-fluoronicotinate is utilized in the practical synthesis of pharmaceutical intermediates. One such synthesis involves palladium-catalyzed cyanation and reduction sequences, highlighting its role in complex chemical procedures (Wang et al., 2006).

Applications in Organic and Medicinal Chemistry

• It finds applications in the preparation of compounds like 2'-deoxyoligonucleotides containing 5-fluorocytidine, which are significant in studying DNA methylation processes (Schmidt et al., 1992).
• Its derivatives have been explored in the development of selective, potent, and orally active agonists at 5-HT1A receptors, demonstrating its potential in the design of new drugs for mental health disorders (Vacher et al., 1999).

Analytical Chemistry and Detection Techniques

• It is involved in the development of methods for the separation and determination of compounds like 5-fluoronicotinic acid and ethyl 5-fluoronicotinate, indicating its role in refining analytical chemistry techniques (Hu Bao-xiang, 2005).

Fluorescent and Optical Applications

• Methyl 2-amino-5-fluoronicotinate and related compounds have applications in the design and synthesis of fluorescent amino acids. These are crucial for non-invasive studies in cells and organisms, enhancing our understanding of molecular biology (Cheng et al., 2020).

Synthesis Optimization

• There has been research focused on optimizing the synthesis method for Methyl 2-amino-5-fluorobenzoate, a related compound, indicating the ongoing efforts to improve the efficiency and yield of synthesizing such chemicals (Yin Jian-zhong, 2010).

Biochemical Pharmacology

• The compound has been indirectly involved in studies related to ornithine decarboxylase inhibition, which is crucial for understanding certain biochemical pathways and their implications in diseases (Mamont et al., 1986).

Safety And Hazards

Methyl 2-amino-5-fluoronicotinate is associated with several hazard statements including H302, H315, H319, and H335. The compound should be handled with care to avoid ingestion and inhalation. It is recommended to use personal protective equipment and avoid dust formation.

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