5-Fluoro-2-pyrimidinemethanol
[CAS# 1227574-72-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Fluoropyrimidine
• Name: 5-Fluoro-2-pyrimidinemethanol
• Molecular Formula: C₅H₅FN₂O
• Molecular Weight: 128.10
• CAS Registry Number: 1227574-72-2
• SMILES: C1=C(C=NC(=N1)CO)F

Properties

• Solubility: Freely soluble (143 g/L) (25 ºC), Calc.^*
• Density: 1.364±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.527, Calc.^*
• Boiling point: 200.3±20.0 ºC (760 Torr), Calc.^*
• Flash point: 74.9±21.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

5-Fluoro-2-pyrimidinemethanol is an organofluorine compound with growing significance in medicinal chemistry. Structurally, it consists of a pyrimidine ring, a methanol group at the second carbon position, and a fluorine atom attached to the fifth carbon. This compound’s unique structure has made it a key building block in synthesizing various biologically active molecules, particularly in the pharmaceutical industry. Compounds containing a fluorine atom within heterocyclic structures, such as pyrimidines, often exhibit enhanced bioavailability and metabolic stability, making them attractive for drug development.

The discovery of 5-fluoro-2-pyrimidinemethanol stems from the broader effort to develop fluorinated compounds for therapeutic applications. Fluorination has long been recognized as an effective strategy to modify the chemical and physical properties of drug candidates. The introduction of a fluorine atom, as in this compound, can enhance a molecule’s lipophilicity, improve its binding affinity to biological targets, and increase its resistance to metabolic degradation. This has led to the widespread use of fluorinated pyrimidines in developing antiviral and anticancer agents.

Applications of 5-fluoro-2-pyrimidinemethanol are primarily focused on its role as an intermediate in synthesizing drugs and other biologically active compounds. The presence of the fluorine atom allows the compound to participate in selective reactions, aiding in the synthesis of derivatives with targeted biological activities. In oncology research, compounds derived from 5-fluoro-2-pyrimidinemethanol have been evaluated for their ability to inhibit nucleic acid synthesis, a property critical in controlling cancer cell proliferation. The fluorinated pyrimidine ring can disrupt the synthesis of thymidine, a nucleoside essential for DNA replication, thereby inducing cell cycle arrest and promoting apoptosis in rapidly dividing cancer cells.

Another notable application of 5-fluoro-2-pyrimidinemethanol is in antiviral research, where pyrimidine derivatives have shown efficacy in inhibiting viral replication. The methanol group at the second position enables this compound to interact effectively with viral enzymes, interfering with their replication mechanisms. This activity has been particularly valuable in designing therapies against DNA viruses, which rely on nucleoside analogs for effective treatment. The modification of 5-fluoro-2-pyrimidinemethanol with additional functional groups further enhances its antiviral properties, offering a flexible scaffold for developing new antiviral agents.

Additionally, 5-fluoro-2-pyrimidinemethanol is used in agricultural chemistry to develop plant protection agents. Its derivatives are explored for their potential to inhibit fungal and bacterial growth, contributing to crop protection and yield improvement. The compound’s structure allows for specific targeting of pathogenic enzymes, minimizing environmental impacts while maintaining effectiveness. This selective mechanism supports its application in environmentally friendly pest management practices.