2-Fluoroethanol
[CAS# 371-62-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 2-Fluoroethanol
• Synonyms: 2-Fluoro-1-ethanol; Ethylene fluorohydrin
• Molecular Formula: C₂H₅FO
• Molecular Weight: 64.06
• CAS Registry Number: 371-62-0
• EC Number: 206-740-2
• SMILES: C(CF)O

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 1.091 g/mL
• Melting Point: -27 °C
• Index of Refraction: 1.326, Calc.^*, 1.365
• Boiling Point: 103.5±0.0 °C (760 mmHg), Calc.^*, 102-104 °C
• Flash Point: 31.1±0.0 °C, Calc.^*, 31 °C

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

Safety Data

• Hazard Symbols: GHS02;GHS06 Danger
• Risk Statements: H226-H300-H310-H330
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P262-P264-P270-P271-P280-P284-P301+P316-P302+P352-P303+P361+P353-P304+P340-P316-P320-P321-P330-P361+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	2	H300
Flammable liquids	Flam. Liq.	3	H226

Discovery and Applications

2-Fluoroethanol is a fluorinated alcohol that has garnered significant attention in the fields of organic chemistry and pharmaceuticals. The discovery of 2-fluoroethanol dates back to the early 20th century, coinciding with the growing interest in fluorinated compounds and their unique chemical properties. Fluorinated alcohols, including 2-fluoroethanol, are derived from the substitution of hydrogen atoms with fluorine, which significantly alters their physical and chemical characteristics.

The synthesis of 2-fluoroethanol typically involves the fluorination of ethanol. Various methods have been developed for this purpose, including nucleophilic substitution reactions and the use of fluorinating agents such as hydrogen fluoride or fluorine gas. The introduction of the fluorine atom at the second carbon position of the ethanol molecule imparts distinct properties that enhance its utility in various applications.

2-Fluoroethanol has found a wide range of applications in the pharmaceutical industry. Its ability to act as a building block in organic synthesis has led to its incorporation into the development of various bioactive compounds, including antiviral and antibacterial agents. The presence of the fluorine atom enhances the biological activity of these compounds, making them more potent and effective in treating diseases.

In addition to its pharmaceutical applications, 2-fluoroethanol serves as a useful solvent in chemical reactions. Its polar nature and ability to dissolve a wide variety of organic and inorganic substances make it an ideal medium for various synthetic processes. Moreover, its low volatility and low toxicity compared to other fluorinated solvents make it a safer alternative in laboratory settings.

The compound also exhibits unique properties that make it valuable in the field of materials science. 2-Fluoroethanol is used as a precursor in the synthesis of fluorinated polymers and materials, which possess enhanced thermal and chemical stability. These materials are sought after for applications in electronics, coatings, and specialty adhesives.

Recent studies have also investigated the potential of 2-fluoroethanol in biochemistry and medicinal chemistry. Research indicates that fluorinated alcohols can influence the behavior of biological molecules, leading to enhanced interactions with enzymes and receptors. This property positions 2-fluoroethanol as a promising candidate for developing new therapeutic agents and understanding biological processes at a molecular level.

In summary, 2-fluoroethanol is a significant fluorinated compound with a rich history of discovery and diverse applications in pharmaceuticals, materials science, and biochemistry. Its unique properties and versatility continue to drive research and innovation in various scientific fields, making it an important subject of ongoing investigation.

References

2023. Radiation-Initiated Dehalogenation of Organofluorine Compounds in Aqueous Solutions. High Energy Chemistry, 57(3).
DOI: 10.1134/s0018143923030153

2016. Charge collection kinetics on ferroelectric polymer surface using charge gradient microscopy. Scientific Reports, 6(1).
DOI: 10.1038/srep25087

2013. 2-[18F]Fluoroethanol and 3-[18F]fluoropropanol: facile preparation, biodistribution in mice, and their application as nucleophiles in the synthesis of [18F]fluoroalkyl aryl ester and ether PET tracers. Nuclear Medicine and Biology, 40(6).
DOI: 10.1016/j.nucmedbio.2013.04.009