Perfluorohexane
[CAS# 355-42-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: Perfluorohexane
• Synonyms: Tetradecafluorohexane; Tetradecafluoro-n-hexane
• Molecular Formula: C₆F₁₄
• Molecular Weight: 338.04
• CAS Registry Number: 355-42-0
• EC Number: 206-585-0
• SMILES: C(C(C(C(F)(F)F)(F)F)(F)F)(C(C(F)(F)F)(F)F)(F)F

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*, 1.669 g/mL (Expl.)
• Melting point: -74 °C (Expl.)
• Boiling point: 57.8±8.0 °C 760 mmHg (Calc.)^*, 58 - 60 °C (Expl.)
• Flash point: 1.2±10.2 °C (Calc.)^*
• Index of refraction: 1.248 (Calc.)^*, 1.252 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable liquids	Flam. Liq.	2	H225

Discovery and Applications

Perfluorohexane is a fully fluorinated derivative of hexane, where all hydrogen atoms are replaced with fluorine atoms. Its chemical formula is C₆F₁₄, and it belongs to the class of compounds known as perfluorocarbons (PFCs). These compounds are chemically and biologically inert, thermally stable, and have low surface tension and high gas solubility. Perfluorohexane is a clear, colorless, and odorless liquid under standard conditions and is notable for its unique physical and chemical properties.

The synthesis of perfluorohexane typically involves the electrochemical fluorination (ECF) of hexane or related hydrocarbon precursors using anhydrous hydrogen fluoride as the fluorine source. The process requires a nickel anode and yields a mixture of perfluorinated products, which are then separated and purified by distillation or other techniques. This method enables the replacement of hydrogen atoms with fluorine, producing highly stable C–F bonds that give perfluorohexane its remarkable properties.

Perfluorohexane has found application in several specialized fields due to its physicochemical characteristics. One of its most significant uses is in biomedical research and clinical applications as a blood substitute or oxygen carrier. Because of its high capacity to dissolve gases like oxygen and carbon dioxide, it has been investigated for use in liquid ventilation and organ preservation. Perfluorohexane can carry oxygen into hypoxic tissues when used in emulsified form, offering potential in therapeutic oxygen delivery and trauma care.

In imaging diagnostics, perfluorohexane is utilized as a contrast agent in ultrasound imaging when formulated into microbubble or nanodroplet emulsions. These emulsions respond to acoustic signals and can be targeted to specific tissues, enhancing the resolution and specificity of imaging. Additionally, its use has been explored in magnetic resonance imaging (MRI) and computed tomography (CT) as part of experimental contrast systems.

In materials science and electronics, perfluorohexane serves as a specialty solvent and coolant. Its high dielectric strength, chemical inertness, and low boiling point make it suitable for cleaning and cooling delicate components in semiconductor manufacturing and other precision electronic applications. Because it is non-flammable and chemically stable, it provides a safe medium for heat transfer in sensitive environments.

Environmental concerns have arisen regarding perfluorohexane and other PFCs due to their persistence in the environment and potential contribution to global warming. These compounds have long atmospheric lifetimes and high global warming potentials (GWP), prompting efforts to limit emissions and develop safer alternatives. Regulatory agencies monitor their production and use, especially in industrial applications.

Perfluorohexane is also employed in laboratory settings as a reference or inert diluent for studying chemical reactions under controlled conditions. Its chemical inertness allows it to be used as a medium that does not interfere with reaction pathways, making it valuable in mechanistic studies and material characterization.

Overall, perfluorohexane represents an important class of perfluorinated chemicals with broad utility in science and technology. Its applications in medicine, imaging, electronics, and research underscore the value of its unique properties, while also necessitating careful consideration of its environmental impact.

References

1973. Recent Advances in the Preparation and Use of Perfluorodecalin Emulsions for Tissue Perfusion. Advances in Experimental Medicine and Biology, 37.
DOI: 10.1007/978-1-4684-5089-7_7

2024. Investigation of Optimum Production Conditions and the Stability of β-Cyclodextrin-Perfluorocarbon Nanocone Clusters for Histotripsy Applications. Molecular Pharmaceutics, 21(4).
DOI: 10.1021/acs.molpharmaceut.3c01178

2024. Laser-activated perfluorocarbon nanodroplets for intracerebral delivery and imaging via blood-brain barrier opening and contrast-enhanced imaging. Journal of Nanobiotechnology, 22(1).
DOI: 10.1186/s12951-024-02601-6