Perfluoro-1-iodohexane
[CAS# 355-43-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: Perfluoro-1-iodohexane
• Synonyms: Tridecafluoro-1-iodohexane; Tridecafluorohexyl iodide; 1-Iodotridecafluorohexane; Perfluorohexyl iodide
• Molecular Formula: C₆F₁₃I
• Molecular Weight: 445.95
• CAS Registry Number: 355-43-1
• EC Number: 206-586-6
• SMILES: C(C(C(C(F)(F)I)(F)F)(F)F)(C(C(F)(F)F)(F)F)(F)F

Properties

• Density: 2.0±0.1 g/cm³ Calc.^*, 2.063 g/mL (Expl.)
• Melting point: -45 °C (Expl.)
• Boiling point: 117.1±8.0 °C 760 mmHg (Calc.)^*, 115 - 117 °C (Expl.)
• Flash point: 45.0±5.6 °C (Calc.)^*, 115 °C (Expl.)
• Solubility: water: insoluble (Expl.)
• Index of refraction: 1.333 (Calc.)^*, 1.329 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H411-H413
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H413
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Perfluoro-1-iodohexane (CAS 355-43-1) is a perfluorinated alkyl iodide with the molecular formula C₆F₁₃I and a molecular weight of 445.95 g mol⁻¹. It is also known as perfluorohexyl iodide, 1-iodoperfluorohexane, tridecafluorohexyl iodide, and n-perfluorohexyl iodide.

The compound is used as a fluorous chemical building block in perfluoroalkylation reactions and in materials chemistry, owing to its iodide functionality that enables radical or halogen-atom transfer chemistry in the presence of perfluoroalkyl radicals. It has been employed in visible-light-induced controlled radical polymerization of methacrylates, where perfluoro-1-iodohexane acts as the initiator in combination with a photoredox catalyst such as fac-[Ir(ppy)₃]. The C–I bond of the perfluoroalkyl iodide can homolyze under photochemical or thermal conditions, generating perfluoroalkyl radicals that initiate or control polymer growth.

Perfluoro-1-iodohexane is a light-pink liquid or oil at room temperature, with a density of approximately 2.063 g mL⁻¹ at 25 °C. Its melting point is around −45 °C, and its boiling point is about 117 °C under ambient conditions. It is insoluble in water and light-sensitive, requiring storage in tightly closed containers, protected from light and oxidizers.

This compound is widely used as a reactive intermediate in fluorous chemistry. It functions as a radical initiator and as a perfluoroalkyl source in organic synthesis or polymer modification. The iodide group serves as a labile transfer site for generating perfluoroalkyl radicals that can add to vinyl monomers, olefins, or other unsaturated substrates. In polymer chemistry, it allows the incorporation of perfluoroalkyl segments into polymers, enhancing their chemical resistance, thermal stability, and surface properties.

The perfluoroalkyl chain (–C₆F₁₃) provides exceptional stability and hydrophobicity, while the terminal iodide acts as a reactive functional handle. This makes perfluoro-1-iodohexane valuable in fluorous phase synthesis, surface functionalization, and the preparation of low-energy coatings.

In summary, perfluoro-1-iodohexane is a perfluoroalkyl iodide with the structural formula CF₃(CF₂)₅I, used as a key reagent in radical polymerization and surface modification chemistry. Its utility lies in the combination of a chemically inert perfluoroalkyl chain and a reactive iodine atom, enabling efficient radical-based transformations and material design.

References

Wang Y, Wang J, Li G-X, He G & Chen G (2017) Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions. Organic Letters 19(6) 1442–1445. DOI: 10.1021/acs.orglett.7b00375

Liu Q, Luo Q, Tong J, Shao Y, Shan W & Zhou H (2014) Visible light-induced controlled radical polymerization of methacrylates with perfluoroalkyl iodide as the initiator in conjugation with a photoredox catalyst fac-[Ir(ppy)₃]. Polymer 55(14) 3283–3291. DOI: 10.1002/pola.27390

Thermo Fisher Scientific (2024) Perfluoro-1-iodohexane (C₆F₁₃I), product specification / safety data sheet. Thermo Fisher Scientific. [https://www.thermofisher.com/order/catalog/product/269941000](https://www.thermofisher.com/order/catalog/product/269941000)