1,6-Diiodododecafluorohexane
[CAS# 375-80-4]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1,6-Diiodododecafluorohexane
• Synonyms: 1,6-Diiodoperfluorohexane
• Molecular Formula: C₆F₁₂I₂
• Molecular Weight: 553.85
• CAS Registry Number: 375-80-4
• EC Number: 206-794-7
• SMILES: C(C(C(C(F)(F)I)(F)F)(F)F)(C(C(F)(F)I)(F)F)(F)F

Properties

• Density: 2.357 g/mL
• Melting point: 25 ºC
• Boiling point: 115 ºC (100 mmHg)
• Flash point: 25 ºC
• Refractive index: 1.398

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P271-P280

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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

1,6-Diiodododecafluorohexane is a highly fluorinated organic compound featuring both iodine and fluorine atoms in its structure. Its synthesis and applications highlight its importance in various chemical and industrial fields.

The discovery of 1,6-diiodododecafluorohexane dates back to research on fluorinated and iodinated compounds, which gained prominence in the latter half of the 20th century. The compound is notable for its highly fluorinated hexane backbone, where iodine atoms are positioned at the 1 and 6 positions of the dodecafluorohexane chain. The remaining carbon atoms are substituted with fluorine atoms, resulting in a molecule with a total of twelve fluorine atoms and two iodine atoms.

The synthesis of 1,6-diiodododecafluorohexane typically involves a multi-step process starting from a fluorinated hexane precursor. The synthesis includes selective iodination of the hexane backbone, followed by further fluorination to achieve the desired level of fluorine substitution. The process requires precise control of reaction conditions to ensure the successful incorporation of iodine and fluorine atoms into the hexane chain.

One of the key applications of 1,6-diiodododecafluorohexane is in the field of organic synthesis. The compound serves as a valuable reagent for introducing both iodine and fluorine functionalities into other organic molecules. Its high degree of fluorination and iodination makes it particularly useful for preparing specialized compounds in pharmaceuticals and agrochemicals, where such functionalities can impart unique properties.

In materials science, 1,6-diiodododecafluorohexane is used to modify the properties of polymers and materials. The presence of iodine and fluorine enhances the chemical stability, thermal resistance, and mechanical properties of materials. This makes the compound useful for producing high-performance materials that can withstand harsh environmental conditions and have improved durability.

Furthermore, 1,6-diiodododecafluorohexane finds applications in the field of environmental science. Its stability and reactivity profiles make it useful for studying the behavior and impact of halogenated compounds in various environmental contexts. Researchers use it to investigate the persistence and degradation pathways of similar fluorinated and iodinated substances, contributing to a better understanding of their environmental impact.

Handling 1,6-diiodododecafluorohexane requires caution due to the reactive nature of its halogenated components. Proper safety measures, including the use of personal protective equipment and working in well-ventilated areas, are essential to minimize exposure to potentially harmful fumes and ensure safe handling.

Overall, 1,6-diiodododecafluorohexane is a significant compound in organofluorine chemistry with diverse applications in synthesis, materials science, and environmental research. Its unique combination of iodine and fluorine atoms imparts distinctive properties that are valuable for various industrial and scientific purposes.

References

2023. Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP. Chinese Journal of Polymer Science, 41(10).
DOI: 10.1007/s10118-023-3003-6

2017. Weakening and Leveling Effect of Solvent Polarity on Halogen Bond Strength of Diiodoperfluoroalkane with Halide. Journal of Solution Chemistry, 46(5).
DOI: 10.1007/s10953-017-0623-x

2015. Synthesis and thermal behavior of triblock semifluorinated n-alkanes. Journal of Thermal Analysis and Calorimetry, 123(3).
DOI: 10.1007/s10973-015-5149-0