1,1,2,2-Tetrafluoro-1,4-diiodobutane
[CAS# 755-95-3]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1,1,2,2-Tetrafluoro-1,4-diiodobutane
• Molecular Formula: C₄H₄F₄I₂
• Molecular Weight: 381.88
• CAS Registry Number: 755-95-3
• SMILES: C(CI)C(C(F)(F)I)(F)F

Properties

• Solubility: 0.06026 mg/L (25 ºC water)
• Density: 2.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.523, Calc.^*
• Melting point: -5.43 ºC
• Boiling Point: 201.75 ºC, 195.0±8.0 ºC (760 mmHg), Calc.^*
• Flash Point: 76.3±5.6 ºC, Calc.^*

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

Discovory and Applicatios

1,1,2,2-Tetrafluoro-1,4-diiodobutane is a halogenated organic compound known for its unique combination of iodine and fluorine atoms. The discovery of this compound is linked to the broader exploration of fluorinated and iodinated molecules, driven by their potential utility in various chemical and industrial applications. Fluorinated compounds are especially valued for their chemical stability, low reactivity, and thermal resistance, while iodinated compounds are often used for their reactivity and ability to form strong bonds in organic synthesis.

The structure of 1,1,2,2-tetrafluoro-1,4-diiodobutane, which includes both fluorine and iodine atoms, offers a balance of chemical stability and reactivity. This makes it a valuable intermediate in organic chemistry, where it can be used in various synthetic pathways. The fluorine atoms contribute to the compound’s resistance to chemical degradation, while the iodine atoms provide reactive sites for further functionalization, making it a versatile reagent in the development of more complex organic molecules.

In industrial applications, this compound can be used in the production of specialty chemicals and materials, particularly in the field of advanced polymer synthesis. Fluorinated polymers, known for their high-performance characteristics, benefit from the inclusion of compounds like 1,1,2,2-tetrafluoro-1,4-diiodobutane, which can introduce specific properties such as hydrophobicity, chemical resistance, and thermal stability. These materials find use in coatings, sealants, and insulation for extreme environments.

The compound's dual halogenation also makes it useful in medicinal chemistry, where fluorine and iodine atoms are frequently incorporated into drug candidates to enhance bioavailability, metabolic stability, and imaging properties. Iodinated compounds, in particular, are used in radiocontrast agents and other diagnostic tools due to their ability to absorb X-rays, while fluorinated compounds are often found in pharmaceuticals to improve the pharmacokinetics of drugs.

References

1964. Fluorinated diiodoalkanes and diolefins. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 13(2).
DOI: 10.1007/bf00853708

2010. Synthesis of 3,3,4,4-tetrafluoro-4-iodobutylamine, a bifunctional reagent for ionic and free-radical reactions. Russian Chemical Bulletin, 59(3).
DOI: 10.1007/s11172-010-0113-4