Hexafluoro-1,3-butadiene
[CAS# 685-63-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: Hexafluoro-1,3-butadiene
• Synonyms: 1,1,2,3,4,4-Hexafluorobuta-1,3-diene
• Molecular Formula: C₄F₆
• Molecular Weight: 162.03
• CAS Registry Number: 685-63-2
• EC Number: 211-681-0
• SMILES: C(=C(F)F)(C(=C(F)F)F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.553 g/mL (Expl.)
• Melting point: -132 °C (Expl.)
• Index of Refraction: 1.297, Calc.^*, 1.378 (Expl.)
• Boiling Point: 18.6±35.0 °C (760 mmHg), Calc.^*, 6 °C (Expl.)
• Flash Point: -17.2±17.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS04;GHS06 Danger
• Risk Statements: H220-H280-H331
• Safety Statements: P203-P210-P222-P261-P271-P280-P304+P340-P316-P321-P377-P381-P403-P403+P233-P405-P410+P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable gases	Flam. Gas	1	H220
Acute toxicity	Acute Tox.	3	H331
Gases under pressure (liquid)	Press. Gas (Liq.)		H280
Gases under pressure (compressed)	Press. Gas (Comp.)		H280
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	2	H330

Discovery and Applications

Hexafluoro-1,3-butadiene, with the chemical formula C₄HF₆, is a fluorinated organic compound characterized by a conjugated diene structure with six fluorine atoms attached to the carbon backbone. This compound is a member of the class of perfluorinated hydrocarbons and is known for its unique chemical and physical properties, which make it useful in various applications in the chemical and materials industries.

The discovery of hexafluoro-1,3-butadiene dates back to the mid-20th century, when researchers began investigating the reactivity and properties of fluorinated compounds. As an unsaturated compound with a diene structure, hexafluoro-1,3-butadiene was synthesized in the laboratory through the introduction of fluorine atoms into the butadiene molecule. The development of hexafluoro-1,3-butadiene was part of a broader effort to explore the potential applications of fluorinated organic compounds, especially those with unusual reactivity and stability characteristics.

Hexafluoro-1,3-butadiene is primarily used as a monomer in the production of specialty polymers. Its fluorine content imparts a high level of chemical stability, making it an ideal candidate for creating polymers that are resistant to harsh chemical environments, high temperatures, and radiation. The polymerization of hexafluoro-1,3-butadiene leads to the formation of perfluorinated polymer materials, which are highly resistant to solvents, acids, and bases. These polymers are used in a variety of high-performance applications, including coatings, seals, gaskets, and membranes in industries such as aerospace, electronics, and chemical processing.

One of the key applications of hexafluoro-1,3-butadiene and its derived polymers is in the field of insulation materials. The high chemical stability and low dielectric constant of fluorinated polymers make them well-suited for use as insulating materials in electrical cables, electronic devices, and other equipment where protection from environmental factors such as moisture and chemicals is crucial. The polymers derived from hexafluoro-1,3-butadiene can withstand extreme temperatures and harsh chemical environments, ensuring the longevity and reliability of electronic systems and components.

In addition to its use in polymer synthesis, hexafluoro-1,3-butadiene is employed in the development of high-performance materials for the semiconductor industry. The compound can be used as a precursor to fluorinated thin films and coatings, which are critical in the fabrication of semiconductors and microelectronic devices. These fluorinated materials offer superior thermal stability and resistance to corrosion, making them suitable for use in the harsh conditions encountered during the manufacturing of semiconductors.

Hexafluoro-1,3-butadiene also plays a role in the production of specialty chemicals. It can be used as a building block in the synthesis of other fluorinated compounds, which have applications in pharmaceuticals, agrochemicals, and other chemical industries. The presence of fluorine in the molecule enhances the chemical stability and bioactivity of the resulting compounds, making them valuable in various formulations.

The compound's chemical structure, with its conjugated diene and fluorine atoms, also makes it an attractive candidate for use in the development of new materials with unique electronic and optical properties. Research into the properties of hexafluoro-1,3-butadiene and similar compounds continues, with ongoing studies focusing on their potential applications in advanced materials for electronic devices, photonic systems, and other high-tech applications.

Overall, hexafluoro-1,3-butadiene is an important fluorinated compound with diverse applications in the production of specialty polymers, materials, and chemicals. Its unique chemical properties, including high chemical stability, resistance to harsh environments, and suitability for use in advanced materials, make it a valuable substance in a wide range of industrial sectors. The continued development of its applications reflects its role in meeting the demands of industries requiring materials that can withstand extreme conditions.

References

2022. A DFT Study on the Direct CF2 Fragmentation Mechanisms of 1,3-C4F6 and 1,3-C4F6+ in Plasma. Plasma Chemistry and Plasma Processing, 42(6).
DOI: 10.1007/s11090-022-10288-6

2014. Explosion characteristics of hexafluorobutadiene. Russian Journal of Physical Chemistry B, 8(6).
DOI: 10.1134/s1990793114110220

2010. Experimental Study of Capacitive RF c-C4F8 Discharge with Synchrotron Vacuum Ultraviolet Photoionization Mass Spectrometry. Plasma Chemistry and Plasma Processing, 30(3-4).
DOI: 10.1007/s11090-010-9230-y