356-18-3

Basic information

• Product Name: 1,2-DICHLOROHEXAFLUOROCYCLOBUTANE
• Synonyms: FC-C-316;HEXAFLUORO-1,2-DICHLOROCYCLOBUTANE;1,2-DICHLOROHEXAFLUOROCYCLOBUTANE;1,2-Dichloro-1,2,3,3,4,4-hexafluorocyclobutane;1,2-dichlorohexafluoro-cyclobutan;1,2-Dichloroperfluorocyclobutane;Cyclobutane, 1,2-dichlorohexafluoro-;1,2-Dichlorohexafluorocyclobutane97%
• CAS NO: 356-18-3
• Molecular Formula: C₄Cl₂F₆
• Molecular Weight: 232.94
• EINECS: 206-599-7
• Product Categories: refrigerants
• Mol File: 356-18-3.mol

Chemical Properties

• Melting Point: -15 °C
• Boiling Point: 59 °C
• Flash Point: 59-60°C
• Appearance: /
• Density: 1.644
• Vapor Pressure: 213mmHg at 25°C
• Refractive Index: 1.333
• BRN: 1909267
• CAS DataBase Reference: 1,2-DICHLOROHEXAFLUOROCYCLOBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DICHLOROHEXAFLUOROCYCLOBUTANE(356-18-3)
• EPA Substance Registry System: 1,2-DICHLOROHEXAFLUOROCYCLOBUTANE(356-18-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• RTECS: GU1760000
• HazardClass: IRRITANT
• Hazardous Substances Data: 356-18-3(Hazardous Substances Data)

Usage

Uses

Used in Refrigeration Industry:
1,2-Dichlorohexafluorocyclobutane is used as a refrigerant for its low environmental impact, serving in applications such as air conditioning and heat pumps. Its low global warming and ozone depletion potentials make it a preferred choice over other refrigerants that contribute more significantly to climate change.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 1,2-Dichlorohexafluorocyclobutane is utilized as a solvent, playing a crucial role in the production process of various medications. Its unique properties allow for the efficient synthesis of complex drug molecules.
Used in Electronics Industry:
1,2-Dichlorohexafluorocyclobutane also serves as a solvent in the manufacturing of electronic components, where its chemical stability and properties are beneficial for the production of high-quality electronic devices.
Used in Insulation Materials Production:
As a blowing agent, 1,2-Dichlorohexafluorocyclobutane is employed in the creation of insulating foam materials, enhancing the thermal insulation properties of these products.
Despite its various applications, the use of 1,2-Dichlorohexafluorocyclobutane is declining due to growing environmental concerns and the push for more sustainable alternatives to mitigate its potential long-term impact on climate change.

InChI:InChI=1/C4Cl2F6/c5-1(7)2(6,8)4(11,12)3(1,9)10

Upstream product

• 79-38-9 Chlorotrifluoroethylene 
• 684-16-2 Hexafluoroacetone 
• 357-21-1 3,4-dichlorohexafluoro-1-butene 
• 697-11-0 hexafluorocyclobut-1-ene 
• 7782-50-5 chlorine 
• 343777-24-2 3,4-dichlorohexafluorotetrahydrothiophene 1,1-dioxide 

Downstream Products

• 22819-47-2 cis-1,1,2,2,3,4-hexafluorocyclobutane 
• 377-95-7 trans-1,2-dihydrohexafluorocyclobutane 
• 697-11-0 hexafluorocyclobut-1-ene 
• 79-38-9 Chlorotrifluoroethylene 

Relevant articles and documents

A New Synthesis of Fluorinated Oxetanes

Polyfluorinated oxetanes are prepared in high yields by an electrophilic cycloaddition reaction between hexafluoroacetone and fluorinated ethylenes that is catalyzed by an anhydrous aluminum chlorofluoride Lewis acid.The reaction is regiospecific with hydrofluoroethylenes CHX=CF2 (X = H, F, Cl, Br), whereas halotrifluoroethylenes CFX=CF2 (X = Cl, Br) give nearly equal amounts of the isomeric oxetanes.Hexafluoropropylene oxide, which rapidly rearranges under the reaction conditions, can be substituted for hexafluoroacetone in this new oxetane synthesis.

Structural assignment of fluorocyclobutenes by19F NMR spectroscopy – Comparison of calculated19F NMR shielding constants with experimental19F NMR shifts

Although the optimized reduction of perfluorocyclo-butene with LiAlH4 gave a quantitative yield of the target 3,3,4,4-tetrafluorocyclobut-1-ene, unoptimized reductions led to complex inseparable mixtures of fluorocyclobutenes. These mixtures showed highly complex19F NMR spectra, the assignment of which was quite tedious. Hence, we accomplished a series of single-reference computations of the19F NMR magnetic shieldings of the corresponding fluorine atoms. Surprisingly, various DFT approaches, including both traditional and advanced functionals, gave highly diverse results with poor correlations between the experimental and computed19F chemical shifts, and the individual fluorocyclobutenes could not be identified. In contrast, the domain-based local pair natural orbital coupled clusters (DLPNO-CCSD) method, developed recently as a part of the ORCA computational package, gave shielding values that enabled the assignment of all structures observed, albeit with some systematic errors. Slightly better magnetic shielding values were obtained by a simple Hartree–Fock (HF) method with a specially tailored IGLO-III basis set. The method developed was successfully employed for the assignment of the19F NMR shifts of unknown fluorocyclobutenes.

Bimolecular kinetic studies with high-temperature gas-phase 19F NMR: Cycloaddition reactions of fluoroolefins

A gas-phase NMR kinetic technique has been used for the first time to obtain accurate measurements of rate constants of some bimolecular, second-order cycloaddition reactions. As a test of the potential use of this technique for the study of second-order reactions, the rate constants and the activation parameters for the cyclodimerization reactions of chlorotrifluoroethylene (CTFE) and tetrafluoroethylene (TFE) were determined in the temperature range 240-340 °C, using a commercial high-temperature NMR probe. Obtaining excellent agreement of the results with published data, the technique was then applied to the reaction of 1,1-difluoroallene with 1,3-butadiene, the results of which indicate that the use of gas-phase NMR for reaction kinetics is particularly valuable when a reagent is available only in small amounts and in cases where there are several competing processes occurring simultaneously. The major processes observed in this reaction are regioselective [2+2] and [2+4] cycloadditions, whose rates and activation parameters were determined [k2=9.3×106 exp(-20.1 kcal mol-1/RT) L/mol-1 S-1 and k3=1.2×106 exp(- 18.4 kcal mol-1/RT) L/mol-1 S-1, respectively] in the temperature range 130-210 °C.

Syntheses with Halogen Derivatives of Thiophene and Benzothiophene

Pyrolysis of octachlorotetrahydrothiophene 1,1-dioxide provides a practical synthesis of octachlorocyclobutane. 1,2-Dichlorohexafluorotetrahydrothiophene 1,1-dioxide also yields a cyclobutane.Treatment of these sulfones with potassium hydroxide forms perhalogenated 3-butenesulfonates.From octachloro-2,3-dihydrobenzothiophene 1,1-dioxide, octachlorostyrene is produced by pyrolysis and hexachlorobenzothiophene 1,1-dioxide by treatment with sodium iodide.Hexachlorobenzothiophene has been prepared from octachloro-2,3-dihydrobenzothiophene and oxidized with chromium trioxide to a thiolactone (17).Hydrolysis of the latter gives a 2H-benzothiete (18).Oxidation of tetrachlorothiophene forms the thiolactone tetrachloro-2,3-dihydrothiophen-2-one (19).Octachlorodibenzothiophene can be made by direct chlorination.