423-31-4

Usage

Uses

Used in Refrigeration Industry:
1-CHLORO-4H-OCTAFLUOROBUTANE is used as a refrigerant for its ability to provide efficient cooling in industrial and commercial cooling systems. Its low toxicity and non-flammability make it a preferred choice for these applications, ensuring safety and performance.
Used in Aerosol Products:
In the consumer goods industry, 1-CHLORO-4H-OCTAFLUOROBUTANE is utilized as a propellant in aerosol products. Its properties allow for the effective dispensing of substances in spray form, making it suitable for a range of products from personal care to household items.
Used as a Solvent:
1-CHLORO-4H-OCTAFLUOROBUTANE also finds use as a solvent in certain applications, where its chemical properties are beneficial for dissolving or suspending other substances in various processes.
Environmental Considerations:
Despite its wide range of applications, 1-CHLORO-4H-OCTAFLUOROBUTANE is recognized as a potent greenhouse gas. Its contribution to global warming has raised environmental concerns, prompting the search for alternative compounds that minimize climate impact while maintaining the performance characteristics required for these applications.

InChI:InChI=1/C4HClF8/c5-4(12,13)3(10,11)2(8,9)1(6)7/h1H

Upstream product

• 557-40-4 Allyl ether 
• 5848-38-4 1-chloro-4-iodo-1,1,2,2,3,3,4,4-octafluorobutane 
• 91-65-6 diethyl-cyclohexyl-amine 
• 14851-10-6 bis-ethoxycarbonyl-methanide 
• 141-97-9 ethyl acetoacetate 
• 121-69-7 N,N-dimethyl-aniline 
• 100-01-6 4-nitro-aniline 
• 149-30-4 2-Mercaptobenzothiazole 
• 100-61-8 N-methylaniline 
• 91-66-7 N,N-diethylaniline 
• 110-83-8 cyclohexene 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 

Downstream Products

• 57825-37-3 1,4-Dimethyl-2-(1,1,2,2,3,3,4,4-octafluoro-butyl)-benzene 
• 1310492-31-9 ethyl 2-(4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl)benzoate 

Relevant academic research and scientific papers

A general, regiospecific synthetic route to perfluoroalkylated arenes via arenediazonium salts with RFCu(CH3CN) complexes

A mild method of converting arylamines into perfluoroalkylated arenes is described. Relatively stable RFCu(CH3CN) complexes are used as perfluoroalkylating agents, which react smoothly with arenediazonium salts to produce various perfluoroalkylarenes in good yields. Based on the results of clock trapping experiments with diallyl ether, a radical process might be involved in the reaction.

Complexation and Photoinduced Electron-transfer Reaction between Perfluoroalkyl Iodides and N,N,N',N'-Tetramethylphenylene-1,4-diamine, Anilines and Piperazines

Treatment of tetrafluoro-1,2-diiodoethane 1a or dodecafluoro-1,6-diiodohexane 1b with N,N,N',N'-tetramethylphenylene-1,4-diamine 2 gave 1 + 1 solid complexes 3a or 3b in high yields.Complex 3a decomposed to give tetrafluoroethylene, iodine and 2 when irradiated with UV or heated.Complex 3b was converted into 6H-dodecafluorohexyl-N,N,N',N'-tetramethylphenylene-1,4-diamine 4 when irradiated with UV.On treatment of 1a and 1b with piperazine 6a and N,N'-dimethylpiperazine 6b, 1 + 1 solid complexes 7 were similarly obtained.However, heating or irradiating 7 gave no perfluoroalkylated products.Irradiating a mixture of 2 or anilines 13 and perfluoroalkyl iodides 10 in dimethylformamide also gave perfluoroalkylated products.The photoinduced electron transfer reaction involved radical cation 2*+ as a reactive intermediate which was detected by EPR techniques.

PERFLUOROALKYLATION OF 2-MERCAPTOBENZOTHIAZOLE AND ITS ANALOGUES WITH PERFLUOROALKYL IODIDES BY AN SRN1 REACTION

The thiolates, generated in situ by the reaction of 2-mercaptobenzothiazole (1) and its analogues (2) and (3) with sodium hydride, react under UV irradiation with perfluoroalkyl iodides (4)-(8) to give the corresponding heteroaromatic perfluoroalkyl sulfides (9)-(18) in 50-98percent yields.The fact that the UV irradiation increases the conversion of perfluoroalkyl iodides and that the radical scavenger di-tert-butylnitroxide suppresses the reaction demonstrates that the reaction proceeds via an SRN1 mechanism.

A FACILE METHOD FOR FLUOROALKYLATION OF ANILINE AND ITS DERIVATIVES

In the presence of tetrakis(triphenylphosphine)nickel, fluoroalkylation reactions of aniline and its derivatives occur under mild conditions, giving good yields of the corresponding o- and p-fluoroalkylaniline.The reaction shows regioselectivity.The hydrolytic behaviors of the products are also described.

STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION. PART 24. MAGNESIUM-INDUCED SINGLE ELECTRON TRANSFER IN REACTIONS OF FLUOROALKYL IODIDES WITH ALKENES AND ALKYNES

Magnesium metal catalyses the radical reactions of perfluoroalkyl iodides with alkenes and alkynes to give the corresponding adducts in high yields under mild conditions.The presence of 1,4-dinitrobenzene (p-DNB) or oxygen does not affect the reaction, bu

Nickel-, Palladium-, and Platinum-Catalyzed Reactions of Perfluoro- and Polyfluoroalkyl Iodides with Tertiary Amines

The relative catalytic activities of Ni group metals in the reactions of perfluoroalkyl and polyfluoroalkyl iodides with tertiary amines to give enamines were compared, giving a reactivity order Ni > Pd > Pt, which parallels the order of the first ionization potential of the three metals.In comparing the Ni-catalyzed reaction of iodide 1 with tertiary amines containing zero to three methyl groups, it was found that in the case of trimethylamine only the reduced product 4 was formed, while the other three types of tertiary amines produced enamines (19, 21, 23) as wellas 4.The chemoselectivity of this reaction was studied.A mechanism is proposed for the reaction.Acid hydrolysis of (fluoroalkyl)enamines afforded enaminones or aldehydes depending upon the presence or absence of an alkyl group at the β-carbon.

Studies on fluoroalkylation and fluoroalkoxylation. Part 10. Electron-transfer induced reactions of perfluoroalkyl iodides and the dialkyl malonate anion and β-fragmentation of the halotetrafluoroethyl radical

Fluoroalkyl iodides, XCF2CF2I (X=F, perfluoroalkyl group) (1), react readily with malonic ester anion (2) in DMF to give {A figure is presented} (3), 1-hydroperfluoroalkane (4) and dimer of the anion (5). The reaction is accelerated by UV irradiation and partly suppressed by p-DNB. Diallyl ether (DAE) can trap the radical intermediates to afford five-membered ring products. Interestingly, in the case of 1 ( X = Cl, I ) the same reaction mainly yielded tetrafluoroethylene and 5 instead of 3 and 4. The radical intermediate XCF2CF·2 ( X=Cl ) can also be trapped by DAE to yield tetrahydrofuran derivatives. All these results can be rationalized in terms of the SRN1 mechanism.

STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION. PART 3. PERFLUOROALKYLATION OF OLEFINS WITH PERFLUOROALKYLIODIDES AND COPPER IN VARIOUS SOLVENTS

Perfluoroalkyl iodides react readily with simple olefins in the presence of catalytic amounts of copper in diglyme or acetic anhydride to give adducts in high yields.The reaction can be moderately accelerated by irradiation, partily suppressed with p-DNB and inhibited completely by hydroquinone.Fluorine-containing non-volatile amorphous solids were obtained when easily polymerized olefins, such as styrene and acrylates, were used as substrates.The reaction of perfluoroalkyl iodides and diallylic ether gave five-membered ring products under the same conditions.All the results seem to indicate that the reaction is a radical chain process induced by electron transfer.In DMSO, the main reaction may involve perfluoroalkylcopper intermediates which can be trapped by iodobenzene and hydroquinone and p-DNB show little inhibition effects.