2681-00-7

Usage

Uses

Used in Chemical Synthesis:
1,8-DIIODO-3,3,4,4,5,5,6,6-OCTAFLUOROOCTANE is used as a starting material for the synthesis of various fluorinated compounds, leveraging its unique properties to create new chemical entities with specific applications.
Used in Organic Chemistry Reactions:
In the field of organic chemistry, 1,8-DIIODO-3,3,4,4,5,5,6,6-OCTAFLUOROOCTANE serves as a reagent, facilitating specific reactions that require its unique chemical characteristics.
Used in Industrial Applications:
1,8-DIIODO-3,3,4,4,5,5,6,6-OCTAFLUOROOCTANE is used as a high-temperature lubricant and heat transfer fluid in various industrial processes. Its non-reactive and stable nature makes it suitable for applications where such properties are crucial.
Used in Environmental and Health Considerations:
While 1,8-DIIODO-3,3,4,4,5,5,6,6-OCTAFLUOROOCTANE has various industrial uses, it is also recognized as a persistent environmental pollutant and potential health hazard. As a result, it is used in research and regulatory efforts to understand its impact and find more sustainable alternatives to mitigate its accumulation in the environment and potential bioaccumulation in organisms.

InChI:InChI=1/C8H8F8I2/c9-5(10,1-3-17)7(13,14)8(15,16)6(11,12)2-4-18/h1-4H2

Upstream product

• 74-85-1 ethene 
• 375-50-8 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane 

Downstream Products

• 678-65-9 3,3,4,4,5,5,6,6-octafluoro-1,7-octadiene 
• 132833-42-2 1,8-diazido-3,3,4,4,5,5,6,6-octafluorooctane 
• 83192-87-4 3,3,4,4,5,5,6,6-octafluoro-1,8-octanediol 
• 336-08-3 perfluoroadipic acid 
• 132942-76-8 C₄₄H₃₈F₈N₂P₂ 

Relevant academic research and scientific papers

PARTIALLY FLUORINATED SULFINIC ACID MONOMERS AND THEIR SALTS

Described herein is a composition according to formula I or its precursor, formula II: CX1X3=CX2-(R1)p-CZ1 Z2-SO2M (I) wherein X1, X2, and X3 are independently selected from H, F, Cl, Br, I, CF3 and CH3, and wherein at least one of X1, X2, or X3 is a H; R1 is a linking group; Z1 and Z2 are independently selected from F, Cl, Br, I, CF3, and a perfluoroalkyl group; p is 0 or 1; and M is a cation; and CX4X1X3-CX5X2-(R1)p-CZ1Z2-SO2M (II) wherein X1, X2, and X3 are independently selected from H, F, Cl, Br, I, CF3 and CH3, wherein at least one of X1, X2, or X3 is a H, and X4 and X5 are independently selected from H, F, Cl, Br and I; R1 is a linking group; Z1 and Z2 are independently selected from F, Cl, Br, I, CF3, and a perfluoroalkyl group, p is 0 or 1; and M is selected from F, and a cation.

Synthesis of telechelic dienes from fluorinated α,ω-diiodoalkanes. Part I. Divinyl and diallyl derivatives from model I(C2F4)nI compounds

The synthesis of five fluorinated non-conjugated dienes from commercially available α,ω-diiodoperfluoroalkanes is described.Preparation of the fluorinated divinyl derivatives H2C=CH(CF2)nCH=CH2 (n = 2, 4, 6) (2,2, 2,4 and 2,6) was effected by ethylenation of these diiodinated compounds in various ways followed by dehydroiodination in ethanolic potassium hydroxide.Allyl diolefines, H2C=CHCH2(CF2)nCH2CH=CH2 (4,4 and 4,6) were produced by the α,ω-bis-telomerization of allyl acetate followed by deiodoacetoxylation in the presence of zinc.The diacetate precursors 3,4 and 3,6 of the respective diallyls 4,4 and 4,6 were obtained rather than diacetate 3,2 because of the eventual decomposition of α,ω-diiodoperfluoroethane by β-scission.These five fluorinated non-conjugated dienes have been characterized by 1H, 13C and 19F NMR spectroscopy. - Keywords:Telechelic dienes; Fluorinated vinyl dienes; Fluorinated allyl dienes; α,ω-Diiodoperfluoroalkanes; NMR spectroscopy

Fluorine-containing α,β-bifunctional compounds and process for their production

A fluorine-containing α,ω-bifunctional compound having the formula: STR1 wherein each of R1 and R2 independently is a hydrogen atom, an alkyl group or an aralkyl group; X is --COOH, --COOR3, --COY or --NCO, wherein R3 is an alkyl group or an aralkyl group and Y is a halogen atom or N3 ; and n is an integer of at least 1 provided that when X is --COOH, n is an integer of at least 4.

SYNTHESIS OF FLUORINE-CONTAINING NITRO COMPOUNDS

Fluoronitro alkanes (5a and 5b), possesing the structure -CF2CH2CH(NO2)2, were synthesized from 1-iodo-1H,1H,2H,2H-perfluoroalkanes by displacing the iodide with sodium nitrite and then oxidatively nitrating the 1-nitro-1H,1H,2H,2H-perfluoroalkanes with tetranitromathane.Reaction with formaldehyde gave the dinitroalcohols, 6a and 6b. α,ο-diiodoperfluoroalkames (1c and 1d) were similarly converted to tetranitrofluoroalkanes (5c and 5d), characterized as tetranitrodiols 6c and 6d, and Michael adducts with methyl acrylate, 7c and 7d.

SYNTHESIS OF FLUORINATED DIFUNCTIONAL MONOMERS

In order to obtain fluorinated difunctional monomers for fluoropolyurethanes, we synthesized novel fluorinated aliphatic diisocyanates (OCNCH2(CF2)nCH2NCO) from corresponding diols (HOCH2CH2(CF2)nCH2CH2OH).Oxidation of the diols with chromium trioxide-sulfuric acid gave α,α,ω,ω-tetrahydroperfluoroalkylene dicarboxylic acids in high yields.Then treating the acids with phosphorus pentachloride afforded corresponding dicarboxyl chlorides, which are easily converted to dicarboxyl azides with hydrazoic acid-pyridine complex.Finally, on Curtius rearrangement of the azides, the end products, α,α,ω,ω-tetrahydroperfluoroalkylene diisocyanates were obtained in 53percent (n=4) and 19percent (n=6) yields from the starting diols.

Synthesis of Fluorinated Acetylenes

New routes to fluorinated acetylenes were developed on the basis of additions of iodofluorocarbons to silylacetylenes.Free radical addition of α,ω-diiodoperfluoroalkanes to (trimethylsilyl)acetylene gave the iodotrimethylsilyl olefins Me3SiIC=CH(CF2)nCH=CISiMe3, which reacted with potassium tert-butoxide or DBU to give the (trimethylsilyl)acetylenes and, with an excess of the base, the free diacetylenes.Perfluoroalkyl iodides similarly gave (perfluoroalkyl)acetylenes.The addition of perfluoroheptyl iodide to phenylacetylene, followed by treatment with potassium tert-butoxide gave 1-phenylperfluorononyne.The peroxide-catalyzed reactionof perfluoroalkyl iodides and bis(trimethylsilyl)acetylene gave 1:1 adducts, RF(Me2SiCH2I)C=CHSiMe3, resulting from intramolecular hydrogen abstraction by the initially formed vinyl radical.However, the thermal reaction of perfluoroalkyl iodides and diiodides with bis(trimethylsilyl)acetylene in the presence of free iodine gave the (trimethylsilyl)acetylenes, which were desilylated with potassium fluoride.A route to diacetylenes was investigated on the basis of addition of perfluoroiodo compounds to ethylene, dehydroiodination, brominations, and eliminations.