2043-57-4

Basic information

• Product Name: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane
• Synonyms: 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodo-octan;1,1,2,2-Tetrahydroperfluorooctyliodide;2-Perfluorohexyl-1-iodoethane;2-(PERFLUOROHEXYL)ETHYL IODIDE;3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO-1-IODOOCTANE;3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUOROOCTYL IODIDE;1,1,1,2,2,3,3,4,4,5,5,6,6-TRIDECAFLUORO-8-IODOOCTANE;1-IODO-1H,1H,2H,2H-PERFLUOROOCTANE
• CAS NO: 2043-57-4
• Molecular Formula: C₈H₄F₁₃I
• Molecular Weight: 474
• EINECS: 218-056-1
• Mol File: 2043-57-4.mol

Chemical Properties

• Melting Point: 21 °C
• Boiling Point: 92 °C45 mm Hg(lit.)
• Flash Point: 177 °F
• Appearance: Clear/Liquid
• Density: 1.934 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.29mmHg at 25°C
• Refractive Index: n20/D 1.359(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Soluble), Methanol (Slightly)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• Stability: Volatile
• BRN: 1887105
• CAS DataBase Reference: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane(2043-57-4)
• EPA Substance Registry System: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane(2043-57-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 8
• TSCA: T
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 2043-57-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane is used as an intermediate in the synthesis of organic fluoride products for various applications. Its unique structure allows for the formation of a wide range of fluorinated compounds with diverse properties and potential uses in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane is used as a building block for the development of new drugs with improved properties. Its fluorinated nature can enhance the stability, solubility, and bioavailability of drug molecules, leading to more effective therapeutic agents.
Used in Chemical Research:
1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane is also used in chemical research as a model compound to study the properties and behavior of polyfluorinated compounds. This can help in understanding the fundamental aspects of fluorine chemistry and its applications in various fields.
Used in Environmental Applications:
Due to its potential estrogenic effects, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane can be used in environmental studies to understand the impact of polyfluorinated compounds on the endocrine system and develop strategies for mitigating their effects on ecosystems.

InChI:InChI=1/C8H4F13I/c9-3(10,1-2-22)4(11,12)5(13,14)6(15,16)7(17,18)8(19,20)21/h1-2H2

Upstream product

• 74-85-1 ethene 
• 355-43-1 n-perfluorohexyl iodide 
• 74-95-3 1,1-dibromomethane 
• 647-42-7 1H,1H,2H,2H-tridecafluoro-n-octanol 
• 507-63-1 1-iodoheptadecafluorooctane 
• 307-60-8 1-iodoperfluorododecane 
• 423-62-1 1-Iodo-perfluorodecane 

Downstream Products

• 26650-09-9 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl thiocyanate 
• 25291-17-2 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene 
• 647-42-7 1H,1H,2H,2H-tridecafluoro-n-octanol 
• 78522-69-7 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl trifluoromethanesulfonate 
• 27854-30-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoic acid 
• 80793-17-5 (perfluoro-n-hexyl)ethane 
• 34451-26-8 2-perfluorohexylethanethiol 
• 76598-01-1 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl magnesium iodide 
• 103249-38-3 tris(1H,1H,2H,2H-perfluorooctyl)phosphine 
• 51066-74-1 dimethylamine hydriodide 
• 87851-83-0 benzyl(F-hexyl-2 ethyl) sulfure 
• 94190-73-5 (1H,1H,2H,2H-perfluorooctyl)triphenylphosphonium iodide 
• 7060-52-8 1-(1-pyrrolin-2-yl)-2-pyrrolidinone 

Relevant articles and documents

Novel fluorinated amphiphilic cyclodextrin derivatives: Synthesis of mono-, di- and heptakis-(6-deoxy-6-perfluoroalkylthio)-β-cyclodextrins

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Synthesis and surface properties of a series of surfactants based on O-alkyl and O-perfluoro-N,N′-diisopropylisoureas

O-Dodecyl-N,N′-diisopropylisourea and O-tridecafluorooctyl-N, N′-diisopropylisourea were synthesized by reaction of hydrogenated or fluorinated alcohols onto diisopropylcarbodiimide in quasi-quantitative yields. Adding various hydrogen halides (HCl, HBr, or HI) onto these isoureas enabled one to obtain isoureas hydrohalides with tensioactive properties. The surface properties of both series of hydrogenated and fluorinated surfactants were studied and compared. The influence of the counter-ions onto the surface properties showed that the tensioactive properties were improved in the following increasing order: I Cl Br. Fluorinated isourea hydrohalides exhibited better surfactant properties than their hydrogenated homologues.

Synthesis of perfluoroalkyl-containing multifunctional groups compounds for textile finishing

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Copper-Catalyzed Difluoromethylation of Alkyl Iodides Enabled by Aryl Radical Activation of Carbon–Iodine Bonds

The engagement of unactivated alkyl halides in copper-catalyzed cross-coupling reactions has been historically challenging, due to their low reduction potential and the slow oxidative addition of copper(I) catalysts. In this work, we report a novel strategy that leverages the halogen abstraction ability of aryl radicals, thereby engaging a diverse range of alkyl iodides in copper-catalyzed Negishi-type cross-coupling reactions at room temperature. Specifically, aryl radicals generated via copper catalysis efficiently initiate the cleavage of the carbon–iodide bonds of alkyl iodides. The alkyl radicals thus generated enter the copper catalytic cycles to couple with a difluoromethyl zinc reagent, thus furnishing the alkyl difluoromethane products. This unprecedented Negishi-type difluoromethylation approach has been applied to the late-stage modification of densely functionalized pharmaceutical agents and natural products.

Environmentally friendly preparation method of fluorine-containing acrylate

The invention relates to the technical field of preparation of new fluorine-containing materials, particularly to an environmentally friendly preparation method of fluorine-containing acrylate. The environmentally friendly preparation method comprises: carrying out a reaction on short-chain perfluoroiodoalkane and ethylene, separating, and purifying to obtain perfluoroalkylethyl iodide; carrying out hydrolysis on the perfluoroalkylethyl iodide, separating, and purifying to obtain perfluoroalkylethanol; and carrying out a reaction on the perfluoroalkylethanol and acrylic acid, separating, and purifying to obtain the product. According to the present invention, the perfluorooctyl-free product is synthesized, the potential risk of PFOA production cannot exist, and the obtained product is theenvironmentally friendly product, and meets the national industrial policy; the preparation method is simple, and is suitable for industrial production; and the reaction conversion rate is high, and the purity of the intermediate product is high, such that the subsequent reaction is easily performed, the yield is easily increased, and the cost is reduced.

Fluorinated pyridinium and ammonium cationic surfactants

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A fluoroelastomer that bears pendant nitrile groups is crosslinked with a telechelic bis-azido fluorinated curing agent by "click" azide-nitrile cycloaddition. Thermogravimetric analyses of the resulting press cured films reveal an improvement by 20 C of the thermal degradation profile under air, compared to that of the corresponding uncured fluoroelastomer.

PROCESS FOR PRODUCING FLUORINATED ACRYLIC ESTER

A mixture of fluorine-containing acrylic esters represented by CF3(CF2)nCH2CH2OCOCR1=CH2 wherein R1 is a hydrogen atom, a methyl group or a halogen atom and "n" is an integer of at least zero is subjected to distillation under such conditions that the esters are not polymerized, so as to give a mixture of the esters with a less content of impurities (that is, olefins represented by CF3(CF2)nCH=CH2 and alcohols represented by CF3(CF2)nCH2CH2OH) at a high yield.

Purification of fluorinated alcohols

A process for reducing the level of perfluoroalkanoic acids, perfluoroalkanoic esters, and perfluoroalkyliodides in fluorinated alcohols comprising heating a fluorinated alcohol, or mixtures thereof, containing said acids, esters, or iodides to a temperature of at least 175° C. in the presence of water and a base additive is disclosed.

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