375-50-8

Basic information

• Product Name: 1,4-DIIODOOCTAFLUOROBUTANE
• Synonyms: Octafluorotetramethylene diiodide;1,4-Diiodooctafluo;1,4-Diiodoperfluorobutane 98%;1,4-Diiodooctafluorobutane, 97%, stab. with copper;1,4-Diiodoperfluorobutane, 1,4-Diiodo-1,1,2,2,3,3,4,4-octafluorobutane;1,4-Diiodooctafluorobutane, stabilized with copper;1,4-DIIODOPERFLUOROBUTANE;1,4-DIIODOOCTAFLUOROBUTANE
• CAS NO: 375-50-8
• Molecular Formula: C₄F₈I₂
• Molecular Weight: 453.84
• EINECS: 206-788-4
• Product Categories: Synthetic Organic Chemistry;Alkyl;Halogenated Hydrocarbons;Organic Building Blocks;Fluorous Chemistry;Fluorous Compounds
• Mol File: 375-50-8.mol

Chemical Properties

• Melting Point: −9 °C(lit.)
• Boiling Point: 150 °C(lit.)
• Flash Point: 85°C/100mm
• Appearance: Clear colorless to light yellow or pink/Liquid
• Density: 2.474 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.02mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Hexane (Slightly)
• Water Solubility: 9.3mg/L at 20℃
• Sensitive: Light Sensitive
• Stability: Stable, but light sensitive. Incompatible with active metals, strong oxidants.
• BRN: 1777548
• CAS DataBase Reference: 1,4-DIIODOOCTAFLUOROBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIIODOOCTAFLUOROBUTANE(375-50-8)
• EPA Substance Registry System: 1,4-DIIODOOCTAFLUOROBUTANE(375-50-8)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: TOXIC
• Hazardous Substances Data: 375-50-8(Hazardous Substances Data)

Usage

Uses

1. Used in Polymer Production:
1,4-Diiodooctafluorobutane is used as a chain transfer agent in the method for producing fluoropolymers, specifically perfluoroelastomers. Its role in the production process helps to control the molecular weight and architecture of the resulting polymers, which are essential for their performance characteristics in various applications.
2. Used in Nuclear Industry:
In the nuclear industry, 1,4-Diiodooctafluorobutane is utilized as a component in the formation of a "binary host" system when combined with a calixcrown compound. This system is employed for the isolation of cesium iodide from aqueous to fluorous phase, which is crucial for nuclear waste management and the safe handling of radioactive materials.
3. Used in Chemical Research:
Due to its unique chemical properties as a halogen bond donor, 1,4-Diiodooctafluorobutane is also used in chemical research to study cocrystallization with other compounds, such as MDPPO. This research can lead to a better understanding of the compound's properties and potential applications in various fields.

InChI:InChI=1/C4F8I2/c5-1(6,3(9,10)13)2(7,8)4(11,12)14

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 75-38-7 Vinylidene fluoride 
• 354-65-4 1,2-diiodotetrafluoroethane 

Downstream Products

• 5171-80-2 1,1,2,2,3,3,4,4-Octafluor-1,4-diphenyl-butan 
• 721-45-9 1,4-dimethyl-2-(4-methylbenzyl)benzene 
• 57825-37-3 1,4-Dimethyl-2-(1,1,2,2,3,3,4,4-octafluoro-butyl)-benzene 
• 2681-00-7 1,8-diiodo-3,3,4,4,5,5,6,6-octafluorooctane 
• 375-80-4 dodecafluoro-1,6-diiodohexane 
• 307-99-3 1H,8H-perfluorooctane 
• 335-70-6 1,8-diiodoperfluorooctane 
• 72049-11-7 1,12-diiodoperfluorododecane 
• 79162-64-4 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-Hexadecafluoro-1-iodo-octane 
• 87-68-3 Hexachlorobutadiene 
• 375-49-5 1,1,1,4,4,4-hexachloro-2,2,3,3-tetrafluoro-butane 
• 865-84-9 1H,12H-tetracosafluoro-dodecane 
• 78522-71-1 1,4-bis(fluorosulfonyloxy)octafluorobutane 
• 26206-34-8 1,4-Bis-(phenylthio)-perfluorbutan 

Relevant articles and documents

Preparation and characterization of a halogen-bonded shape-persistent chiral alleno-acetylenic inclusion complex

A chiral bidentate inclusion complex has been formed by halogen-bond interaction between the pyridyl moieties of a pyridoallenoacetylenic host and octafluorodiiodobutane. X-ray crystallography showed that the guest adopts a chiral conformation inside the molecular channels formed by stacking of the host units. A 10 ppm shielding of the 15N NMR resonance for the pyridil units provided evidence of the formation of the halogen-bond complex in solution.

Synthesis of fluorinated telomers. Part 4. Telomerization of vinylidene fluoride with commercially available α,ω-diiodoperfluoroalkanes

The synthesis of a new fluorinated α,ω-diiodo telomer I x(VDF)y)>I (A), where TFE and VDF represent tetrafluoroethylene and vinylidene fluoride respectively, has been carried out by telomerization of VDF with α,ω-diiodoperfluoroalkanes.The thermal telomerization of VDF with 1,2-diiodoperfluoroethane IC2F4I led to good yields of the monoadduct IC2F4CH2CF2I and of the diadduct which was composed of an almost equimolar ratio of ICF2CH2C2F4CH2CF2I and IC2F4(CH2CF2)2I, together with a small amount of IC2F4CH2CF2CF2CH2I and a triadduct containing I(VDF)C2F4(VDF)2I and IC2F4(VDF)3I.This procedure has been applied successfully to α,ω-diiodo-n-perfluorobutane and α,ω-diiodo-n-perfluorohexane.The reactivity of VDF relative to the fluorinated α,ω-diiodo telogens has been studied from which it is shown that the environment of the terminal group of the telogen is a major factor affecting the reactivity. - Keywords: Telomerization; Vinylidene fluoride; Thermal initiation; Diiodoperfluoroalkane; NMR spectroscopy; Mass spectrometry

Fluorine-containing compound, and its manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: perfluoroalkyl group CF2 groups of 4, 5 or 6 of this compound, a water and oil repellent, mold release agent and an active component of a surface treatment such as a resin or elastomer-like shaped when manufacturing a fluorine-containing polymer, which is effectively used as a polymerizable monomer, a fluorine-containing compound, and a manufacturing method thereof. SOLUTION: the [...]fluorine, vinylidene fluoride n under heating in the presence of or after the reaction, the reaction of a basic compound, fluorine-containing olefin compound is used. Selected drawing: no (by machine translation)

PARTIALLY FLUORINATED COMPOUNDS

Described herein is a composition comprising a partially fluorinated compound selected from the group consisting of: (a) I(CF2)XCH2CF2I; (b) ICF2CH2(CF2)XCH2CF2I; (c) I(CF2)yCH=CF2; (d) CF2=CH(CF2)yCH2CF2I; and (e) CF2=CH(CF2)yCH=CF2 wherein x is an odd integer selected from 3 to 11, and y is an integer greater than 2, along with methods of making and polymerizing such compounds.

PROCESS FOR THE PURIFICATION OF ALPHA, OMEGA-DIIODOPERFLUORINATED COMPOUNDS

The invention concerns a process for purifying α,ω-diiodoperfluorinated compounds of formula 1-(CF2CF2Y)m—I comprising contacting an impure α,ω-diiodoperfluorinated compound with a suitable sequestering agent, with formation of a reversible adduct and separating the α,ω-diiodoperfluorinated compound from the adduct itself. Diammonium dihalogenids of the general formula [R1,2,3N—(CH2)n—NR4,5,6]2*2X (R1-6=alkyl C1-C6n=8-26, X═I, Br, Cl) also called ‘methonium compounds’ are the preferred sequestering agents.

PROCESS FOR THE PURIFICATION OF ALPHA,OMEGA-DIIODOPERFLUORINATED COMPOUNDS

The invention concerns a process for purifying α,ω-diiodoperfluorinated compounds of formula I-(CF2CF2Y)m-I comprising contacting an impure α,ω-diiodoperfluorinated compound with a suitable sequestering agent, with formation of a reversible adduct and separating the α,ω-diiodoperfluorinated compound from the adduct itself. The invention also concerns α,ω-diiodoperfluorinated compounds of formula I-(CF2CF2Y)m-I wherein m is 5 to 10 and having 100% purity grades.

Practical and efficient synthesis of perfluoroalkyl iodides from perfluoroalkyl chlorides via modified sulfinatodehalogenation

A novel two-step one pot synthesis of perfluoroalkyl iodides (α,ω-diiodoperfluoroalkanes) from perfluoroalkyl chlorides (α-chloro-ω-iodoperfluoroalkanes) has been developed by initial conversion to the corresponding sodium perfluoroalkanesulfinates with sodium dithionite and then subsequent oxidation by iodine.

Process for manufacturing diiodoperfluoroalkanes

The present invention involves a process for the manufacture of α,ω-diiodoperfluoroalkanes of the formula I ― (CF2CF2)n ― I, wherein n is an integer between 2 and 6. The latter compounds are produced at relatively high conversions and under relatively mild reaction temperatures and pressures, compared to prior art processes, by the elimination of the gaseous byproduct perfluorocyclobutane throughout the process.

RELATIONSHIPS IN THE IODOFLUORINATION OF FLUOROOLEFINS IN THE IODINE-IODINE PENTAFLUORIDE-METAL FLUORIDE SYSTEM

On the basis of the results from investigation of the reaction of fluoroolefins with the components of the iodine-iodine pentafluoride-metal fluoride iodofluorinating system and kinetic and spectroscopic investigations a mechanism is proposed for the iodofluorination of fluoroolefins as the conjugate addition of iodine and fluorine with initial electrophilic attack on the multiple bond by the I2+ cation.The role of mass exchange during synthesis in a flow-type system is noted.

TELOMERIZATION OF TETRAFLUOROETHYLENE AND HEXAFLUOROPROPENE: SYNTHESIS OF DIIODOPERFLUOROALKANES

Linear diiodoperfluoroalkanes are easily synthesized by thermal telomerization of tetrafluoroethylene with iodine.When hexafluoropropene reacts with I(C2F4)nI n = 2,3,4 as telogen, new diiodocompounds of formula I(C3F6)m(C2F4)n(C3F6)pI n = 2,3,4 m = 0,1,2 p = 1,2 are obtained.In both cases there are high yields, based both on iodine and on olefin.