375-80-4

Basic information

• Product Name: 1,6-Diiodododecafluorohexane
• Synonyms: Hexane,1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodo-;PERFLUORO-1,6-DIIODOHEXANE;1,6-DIIODODODECAFLUOROHEXANE;1,6-DIIODOPERFLUOROHEXANE;1,4-DIIODOOCTAFLUOROHEXANE;DODECAFLUORO-1,6-DIIODOHEXANE;1,6-Diiodododecafluorohexane~Dodecafluoro-1,6-diiodohexane;Dodecafluoro-1,6-diodohexane
• CAS NO: 375-80-4
• Molecular Formula: C₆F₁₂I₂
• Molecular Weight: 553.85
• EINECS: 206-794-7
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 375-80-4.mol

Chemical Properties

• Melting Point: 25-30 °C(lit.)
• Boiling Point: 173-174 °C(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 2,357 g/cm3
• Vapor Pressure: 1.333-1013.25hPa at 25-180℃
• Refractive Index: 1.398
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Sensitive: Light Sensitive
• BRN: 1822186
• CAS DataBase Reference: 1,6-Diiodododecafluorohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Diiodododecafluorohexane(375-80-4)
• EPA Substance Registry System: 1,6-Diiodododecafluorohexane(375-80-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 375-80-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,6-Diiodododecafluorohexane is used as a key intermediate in the synthesis and characterization of fluorinated telomers containing vinylidene fluoride and hexafluoropropene. Its unique structure and properties make it an essential component in the production of these specialized materials.
Used in Polymer Industry:
In the polymer industry, 1,6-Diiodododecafluorohexane is used as a monomer for the production of fluoropolymers. These polymers are known for their exceptional chemical resistance, thermal stability, and non-stick properties, making them ideal for applications such as coatings, lubricants, and electrical insulation.
Used in Pharmaceutical Industry:
1,6-Diiodododecafluorohexane is also used in the pharmaceutical industry as a component in the development of new drugs. Its unique chemical properties allow it to be used in the synthesis of various drug candidates, particularly those targeting specific biological pathways or receptors.
Used in Electronics Industry:
In the electronics industry, 1,6-Diiodododecafluorohexane is used as a material in the fabrication of certain electronic components due to its excellent dielectric properties and chemical stability. This makes it suitable for applications such as insulating materials in capacitors and other electronic devices.
Used in Environmental Applications:
1,6-Diiodododecafluorohexane is also utilized in environmental applications, such as in the development of new materials for water treatment and air purification. Its chemical properties make it an effective component in the creation of advanced filtration systems and other environmental technologies.

InChI:InChI=1/C6F12I2/c7-1(8,3(11,12)5(15,16)19)2(9,10)4(13,14)6(17,18)20

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 375-50-8 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane 
• 354-65-4 1,2-diiodotetrafluoroethane 
• 678-45-5 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid 
• 89740-34-1 sodium 6-chloro-1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexanesulfinate 
• 16486-97-8 1-Chloro-1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-6-iodo-hexane 
• 918-22-9 1,6-dibromo-1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexane 
• 422-91-3 1,1,2,2,3,3-hexafluoro-1,3-diiodopropane 
• 75-38-7 Vinylidene fluoride 
• 1967-93-7 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioyl dichloride 

Downstream Products

• 336-08-3 perfluoroadipic acid 
• 1424373-26-1 1,6-bis(diphenylthiophosphinyl)perfluorohexane 
• 1208999-65-8 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodooctadecyl benzoate 
• 1208999-63-6 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodotetradecyl benzoate 

Relevant articles and documents

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)

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.

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

Solvent effects on the reaction of perfluoroalkyl iododes and α,ω-perfluoroalkyl diiodides with cadmium powder and dimethylcadmium

Reaction of RfI (Rf=C6F13 or C8F17) with Cd powder in DMF at room temperature under N2 afforded RfCdX (X=I or Rf) in moderate (48-52percent) yield.Although no reaction was observed with Cd powder and RfI (Rf=C6F13 or C8F17) in CH3CN at room temperature, reaction at reflux gave the homocoupled products C6F13-C6F13 (67percent) and C8F17-C8F17 (61percent) respectively.No F-alkylcadmium reagent was detected by 19F NMR spectroscopy.Similarly, the reaction of I(CF2)nI (n=3, 4) with Cd powder in DMF and CH3CN was examined.In DMF at room temperature, the new dicadmium reagents ICd(CF2)nCdI and ICd(CF2)2nCdI (60-65percent combined yield) were formed.No reaction was observed with Cd powder and I(CF2)nI (n=3, 4, 6) in CH3CN at room temperature, but at reflux a mixture of higher α,ω-diiodoperfluoroalkanes, i.e.I(CF2)2nI, I(CF2)3nI, I(CF2)4nI, I(CF2)5nI, resulted.Treatment of I(CF2)nI (n=3, 4) with CdMe2 (1:2) in CH3CN afforded the new ω-iodo F-alkylcadmium reagents, 2Cd*(CH3CN), in 96percent (n=3) and 57percent (n=4) yields.Reaction of Me2Cd with either ICF2CF2I or BrCF2CF2I in CH3CN or HMPA at 0 deg C resulted in tetrafluoroethylene only.

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.

A Convenient One-Stage Synthesis of Some Diiodoperfluoroalkanes By Using Tetrafluoroethylene Derived From Poly(tetrafluoroethylene) Waste

Tetrafluoroethylene was prepared by a thermal depolymerization of poly(tetrafluoroethylene) waste.The gaseous mixture containing 95-97percent tetrafluoroethylene has been used without further purification in a direct reaction with iodine to synthesize some α,ο-diidoperfluoroalkenes at temperature 285+/-5 deg C for 8 h.Stoichiometric one to one ratio of the reagents has been found to produce higher diidoperfluoroalkenes yield per unit reaction volume than synthesis in the presence of an excess of tetrafluoroethylene.This approach provides a rapid one-pot procedure to these valuable reagents without any dangerous step.