507-63-1

Basic information

• Product Name: Perfluorooctyl iodide
• Synonyms: 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodo-octan;1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-8-iodooctane;1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodo-Octane;1-Iodoheptadecafluorooctane;1-iodoperfluorooctane98%;heptadecafluoro-1-iodo-octan;Octane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodo-;Octane, heptadecafluoro-1-iodo-
• CAS NO: 507-63-1
• Molecular Formula: C₈F₁₇I
• Molecular Weight: 545.96
• EINECS: 208-079-5
• Product Categories: Organic Fluorides;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;Alkyl;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;F-Tagged;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Thiophenes ,Thiazolines/Thiazolidines
• Mol File: 507-63-1.mol

Chemical Properties

• Melting Point: 25 °C
• Boiling Point: 160-161 °C(lit.)
• Flash Point: 160-161°C
• Appearance: Clear colorless to yellow or light pink/Liquid After Melting
• Density: 2.067 g/mL at 20 °C(lit.)
• Vapor Pressure: 3.08mmHg at 25°C
• Refractive Index: n20/D 1.329(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• Sensitive: Light Sensitive
• BRN: 1717141
• CAS DataBase Reference: Perfluorooctyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Perfluorooctyl iodide(507-63-1)
• EPA Substance Registry System: Perfluorooctyl iodide(507-63-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 2922
• WGK Germany: 3
• RTECS: RG9700050
• F: 8
• TSCA: T
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 507-63-1(Hazardous Substances Data)

Usage

Chemical Properties

clear light pink liquid after melting

Uses

Different sources of media describe the Uses of 507-63-1 differently. You can refer to the following data:
1. Perfluorooctyl Iodide is a perfluoroalkyl iodide used in organocatalysis via substrate activation by halogen bonding. Perfluorooctyl Iodide is a potential candidate substitute for banned Halon fire extinguishers.
2. Heptadecafluoro-1-iodooctane has been used as monodentate donor to investigate anion receptor complexes of mono-, bi- and tridentate donors with a variety of anions in the gas phase using both experimental and theoretical approaches.

Safety Profile

Slightly toxic by intravenous route. When heated to decomposition it emits toxic vapors of Fí and Ií.

InChI:InChI=1/C8F17I/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)26

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 354-64-3 Pentafluoroethyl iodide 
• 423-39-2 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane 
• 68555-67-9 Sodium n-perfluorooctanesulfinate 
• 1367879-47-7 C₆H₁₅N*C₈F₁₇I 
• 1367879-48-8 C₈F₁₇I*C₈H₁₈OS 
• 1367879-52-4 C₇H₁₃N*C₈F₁₇I 
• 1367879-50-2 C₈F₁₇I*C₁₂H₂₇OP 
• 307-35-7 perfluorooctyl sulfofluorure 
• 359-69-3 Tris(pentafluoraethyl)arsan 
• 7553-56-2 iodine 
• 32395-49-6 Bis(pentafluoraethyl)-fluorarsan 
• 355-43-1 n-perfluorohexyl iodide 

Downstream Products

• 335-65-9 hydroperfluorooctane 
• 307-34-6 Perfluorooctane 
• 55009-88-6 n-perfluorooctylacetylene 
• 52717-11-0 1-phenyl-2-perfluorooctyl acetylene 
• 132815-95-3 PhSeC₈F₁₉ 
• 143760-67-2 3-Heptadecafluorooctyl-2-phenylselanyl-tetrahydro-pyran 
• 355-49-7 perfluorocetane 
• 375-95-1 perfluorononanoic acid 
• 92746-93-5 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Heptadecafluoro-nonanoic acid 2-hydroxy-ethyl ester 
• 335-67-1 Perfluorooctanoic acid 
• 113999-60-3 1-phenyl-2-(perfluorooctyl)propene 
• 78960-67-5 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-1-phenylnonan-1-one 
• 133405-24-0 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10,10-dimethoxy-undecane 
• 133377-50-1 2-Heptadecafluorooctyl-1,1-dimethoxy-cyclohexane 

Relevant articles and documents

Production method of fluoroalkyl iodide

The invention discloses a production method of a fluoroalkyl iodide, and particularly discloses a production method of a fluoroalkyl iodide as shown in a formula (I) as shown in the specification. Theproduction method of the fluoroalkyl iodide as shown in the formula (I) as shown in the specification comprises the following step: in a first solvent, subjecting a compound as shown in a formula (II) as shown in the specification and an iodide to an iodination reaction as shown in the specification. The raw materials used in the method are easy to obtain, and prices are low; and the method is high in conversion rate and yield, and the tolerability to functional groups is high.

PROCESS FOR PRODUCING FLUOROALKYL IODIDE TELOMER

A novel process for producing a fluoroalkyl iodide telomer is provided, which is able to obtain a fluoroalkyl iodide telomer having a desired chain length, efficiently. A fluoroalkyl iodide represented by the general formula RfI (wherein Rf is a C1-10 fluoroalkyl group) and tetrafluoroethylene are used as a telogen and a taxogen, respectively. These compounds are supplied to a distillation apparatus. In a reaction zone located in an intermediate part of the distillation apparatus, the compounds are subjected to a telomerization reaction in the presence of a metal catalyst with heating to generate a fluoroalkyl iodide telomer represented by the general formula Rf(CF2CF2)nI (wherein Rf is the same as defined above and n is an integer of 1-4). Thereafter, a fraction comprising the fluoroalkyl iodide telomer is separated by distillation.

Thermodynamics of halogen bonding in solution: Substituent, structural, and solvent effects

A detailed study of the thermodynamics of the halogen-bonding interaction in organic solution is presented. 19F NMR titrations are used to determine association constants for the interactions of a variety of Lewis bases with fluorinated iodoalkanes and iodoarenes. Linear free energy relationships for the halogen bond donor ability of substituted iodoperfluoroarenes XC 6F4I are described, demonstrating that both substituent constants (σ) and calculated molecular electrostatic potential surfaces are useful for constructing such relationships. An electrostatic model is, however, limited in its ability to provide correlation with a more comprehensive data set in which both halogen bond donor and acceptor abilities are varied: the ability of computationally derived binding energies to accurately model such data is elucidated. Solvent effects also reveal limitations of a purely electrostatic depiction of halogen bonding and point to important differences between halogen bonding and hydrogen bonding.

Fluoroalkyl iodide and its production process

A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state is under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.

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.

Metallic copper catalyst for polyfluoroalkylethyl iodide production and process for producing polyfluoroalkylethyl iodide

The present invention provides a metallic copper catalyst for use in an ethylene addition reaction to polyfluoroalkyl iodides, a process for efficiently producing a polyfluoroalkylethyl iodide using such a metal copper catalyst in an ethylene addition reaction to a polyfluoroalkyl iodide, and a process for efficiently producing a polyfluoroalkylethyl iodide from a polyfluoroalkyl iodide using the same metallic copper catalyst in a telomerization reaction and a subsequent ethylene addition reaction.

METHOD FOR CONTINUOUS PRODUCTION OF A PERFLUOROALKYL IODIDE TELOMER

The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160°C under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.

METHOD FOR PRODUCING FLUOROALKYL IODIDE TELOMER MIXTURE AND METHOD FOR PRODUCING FLUORINE-CONTAINING (METH)ACRYLATE ESTER

A mixture of fluoroalkyl iodide telomers represented by the formula: Rf(CF2CF2)nl wherein Rf represents a fluoroalkyl group whose number of carbon atoms is in the range of 1 to 10, with the polymerization degree n equal to or more than k that is an integer of 3 or more, is obtained by reacting a fluoroalkyl iodide with tetrafluoroethylene in a first reactor followed by fractionating a first reaction mixture which contains fluoroalkyl iodide telomers of low polymerization degree, as well as by reacting the telomer with n of (k-1) separated from the first reaction mixture with tetrafluoroethylene in the second reactor.

Highly selective photochemical synthesis of perfluoroalkyl bromides and iodides

Highly fluorinated alkyl iodides are conveniently synthesized by telomerization of a fluoroalkyl-iodide, RI, with, e.g., C2F4. Normally, the reaction, often carried out in the liquid phase with a radical initiator, gives products with a broad distribution of molecular weights. In this work, we report a method that obtains selectively products of a desired molecular weight: this method is a photochemically induced reaction in the gas phase; the gas is circulated through a trap or a rectification still which continuously removes the heavier products, whereas the more volatile molecules return to the photoreactor. An analysis by rate equations shows which control parameters are important, and by a suitable choice of these parameters, we obtained a better selectivity for, e.g., C8F17I than previously. This method also works with BrC2F4Br instead of an iodide. In this case, we demonstrated in a small laboratory setup with simple low-pressure Hg lamps (5 × 30 W), a productivity of more than 0.5 kg/day. In the telomerization of CF3Br or HC2F4Br with C2F4 we found, however, a few percent of dibromide side products which are sometimes difficult to separate because of similar boiling points. For this case, it is better to synthesize the iodides instead, and then exchange the I for Br, if desired.

THERMOLYSIS AND UV-PHOTOLYSIS OF PERFLUORINATED IODO-ALKANES AND IODO-OXAALKANES: THERE IS A PREFERRED REACTION CHANNEL

The thermal stability of perfluorinated iodides depends on their structure and decreases in the order of RFCF2CF2I>RFCF2CF(CF3)I>RFOCF(CF3)I=RFCF2C(CF3)2I.The major decomposition path consists of the elimination of an unsaturated compound (CF2=CF2, CF2=CF-CF3, O=CF-CF3, CF2=C(CF3)2, respectively) with concomitant formation of RFI.The highest selectivities were found for tertiary iodides and 2-iodo-3-oxaalkanes, whose decomposition is virtually irreversible.UV-photolysis of the iodo-compounds gave the same products as the thermolysis reactions.