79865-03-5

Basic information

• Product Name: HEPTAFLUOROBENZYL IODIDE
• Synonyms: HEPTAFLUOROBENZYL IODIDE;HEPTAFLUOROBENZYL IODIDE, TECH.;HEPTAFLUOROBENZYL IODIDE 95%;Heptafluorobenzyliodide97%;1-[Difluoro(iodo)methyl]-2,3,4,5,6-pentafluorobenzene, alpha,alpha,2,3,4,5,6-Heptafluoro-alpha-iodotoluene
• CAS NO: 79865-03-5
• Molecular Formula: C₇F₇I
• Molecular Weight: 343.97
• Product Categories: Aryl;C7;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 79865-03-5.mol

Chemical Properties

• Boiling Point: 153 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 2.185 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• CAS DataBase Reference: HEPTAFLUOROBENZYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTAFLUOROBENZYL IODIDE(79865-03-5)
• EPA Substance Registry System: HEPTAFLUOROBENZYL IODIDE(79865-03-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 79865-03-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
HEPTAFLUOROBENZYL IODIDE is used as a synthetic building block for the creation of fluorine-containing compounds, leveraging its reactivity and electron-withdrawing properties to facilitate various chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, HEPTAFLUOROBENZYL IODIDE is used as a key intermediate in the synthesis of drug molecules, contributing to the development of new medications through its role in chemical reactions that form complex molecular structures.
Used in Agrochemical Industry:
HEPTAFLUOROBENZYL IODIDE is employed in the agrochemical field as a component in the synthesis of pesticides and other crop protection agents, enhancing their effectiveness and selectivity due to the unique properties of fluorinated compounds.
Used in Materials Science:
In materials science, HEPTAFLUOROBENZYL IODIDE is utilized in the preparation of advanced materials with specific properties, such as high thermal stability and chemical resistance, which are crucial for various industrial applications.

InChI:InChI=1/C7F7I/c8-2-1(7(13,14)15)3(9)5(11)6(12)4(2)10

Upstream product

• 434-64-0 perfluorotoluene 
• 35523-39-8 heptafluorobenzyl bromide 

Downstream Products

• 1373037-95-6 C₂₂H₁₇F₆NO₃ 
• 1373037-87-6 C₂₂H₁₈F₇NO₃ 
• 1180131-18-3 (S)-2-(perfluorobenzyl)octan-1-ol 
• 1349737-47-8 [(η5-pentamethylcyclopentadienyl)RhI(CF2C6F5)(PPh3)] 
• 1349737-31-0 [(η5-pentamethylcyclopentadienyl)RhI(CH2CH2CF2C6F5)(PPh3)] 
• 1217744-82-5 3-perfluorobenzylchroman-2-one 
• 1217744-74-5 2-perfluorobenzylcyclohexanone 
• 1217744-90-5 C₁₈H₁₄F₇NO 
• 1118766-33-8 Ir(CO)2(2,4-pentanedionato)(CF₂C₆F₅)(I) 
• 184682-63-1 (η(5)-pentamethylcyclopentadienyl)iodo(perfluorobenzyl)carbonylcobalt(III) 

Relevant articles and documents

A novel double insertion of the difluoromethylene unit from trifluoromethylcopper into the carbon-copper bond of perfluoroaryl- and perfluorovinylcopper reagents: Preparation, mechanism and applications of new fluorinated copper reagents

Reaction of CF3Cu with pentafluorophenylcopper, prepared from CuBr and pentafluorophenylcadmium C6F5CdX, gave the double CF2 unit insertion product, C6F5CF2CF2Cu, in 70-80% yields. The insertion reaction also worked well with CF3MX (M=Cd, Zn; X=Br, CF3) and C6F5CdX in the presence of CuBr at room temperature to afford C6F5CF2CF2Cu. With a vinylcopper analog, (Z)-CF3CFCFCu, double CF2 insertion also occurred resulting in the formation of (E)-CF3CFCFCF2CF2Cu, which could be trapped with allyl bromide to give (E)-CF3CFCFCF2CF2CH2CHCH 2. When CF2CFCu was used as a substrate, (E)-CF3CFCFCF2CF2Cu was observed, but in low yield. A mechanism for this novel double CF2 insertion is proposed to involve a copper difluorocarbenoid complex intermediate, which inserted into the carbon-copper bond of the fluorinated phenyl and vinyl coppers to form fluorinated benzyl or allyl copper reagents. The intermediate benzyl or allyl coppers are more reactive than the pentafluorophenyl or vinylcoppers and rapidly undergo insertion of another CF2 unit. Perfluorobenzylcopper was prepared independently and gave C6F5CF2CF2Cu on reaction with CF3Cu. The resultant new copper reagent, such as C6F5CF2CF2Cu, showed good thermal stability and reactivity. Halogenation of the copper reagent gave the corresponding halides C6F5CF2CF2X, and insertion of sulfur dioxide into the carbon-copper bond followed by trapping with allyl halide gave the corresponding allylic sulfones. C6F5CF2CF2Cu also participated in coupling reactions with allyl halides, vinyl halides and aryl halides to give the coupled products in good yields. Selective functionalization of both aryl rings of the fluorinated diarylethanes with a variety of reagents has also been demonstrated.

A new route to polyfluorinated trifluoromethanesulfonates. Synthesis of perfluoroallyl and perfluorobenzyl triflates

Polyfluoroalkyl trifluoromethanesulfonates (triflates) can be prepared in good to excellent yields by the reaction of halofluoroalkanes such as CFC-11, CFC-113 and CFC-112 with boron triflate at 20-25 deg C.Hexafluoropropene (HFP) is more active and react

The preparation, stability and reactivity of perfluorobenzyl-cadmium and -copper reagents

Perfluorobenzyl bromide reacts readily with acid-washed cadmium powder in DMF at room temperature to give the F-benzylcadmium reagent.Metathesis of the F-benzylcadmium reagent with Cu(I)Br at -40 deg C to -35 deg C in DMF affords the F-benzylcopper reagen