608-74-2

Usage

Uses

Used in Organic Synthesis:
Periodobenzene is used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. Its reactivity and versatility make it a valuable component in the creation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, periodobenzene is used as a starting material for the production of various drugs. Its properties allow for the development of new medicinal compounds with potential therapeutic applications.
Used in Organic Chemistry Research:
As a reagent in organic chemistry, periodobenzene is employed in research for its role in facilitating carbon-carbon bond formation. This makes it instrumental in advancing the understanding of organic reactions and the development of new synthetic methods.
Used in Chemical Analysis:
Periodobenzene can also be utilized in chemical analysis for the identification and characterization of compounds due to its unique chemical properties and reactivity.

InChI:InChI=1/C6I6/c7-1-2(8)4(10)6(12)5(11)3(1)9

Upstream product

• 121-91-5 isophthalic acid 
• 100-21-0 terephthalic acid 
• 65-85-0 benzoic acid 
• 71-43-2 benzene 
• 515-42-4 sodium phenylsulfonate 
• 100-56-1 phenylmercury(II) chloride 
• 98-95-3 nitrobenzene 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 
• 591-50-4 iodobenzene 
• 624-38-4 para-diiodobenzene 

Downstream Products

• 87-85-4 Hexamethylbenzene 
• 89567-89-5 hexakis(trifluoromethylthio)benzene 
• 354-32-5 trifluoracetyl chloride 
• 115162-16-8 C₆I₆⁽²⁺⁾*2CF₃O₃S^(1-) 
• 115162-13-5 C₆ClI₅⁽¹⁺⁾*2CF₃O₃S^(1-) 
• 89567-90-8 hexakis(pentafluorophenylthio)benzene 
• 103410-36-2 C₄₂F₃₀Se₆ 
• 89567-91-9 Hexakisbenzene 
• 23746-55-6 (E)-3-[4-(2-methoxycarbonylvinyl)phenyl]acrylic acid methyl ester 
• 123568-26-3 (E)-3-[2,5-Bis-((E)-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester 
• 123568-25-2 (E)-3-[2,4,5-Tris-((E)-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester 
• 110846-75-8 Hexakis(phenylethynyl)benzene 
• 113705-23-0 pentakis((trimethylsilyl)ethynyl)benzene 
• 100516-62-9 1,2,3,4,5,6-hexa(2-trimethylsilylethynyl)benzene 

Relevant academic research and scientific papers

Halogenated benzene cation radicals

The halogenated benzenes C6HF5, 2,4,6-C 6H3F3, 2,3,5,6-C6H2F 4, C6F6, C6Cl6, C 6Br6, and C6I6 were converted into their corresponding cation radicals by using various strong oxidants. The cation-radical salts were isolated and characterized by electron paramagnetic resonance (EPR) spectroscopy and by single-crystal X-ray diffraction. The thermal stability of the cation radicals increased with decreasing hydrogen content. As expected, the cation radicals [C6HF5] + and 2,3,5,6-[C6H2F4]+ had structures with the same geometry as C6HF5 and 2,3,5,6-[C6H2F4]. In contrast, the cation radicals [C6F6]+, [C6Cl 6]+, and possibly also [C6Br6] + exhibited Jahn-Teller-distorted geometries in the crystalline state. In the case of C6F6+Sb2F 11-, two low-symmetry geometries were observed in the same crystal. Interestingly, the structures of the cation radicals 2,4,6-[C 6H3F3]+ and C6I 6+ did not exhibit Jahn-Teller distortions. DFT calculations showed that the explanation for the lack of distortion of these cations from the D3h or D6h symmetry of the neutral benzene precursor was different for 2,4,6-[C6H3F 3]+ than for [C6I6]+. Copyright

A direct and convenient synthesis of periodoarenes using molecular iodine

Molecular iodine exhaustively iodinates aromatic hydrocarbons in the presence of potassium peroxodisulfate, concentrated sulfuric acid, and trifluoroacetic acid to give the periodinated aromatic compounds. Benzene and other moderately activated and deactivated arenes are readily converted into the corresponding periodinated derivatives in good to high yields.

Polyiodination on benzene at room temperature. A regioselective synthesis of derivatives

Reaction of IPy2BF4 with benzene and CF3SO3H in CH2Cl2 gives regioselectively polyiodinated compounds at room temperature, providing a definitely easy synthetic entry to those rarely accessible benzene derivatives.

Direct Polyiodination of Benzenesulfonic Acid

Direct aromatic polyiodination of benzenesulfonic acid (using I2 and H5IO6 in H2SO4 at room temperature) was performed to test the possible intermediacy of C6H5SO3H in the corresponding direct polyiodination of benzene to C6H2I4.The major product from C6H5SO3H was 3,4,5-triiodobenzenesulfonic acid (4).In contrast, no 4 was formed in the C6H6 reaction, showing that no significant sulfonation of C6H6 to C6H5SO3H occurred during benzene iodination.Compound 4 itself was shown to be inert under the reaction conditions.A pathway is proposed from C6H5SO3H to the other reaction products (C6I6, C6I5H, two C6I4H2 isomers, and 3,4,5-triiodophenol), which therefore avoids the intermediacy of 4.

Direct Aromatic Periodination

Periodic acid and iodine in concentrated sulfuric acid exhaustively iodinated unactivated aromatic substrates.Thus benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene were all converted to their periodo derivatives.Benzonitrile was converted to pentaiodobenzamide.This direct method compared favorably with the only general periodination procedure available, a mercuration/iododemercuration sequence.Partially iodinated products were obtained under less vigorous conditions.Thus, triiodo derivatives were obtained from nitrobenzene, benzo-ic acid, and toluene; tetraiodo derivatives were obtained from benzene, chlorobenzene, and trifluorobenzene.