608-74-2

Basic information

• Product Name: periodobenzene
• Synonyms: periodobenzene;1,2,3,4,5,6-hexaiodobenzene
• CAS NO: 608-74-2
• Molecular Formula: C₆I₆
• Molecular Weight: 833.49102
• EINECS: 210-169-4
• Mol File: 608-74-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 350 °C
• Boiling Point: 530.7°C at 760 mmHg
• Flash Point: 291.3°C
• Appearance: /
• Density: 3.756g/cm³
• Vapor Pressure: 8.19E-11mmHg at 25°C
• Refractive Index: 1.905
• CAS DataBase Reference: periodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: periodobenzene(608-74-2)
• EPA Substance Registry System: periodobenzene(608-74-2)

Safety Data

• Hazardous Substances Data: 608-74-2(Hazardous Substances Data)

Usage

General Description

Periodobenzene, also known as iodobenzene, is a chemical compound with the molecular formula C6H5I. It is an organoiodine compound and is one of the isomers of iodobenzene. Periodobenzene is a colorless liquid with a faint odor and is insoluble in water but soluble in organic solvents. It is commonly used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. Periodobenzene is also used as a reagent in organic chemistry, particularly in reactions involving carbon-carbon bond formation. Its reactivity and versatility make it a valuable tool in the field of organic synthesis. However, it is important to handle periodobenzene with caution as it is toxic and can cause skin and eye irritation.

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

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 articles and documents

The Periodination Reaction: Fast One-Step Synthesis of C6I6 from C6H6

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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.

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.