73178-08-2

Basic information

• Product Name: 1-[hydroxy(tosyloxy)iodo]-4-bromobenzene
• Synonyms: 1-[hydroxy(tosyloxy)iodo]-4-bromobenzene
• CAS NO: 73178-08-2
• Molecular Weight: 471.11
• Mol File: 73178-08-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-[hydroxy(tosyloxy)iodo]-4-bromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[hydroxy(tosyloxy)iodo]-4-bromobenzene(73178-08-2)
• EPA Substance Registry System: 1-[hydroxy(tosyloxy)iodo]-4-bromobenzene(73178-08-2)

Safety Data

• Hazardous Substances Data: 73178-08-2(Hazardous Substances Data)

Upstream product

• 41018-52-4 (4-bromophenyl)-λ³-iodanediyl diacetate 
• 104-15-4 toluene-4-sulfonic acid 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 1382355-28-3 (2-(2-(3,3-diethylureido)ethyl)phenyl)(4-bromophenyl)iodonium p-toluenesulfonate 
• 1382355-18-1 (2-(2-acetamidoethyl)phenyl)(4-bromophenyl)iodonium p-toluenesulfonate 
• 1382355-08-9 (2-(2-(benzyloxycarbonylamino)ethyl)phenyl)(4-bromophenyl)iodonium p-toluenesulfonate 
• 1382354-98-4 (2-(2-(t-butoxycarbonylamino)ethyl)phenyl)(4-bromophenyl)iodonium p-toluenesulfonate 
• 85925-30-0 Toluene-4-sulfonate(4-bromo-phenyl)-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-47-9 Toluene-4-sulfonate(4-bromo-phenyl)-(5-methyl-furan-2-yl)-iodonium; 
• 85925-61-7 Toluene-4-sulfonate(4-bromo-phenyl)-furan-2-yl-iodonium; 
• 91228-74-9 (p-bromophenyl)(5-methyl-2-thienyl)iodonium tosylate 

Relevant articles and documents

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt-Derived Amphiphiles

Two sets of 19 amphiphiles derived from diaryliodonium salt in the form of 4-methylbenzenesulfonate salts and trifluoromethanesulfonate salts were synthesized in good yields through the oxidation of 17 different aryl iodides using oxone (potassium peroxymonosulfate) as the oxidation agent in Route I and meta-chloroperoxybenzoic acid as the oxidation agent in Routes II and III, followed by Friedel–Crafts reaction with (2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene to obtain the target compounds (1–19). Their structures were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry studies. Their surface activities were evaluated on the basis of surface tension and critical micelle concentration measurements by the Wilhelmy plate method at 25 °C. With their good water solubility, diaryliodonium salts (1–19) have excellent short-term bactericidal efficacy against Bacillus cereus in the concentration of 600 ppm at 20 °C. After compounding 1 or 18 with the broad-spectrum but skin-irritating antibacterial agent Kathon CG (methylchloroisothiazolinone in combination with methylisothiazolinone) in the ratio of 1:1 by mass, both formulations maintained lethality rate of >90% after 48 h.

Synthesis of Koser's reagent and derivatives

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Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides

The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.