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Diphenyliodonium chloride (CAS 1483-72-3)

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Alternate Names:
DPI; NSC 134275
Application:
Diphenyliodonium chloride is a reagent used for electrophilic phenylation, e.g. of malonates and dithiocarboxylates
CAS Number:
1483-72-3
Purity:
≥98%
Molecular Weight:
316.57
Molecular Formula:
C12H10I•Cl
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Diphenyliodonium chloride plays a role in the realm of organic synthesis, facilitating various chemical reactions including copper-catalyzed cross-coupling of purines, the creation of acetylenic arylselenides, and the production of aryl alkynes through Sonogashira coupling. Additionally, it is pivotal in C-H functionalization processes that lead to the formation of (arylmethylene)oxindoles and the arylation of anilines. Its utility extends further into the investigation of visible-light photosensitive systems and the photolytic behavior of photoacid generators, showcasing its significance in advancing scientific understanding in organic chemistry and related fields. This compound, known for containing halogen, underscores its versatility and indispensability in crafting diverse organic entities and contributing to the broader spectrum of chemical research.


Diphenyliodonium chloride (CAS 1483-72-3) References

  1. Influence of 1-[(E)-2-(2-methyl-4-nitrophenyl)diaz-1-enyl]pyrrolidine-2-carboxylic acid and diphenyliodonium chloride on ruminal protein metabolism and ruminal microorganisms.  |  Floret, F., et al. 1999. Appl Environ Microbiol. 65: 3258-60. PMID: 10388733
  2. Reaction of reduced flavins and flavoproteins with diphenyliodonium chloride.  |  Chakraborty, S. and Massey, V. 2002. J Biol Chem. 277: 41507-16. PMID: 12186866
  3. Biological reactive intermediates that mediate dacarbazine cytotoxicity.  |  Pourahmad, J., et al. 2009. Cancer Chemother Pharmacol. 65: 89-96. PMID: 19399501
  4. Effects of thymol and diphenyliodonium chloride against Campylobacter spp. during pure and mixed culture in vitro.  |  Anderson, RC., et al. 2009. J Appl Microbiol. 107: 1258-68. PMID: 19486394
  5. Effect of thymol or diphenyliodonium chloride on performance, gut fermentation characteristics, and campylobacter colonization in growing swine.  |  Anderson, RC., et al. 2012. J Food Prot. 75: 758-61. PMID: 22488067
  6. Bonding orthodontics brackets to enamel using experimental composites with an iodonium salt.  |  Costa, AR., et al. 2014. Eur J Orthod. 36: 297-302. PMID: 24062381
  7. Dynamic Titania Nanotube Surface Achieves UV-Triggered Charge Reversal and Enhances Cell Differentiation.  |  Bai, J., et al. 2019. ACS Appl Mater Interfaces. 11: 36939-36948. PMID: 31513367
  8. Light-cured hyaluronic acid composite hydrogels using riboflavin as a photoinitiator for bone regeneration applications.  |  Abdul-Monem, MM., et al. 2021. J Taibah Univ Med Sci. 16: 529-539. PMID: 34408610
  9. Flavylium-Based Hypoxia-Responsive Probe for Cancer Cell Imaging.  |  Pewklang, T., et al. 2021. Molecules. 26: PMID: 34443527
  10. Development of the P-Arylation of Dithieno[3,2-b:2',3'-d]phosphole with Aryl Iodonium Salts.  |  Hussein, A., et al. 2023. Chempluschem. e202300133. PMID: 37084062
  11. Combined effects of diphenyliodonium chloride, pine oils, and mustard oil soaps on certain microorganisms.  |  Ahmed, Z., et al. 1969. Appl Microbiol. 17: 857-60. PMID: 4389659
  12. Aspects of the antibacterial action of diphenyliodonium chloride.  |  Gerami-Nejad, M. and Stretton, RJ. 1981. Microbios. 30: 97-107. PMID: 6457963
  13. Inhibition of cytochrome P450 reductase by the diphenyliodonium cation. Kinetic analysis and covalent modifications.  |  Tew, DG. 1993. Biochemistry. 32: 10209-15. PMID: 8399148
  14. Electrophoresis gel media: the state of the art.  |  Righetti, PG. and Gelfi, C. 1997. J Chromatogr B Biomed Sci Appl. 699: 63-75. PMID: 9392368

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Diphenyliodonium chloride, 5 g

sc-252752
5 g
$117.00