Page last updated: 2024-12-05

diphenyliodonium

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Diphenyliodonium (Ph2I+) is a versatile reagent used in various organic reactions, primarily as a source of the phenyl cation. It is a white solid, typically prepared by reacting iodobenzene with mercury(II) acetate, followed by treatment with hydrochloric acid. Diphenyliodonium salts are known for their ability to initiate polymerization reactions, acting as a photoinitiator under UV irradiation. They are also used in various electrophilic aromatic substitution reactions. The phenyl cation generated from diphenyliodonium can react with various nucleophiles, including aromatic compounds, leading to the formation of new carbon-carbon bonds. Diphenyliodonium compounds are studied extensively due to their diverse applications in organic synthesis, materials science, and photochemistry. They are valuable tools for the development of new materials and pharmaceuticals.'

diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID12877
CHEMBL ID481680
CHEMBL ID1186881
SCHEMBL ID36560
MeSH IDM0098423

Synonyms (19)

Synonym
AKOS005430407
diphenyliodonium
iodoniumdiphenyl
iodonium biphenyl
iodonium, diphenyl-
NCIOPEN2_009656 ,
10182-84-0
STK325714
bdbm50256529
diphenyliodanium
CHEMBL481680 ,
di(phenyl)iodanium chloride
ozlbdymwfahsoq-uhfffaoysa-
inchi=1/c12h10i/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10h/q+1
CHEMBL1186881
FT-0624626
SCHEMBL36560
DTXSID60144196
D90020

Research Excerpts

Overview

The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process. The subsequent facile electrophilic iodination with C4 F9 I was also found to be crucial to ensure the efficient fluorination.

ExcerptReferenceRelevance
"The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process using CsF as a fluorine source, and a subsequent facile electrophilic iodination with C4 F9 I was also found to be crucial to ensure the efficient fluorination."( Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes.
Hu, J; Li, G; Zeng, Y, 2015
)
2.34

Effects

ExcerptReferenceRelevance
"Diphenyliodonium has been shown to be an irreversible, time-dependent inhibitor of NADPH cytochrome P450 oxidoreductase (EC 1.6.2.4) with the Ki for diphenyliodonium chloride being 2.8 mM. "( Inhibition of cytochrome P450 reductase by the diphenyliodonium cation. Kinetic analysis and covalent modifications.
Tew, DG, 1993
)
1.99

Toxicity

ExcerptReferenceRelevance
"The public interest steadily increases in the biological adverse effects caused by components released from resin-based dental restorations."( Cytotoxicity and induction of DNA double-strand breaks by components leached from dental composites in primary human gingival fibroblasts.
Carell, T; Durner, J; Eldenez, A; Geurtsen, W; Hickel, R; Kaina, B; Reichl, FX; Rothmund, L; Scherthan, H; Shehata, M; Styllou, P; Van Landuyt, K, 2013
)
0.39

Bioavailability

ExcerptReferenceRelevance
" Enhanced oxidative stress in hypertension and diabetes is linked to decreased nitric oxide (NO) bioavailability because of its interaction with vascular superoxide (O(2)(*-)), derived predominantly from NAD(P)H-dependent oxidases."( Increased superoxide production in hypertensive patients with diabetes mellitus: role of nitric oxide synthase.
Devine, A; Dixon, LJ; Henry, W; Hughes, SM; Johnston, GD; Leahey, W; Madden, A; McVeigh, GE; Rooney, K, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (159)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (3.14)18.7374
1990's52 (32.70)18.2507
2000's53 (33.33)29.6817
2010's46 (28.93)24.3611
2020's3 (1.89)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.80

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.80 (24.57)
Research Supply Index5.09 (2.92)
Research Growth Index5.55 (4.65)
Search Engine Demand Index47.89 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other162 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]