Diphenyleneiodonium chloride

Base Information

• Chemical Name: Diphenyleneiodonium chloride
• CAS No.: 4673-26-1
• Molecular Formula: C12H8I.Cl
• Molecular Weight: 314.553
• Hs Code.: 2903999090
• European Community (EC) Number: 805-298-3
• UNII: 7M9D81YZ2N
• DSSTox Substance ID: DTXSID00196932
• Wikidata: Q4162480
• Pharos Ligand ID: SDHXRYMFUGTN
• ChEMBL ID: CHEMBL397686
• Mol file: 4673-26-1.mol

Synonyms:diphenylene iodonium;diphenyleneiodium chloride;diphenyleneiodonium;diphenyleneiodonium chloride;diphenyleneiodonium sulfate (2:1);diphenyleneiodonium sulfate (2:1), 125I-labeled;diphenyleneiodonium, 131I-labeled

Chemical Property of Diphenyleneiodonium chloride

Chemical Property:

• Melting Point: 312-322oC
• PSA: 0.00000
• LogP: -3.20060
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 5 mg/ml with warming)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 313.93593
• Heavy Atom Count: 14
• Complexity: 170

Purity/Quality:

≥97% ^*data from raw suppliers

Diphenyleneiodonium Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3[I+]2.[Cl-]
• Recent ClinicalTrials: Efficacy of Fixed Combination of Beclomethasone Dipropionate (BDP) + Formoterol Fumarate (FF) + Glycopyrronium Bromide (GB) (CHF 5993)Administered Via Dry Powder Inhaler (DPI) in Chronic Obstructive Pulmonary Disease (COPD)
• Description: Diphenyleneiodonium (DPI) is an inhibitor of NADPH oxidase (NOX; EC50 = 0.1 μM in HeLa cells). It also inhibits nitric oxide synthase (NOS; IC50 = 0.05 μM in isolated mouse peritoneal macrophages). DPI (10, 50, and 100 μM) induces the production of reactive oxygen species (ROS) in, and apoptosis of, human umbilical vein endothelial cells (HUVECs). It inhibits NETosis induced by phorbol 12-myristate 13-acetate (PMA; ) in isolated human neutrophils when used at a concentration of 10 μM. DPI (2 mg/kg) reduces tumor growth in HT-29 and LS 174T colon cancer mouse xenograft models.
• Uses: Binds strongly to flavoproteins and thus inhibits NO synthase, NADG reductase and NADPH oxidase. Solubility: 5 mg in 1.7 mL of H2O:DMSO 40:60; 10 mg in 1.1 mL H2O:DMSO 10:90 Diphenyleneiodonium Chloride binds strongly to flavoproteins and thus inhibits NO synthase, NADG reductase and NADPH oxidase. Diphenyleneiodonium Chloride solubility: 5 mg in 1.7 mL of H2O:DMSO 40:60; 10 mg in 1.1 mL H2O:DMSO 10:90 Diphenyleneiodonium Chloride binds strongly to flavoproteins and thus inhibits NO synthase, NADG reductase and NADPH oxidase.Diphenyleneiodonium Chloride solubility: 5 mg in 1.7 mL of H2O:DMSO 40:60; 10 mg in 1.1 mL H2O:DMSO 10:90

Technology Process of Diphenyleneiodonium chloride

There total 1 articles about Diphenyleneiodonium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Dibenzoiodolyl pyrrolidinedithiocarbamate → 2-iodobiphenyl (2113-51-1) + bis-(pyrrolidine-1-thiocarbonyl)-disulfane (496-08-2) + diphenyleneiodonium chloride (4673-26-1)

Guidance literature:

In chloroform; for 144h; Ambient temperature;

Reference yield:

diphenyleneiodonium chloride (4673-26-1) → 2-Iod-2'-biphenylylphenyliodoniumiodid

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: I₂ / tetrahydrofuran

With iodine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00825a011

Reference yield:

diphenyleneiodonium chloride (4673-26-1) → 2-Biphenylylphenyliodoniumfluoroborat

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: HBF₄ / tetrahydrofuran

With tetrafluoroboric acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00825a011

Downstream raw materials:

5-(4-chloro-phenyl)-5H-5λ³-dibenzoiodole

5-phenyl-5H-5λ³-dibenzoiodole

5-p-tolyl-5H-5λ³-dibenzoiodole

2'-chloro-[1,1'-biphenyl]-2-carboxylic acid

Refernces