3,5-Diiodosalicylaldehyde

Base Information

• Chemical Name: 3,5-Diiodosalicylaldehyde
• CAS No.: 2631-77-8
• Molecular Formula: C7H4I2O2
• Molecular Weight: 373.917
• Hs Code.: 29130000
• European Community (EC) Number: 220-117-2
• NSC Number: 83969
• UNII: WDZ9NS6YPP
• DSSTox Substance ID: DTXSID40180931
• Nikkaji Number: J192.151G
• Wikidata: Q83051542
• ChEMBL ID: CHEMBL3660331
• Mol file: 2631-77-8.mol

Synonyms:3,5-Diiodosalicylaldehyde;2631-77-8;2-Hydroxy-3,5-diiodobenzaldehyde;Benzaldehyde, 2-hydroxy-3,5-diiodo-;WDZ9NS6YPP;3,5-Diiodo-2-hydroxybenzaldehyde;EINECS 220-117-2;MFCD00003321;NSC-83969;2-Hydroxy-3,5-diiodo-benzaldehyde;NSC83969;Benzaldehyde,2-hydroxy-3,5-diiodo-;UNII-WDZ9NS6YPP;Salicylaldehyde, 3,5-diiodo-;SCHEMBL1527177;CHEMBL3660331;15-METHYLHEPTADECANOICACID;DTXSID40180931;3,5-Diiodosalicylaldehyde, 97%;BDBM110994;AMY31562;2-Hydroxy-3,5-diiodobenzaldehyde #;BBL023212;NSC 83969;STK016290;AKOS000120864;CS-W009763;AS-62132;SY037876;D4848;FT-0614631;EN300-18189;D70906;J-016378;US8614253, .3-25;Z57313908

Chemical Property of 3,5-Diiodosalicylaldehyde

Chemical Property:

• Appearance/Colour: pale yellow powder
• Vapor Pressure: 0.000481mmHg at 25°C
• Melting Point: 109-110 °C(lit.)
• Refractive Index: 1.787
• Boiling Point: 304.6 °C at 760 mmHg
• PKA: 6.12±0.23(Predicted)
• Flash Point: 138 °C
• PSA: 37.30000
• Density: 2.602 g/cm³
• LogP: 2.41390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Air & Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 373.83007
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

97% ^*data from raw suppliers

3,5-Diiodosalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1C=O)O)I)I
• General Description: 3,5-Diiodosalicylaldehyde, also known as 3,5-diiodo-2-hydroxybenzaldehyde, is a key structural scaffold in the synthesis of iodinated hydrazide-hydrazones and related analogues, demonstrating potent antibacterial activity, particularly against Gram-positive bacteria such as methicillin-resistant *Staphylococcus aureus* (MRSA). Its incorporation into these compounds enhances antimicrobial efficacy, likely due to the electron-withdrawing effects of the iodine substituents, which contribute to improved biological activity. Additionally, derivatives featuring this moiety exhibit variable cytotoxicity, with selective toxicity toward cancer cell lines over normal human cells, suggesting its utility in the development of dual antimicrobial and anticancer agents.

Technology Process of 3,5-Diiodosalicylaldehyde

There total 14 articles about 3,5-Diiodosalicylaldehyde 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: 100.0%

1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → 2,4-dichlorophenacyl bromide (2631-72-3)

Guidance literature:

With bromine; In 1,4-dioxane; diethyl ether; for 0.5h; Ambient temperature;

Reference yield: 87.0%

salicylaldehyde (90-02-8) → 3,5-diodosalicylaldehyde (2631-77-8)

Guidance literature:

salicylaldehyde; With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃;

With sodium thiosulfate; In water; dimethyl sulfoxide;

With ammonium chloride; In water;

DOI:10.1021/jo9007892

Reference yield: 72.0%

1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → 2,2-dibromo-1-(2,4-dichlorophenyl)ethanone (24123-68-0) + 2,4-dichlorophenacyl bromide (2631-72-3)

Guidance literature:

With trimethylsilyl bromide; potassium nitrate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2011.01.039

upstream raw materials:

salicylaldehyde

2-methyl-benzyl alcohol

1-(2,4-dichlorophenyl)ethan-1-one

2,2-dibromo-1-(2,4-dichlorophenyl)ethanone

Downstream raw materials:

3,5-diiodosalicylic acid

2-hydroxy-3,5-diiodo-benzaldehyde-oxime

2,4-diiodo-6-(phenylimino-methyl)-phenol

2-hydroxy-3,5-diiodo-benzaldehyde-thiosemicarbazone

Refernces

Iodinated 1,2-diacylhydrazines, benzohydrazide-hydrazones and their analogues as dual antimicrobial and cytotoxic agents

10.1016/j.bmc.2021.116209

This research aimed to evaluate the potential of iodinated hydrazide-hydrazones and their analogues as dual antimicrobial and cytotoxic agents, addressing the increasing resistance of bacterial and fungal pathogens to existing treatments. The study synthesized and screened twenty-two iodinated hydrazide-hydrazones and ten 1,2-diacylhydrazines, along with their three reduced analogues, for their antibacterial, antifungal, and cytotoxic properties. The compounds were tested against eight bacterial and eight fungal strains, and their cytotoxicity was assessed on HepG2 and HK-2 cell lines. The study found that certain derivatives, particularly those containing the 3,5-diiodosalicylidene scaffold, exhibited potent antibacterial activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), with low minimum inhibitory concentrations (MIC) values. Some compounds also showed antifungal activity and variable degrees of cytotoxicity, with normal human cells exhibiting lower sensitivity. The research concluded that these compounds, especially those with electron-withdrawing groups like F, Cl, CF3, and NO2, have potential as antimicrobial and cytotoxic agents. The chemicals used in the process included various substituted benzohydrazides, 2-/4-hydroxy-3,5-diiodobenzaldehydes, 3,5-diiodosalicylic acid, and their derivatives, as well as reagents for biological assays and cytotoxicity tests.

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