32024-15-0

Basic information

• Product Name: 3-Iodo-4,5-dimethoxybenzaldehyde
• Synonyms: 4,5-DIMETHOXY-3-IODOBENZALDEHYDE;3-IODO-4,5-DIMETHOXYBENZALDEHYDE;AKOS B005529;ASISCHEM R24517;3-Iodo-4,5-dimethoxybenzaldehyde~5-Iodoveratraldehyde;5-iodoveratraldehyde;Benzaldehyde, 3-iodo-4,5-dimethoxy-
• CAS NO: 32024-15-0
• Molecular Formula: C₉H₉IO₃
• Molecular Weight: 292.07
• EINECS: -0
• Product Categories: Aldehydes;C9;Carbonyl Compounds
• Mol File: 32024-15-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 63-65°C
• Boiling Point: 362.727 °C at 760 mmHg
• Flash Point: 173.171 °C
• Appearance: /
• Density: 1.706 g/cm³
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive: Air & Light Sensitive
• BRN: 1961757
• CAS DataBase Reference: 3-Iodo-4,5-dimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-4,5-dimethoxybenzaldehyde(32024-15-0)
• EPA Substance Registry System: 3-Iodo-4,5-dimethoxybenzaldehyde(32024-15-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 32024-15-0(Hazardous Substances Data)

Usage

Uses

3-Iodo-4,5-dimethoxybenzaldehyde was used in the preparation of 3-iodo-4,4′,5-trimethoxy-3′-O-tert-butyldiphenylsilyl-Z-stilbene and 3-iodo-4,4′,5-trimethoxy-3′-O-tert-butyldiphenylsilyl-E-stilbene. It may be used for the synthesis of chloropeptin I and chloropeptin II.

General Description

3-Iodo-4,5-dimethoxybenzaldehyde is an aryl iodide having an aldehyde group. It can be synthesized starting from 3,4-dihydroxy-5-iodobenzaldehyde.

InChI:InChI=1/C9H9IO3/c1-12-8-4-6(5-11)3-7(10)9(8)13-2/h3-5H,1-2H3

Upstream product

• 5438-36-8 5-iodovaniline 
• 89942-36-9 2-iodo-4-hydroxy-3-methoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 54246-07-0 3-hydroxy-5-iodo-4-methoxybenzaldehyde 
• 54246-05-8 3-iodo-4,5-dihydroxybenzaldehyde 
• 121-33-5 vanillin 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 5468-22-4 3-iodo-4,5-dimethoxybenzoic acid 
• 334969-43-6 (E)-3,4-Dimethoxy-5-iodostyryl-4-methoxybenzylsulfone 
• 692779-46-7 6-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-hex-5-ynoic acid benzyl ester 
• 692779-51-4 4-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-benzoic acid ethyl ester 

Relevant articles and documents

Targeting telomerase with radiolabeled inhibitors

The expression of telomerase in approximately 85% of cancers and its absence in the majority of normal cells makes it an attractive target for cancer therapy. However the lag period between initiation of telomerase inhibition and growth arrest makes direct inhibition alone an insufficient method of treatment. However, telomerase inhibition has been shown to enhance cancer cell radiosensitivity. To investigate the strategy of simultaneously inhibiting telomerase while delivering targeted radionuclide therapy to cancer cells,123I-radiolabeled inhibitors of telomerase were synthesized and their effects on cancer cell survival studied. An123I-labeled analogue of the telomerase inhibitor MST-312 inhibited telomerase with an IC50of 1.58?μM (MST-312 IC50: 0.23?μM). Clonogenic assays showed a dose dependant effect of123I-MST-312 on cell survival in a telomerase positive cell line, MDA-MB-435.

Halogenated trimethoprim derivatives as multidrug-resistant Staphylococcus aureus therapeutics

Incorporation of halogen atoms to drug molecule has been shown to improve its properties such as enhanced in membrane permeability and increased hydrophobic interactions to its target. To investigate the effect of halogen substitutions on the antibacterial activity of trimethoprim (TMP), we synthesized a series of halogen substituted TMP and tested for their antibacterial activities against global predominant methicillin resistant Staphylococcus aureus (MRSA) strains. Structure-activity relationship analysis suggested a trend in potency that correlated with the ability of the halogen atom to facilitate in hydrophobic interaction to saDHFR. The most potent derivative, iodinated trimethoprim (TMP-I), inhibited pathogenic bacterial growth with MIC as low as 1.25 μg/mL while the clinically used TMP derivative, diaveridine, showed resistance. Similar to TMP, synergistic studies indicated that TMP-I functioned synergistically with sulfamethoxazole. The simplicity in the synthesis from an inexpensive starting material, vanillin, highlighted the potential of TMP-I as antibacterial agent for MRSA infections.

HIGHLY 6-SUBSTITUTED -2,4-DIAMINOPYRIMIDINES AS INHIBITORS OF ANTHRAX

2,4-diaminopyrimidine compounds of generic Formula 1, where R and R' may be the same or different and are independently selected from: C1-C6 alkyl or alkenyl groups with 1, 2, 3, 4, 5 or 6 carbon atoms, which may be: branched or unbranched; saturated or unsaturated; and may or may not be substituted, are used to treat anthrax.