20357-24-8

Basic information

• Product Name: 5-Methoxy-2-nitrobenzaldehyde
• Synonyms: 5-METHOXY-2-NITROBENZALDEHYDE;2-NITRO-5-METHOXYBENZALDEHYDE;2-Formyl-4-methoxynitrobenzene, 3-Formyl-4-nitroanisole;Benzaldehyde, 5-methoxy-2-nitro-;m-Anisaldehyde, 6-nitro-
• CAS NO: 20357-24-8
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• Mol File: 20357-24-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 354.7 °C at 760 mmHg
• Flash Point: 184.2 °C
• Appearance: /
• Density: 1.322 g/cm³
• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-Methoxy-2-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-nitrobenzaldehyde(20357-24-8)
• EPA Substance Registry System: 5-Methoxy-2-nitrobenzaldehyde(20357-24-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 20357-24-8(Hazardous Substances Data)

Usage

Description

5-Methoxy-2-nitrobenzaldehyde is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. It is characterized by its aromatic structure, which includes a methoxy group at the 5th position and a nitro group at the 2nd position of the benzene ring. 5-Methoxy-2-nitrobenzaldehyde is known for its reactivity and versatility in chemical reactions, making it a valuable building block in the development of new molecules with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-Methoxy-2-nitrobenzaldehyde is used as a starting material for the synthesis of a novel class of cis-locked combretastatins, known as combretabenzodiazepines. These compounds exhibit cytotoxic and antitubulin activity, which makes them promising candidates for the development of new anticancer drugs. The unique structure of combretabenzodiazepines allows them to target and disrupt the microtubules in cancer cells, thereby inhibiting their growth and proliferation.
In addition to its role in the synthesis of combretabenzodiazepines, 5-Methoxy-2-nitrobenzaldehyde may also be utilized in the development of other pharmaceutical compounds with potential therapeutic applications. Its reactivity and structural diversity make it a valuable tool in the design and synthesis of new molecules with specific biological activities.
Used in Chemical Research:
5-Methoxy-2-nitrobenzaldehyde can be employed as a research tool in various fields of chemistry, including organic synthesis, medicinal chemistry, and materials science. Its unique structure and reactivity make it an attractive candidate for the development of new synthetic methods, as well as for the study of reaction mechanisms and the exploration of novel chemical transformations.
In the field of materials science, 5-Methoxy-2-nitrobenzaldehyde may be used to develop new materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into polymers or other molecular structures could lead to the creation of advanced materials with potential applications in various industries, including electronics, energy, and environmental protection.

InChI:InChI=1/C8H7NO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5H,1H3

Upstream product

• 42454-06-8 2-nitro-5-hydroxybenzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 109005-38-1 4-methoxy-2-<<(4-methylphenyl)sulfonyl>methyl>-1-nitrobenzene 
• 74-88-4 methyl iodide 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 454466-57-0 methyl 3-formylphenyl carbonate 
• 5367-32-8 5-methoxy-2-nitrotoluene 
• 446-33-3 5-Fluoro-2-nitrotoluene 
• 100-83-4 meta-hydroxybenzaldehyde 
• 63932-00-3 5-methoxy-2-nitrobenzoyl chloride 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 879-55-0 (5-methoxy-2'-nitrophenyl)methanol 
• 7697-37-2 nitric acid 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 39755-95-8 5-methoxyisatine 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 10202-94-5 3-methoxy-2,6-dinitrobenzaldehyde 
• 860243-67-0 5-methoxy-2,4-dinitrobenzaldehyde 
• 26831-52-7 2-amino-5-methoxybenzaldehyde 
• 73428-02-1 5-methoxy-2-nitrobenzaldehyde ethylene acetal 
• 38469-84-0 2-nitro-5-methoxybenzonitrile 
• 142010-17-1 methyl (E)-3-(5′-methoxy-2′-nitrophenyl)acrylate 
• 612548-41-1 4-methoxy-1-nitro-2-[(E)-2-nitrovinyl]benzene 
• 596108-19-9 Z-(2-chloro-2-nitroethenyl)-5-methoxy-2-nitrobenzene 
• 908584-15-6 3-(5-methoxy-2-nitrophenyl)-2-(4-methoxyphenyl)propionitrile 
• 23842-82-2 2-amino-5-methoxybenzonitrile 
• 108047-38-7 2-(aminomethyl)-4-methoxyaniline 

Relevant articles and documents

Oligosaccharide synthesis on a light-sensitive solid support. I. The polymer and synthesis of isomaltose (6-O-alpha-D-glucopyranosyl-D-glucose).

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Synthesis of 5,10,15,20-tetrakis(2-amino-5-methoxyphenyl)-porphyrin: A versatile building block for porphyrin face selection

A new bis-faced substituted porphyrin has been prepared. The four hydroxyl groups on one side as well as the four amino functions on the other one allow at will, a different functionalization of each face of the macrocycle. The usefulness of this synthon is illustrated.

Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer

Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.

N, N ′-Disubstituted thiourea and urea derivatives: Design, synthesis, docking studies and biological evaluation against nitric oxide synthase

The synthesis and biological evaluation of new types of N,N′-disubstituted thiourea and urea derivatives as inhibitors of both neuronal nitric oxide synthase (nNOS) and inducible nitric oxide synthase (iNOS) are described. These compounds have been designed by reduction of the carbonyl group in the thiourea and urea kynurenamine derivatives 3 previously synthesized by our research group. The synthetic route performed to this new family also allows us to obtain the molecules 3 with less synthetic steps and higher global yield. Regarding the biological results, in general, the new derivatives 4a-q inhibit the neuronal NOS isoform better than the inducible one. Furthermore, thioureas exhibit higher inhibition than ureas for both isoenzymes. Among all the tested compounds, 4g shows significant nNOS (80.6%) and iNOS (76.6%) inhibition values without inhibiting eNOS. This molecule could be an interesting starting point for the design of new inhibitors with application in neurological disorders where both isoenzymes are implicated such as Parkinson's disease.