52978-83-3

Basic information

• Product Name: 2,3,4-TRIMETHOXY-6-NITROBENZALDEHYDE
• Synonyms: 2,3,4-TRIMETHOXY-6-NITROBENZALDEHYDE
• CAS NO: 52978-83-3
• Molecular Formula: C₁₀H₁₁NO₆
• Molecular Weight: 241.2
• Mol File: 52978-83-3.mol

Chemical Properties

• Boiling Point: 425.078 °C at 760 mmHg
• Flash Point: 203.646 °C
• Appearance: /
• Density: 1.304 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 2,3,4-TRIMETHOXY-6-NITROBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRIMETHOXY-6-NITROBENZALDEHYDE(52978-83-3)
• EPA Substance Registry System: 2,3,4-TRIMETHOXY-6-NITROBENZALDEHYDE(52978-83-3)

Safety Data

• Hazardous Substances Data: 52978-83-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-Trimethoxy-6-nitrobenzaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals. Its chemical structure allows for the development of new drug molecules, contributing to the advancement of medical treatments.
Used in Dye Industry:
In the dye industry, 2,3,4-Trimethoxy-6-nitrobenzaldehyde is used as an intermediate for the production of dyes. Its chemical properties enable the creation of a wide range of colorants for various applications, such as textiles, plastics, and printing inks.
Used in Organic Compounds Synthesis:
2,3,4-Trimethoxy-6-nitrobenzaldehyde is used as a building block in the synthesis of other organic compounds. Its versatile structure allows for the development of new chemical entities with potential applications in various fields, including materials science and chemical research.
Used in Fragrance Industry:
2,3,4-Trimethoxy-6-nitrobenzaldehyde is used as a fragrance ingredient due to its aromatic properties. It contributes to the creation of complex and pleasant scents for use in perfumes, cosmetics, and personal care products.
Used in Food Flavoring Industry:
In the food flavoring industry, 2,3,4-Trimethoxy-6-nitrobenzaldehyde is used to enhance the flavor of various food products. Its aromatic characteristics allow for the development of unique and appealing taste profiles, adding value to food and beverage offerings.

InChI:InChI=1/C10H11NO6/c1-15-8-4-7(11(13)14)6(5-12)9(16-2)10(8)17-3/h4-5H,1-3H3

Upstream product

• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Downstream Products

• 137920-33-3 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 137920-34-4 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 142004-00-0 2-hydroxy-1-nitro-3,4,5-trimethoxybenzene 
• 823829-22-7 2,3,4-trimethoxy-6-(4-methoxy-benzylsulfanyl)-benzaldehyde 
• 30448-04-5 4,5,6-trimethoxy-1H-indole 
• 145182-61-2 2-methyl-3,4,5-trimethoxyaniline 
• 82358-34-7 coeloginin 
• 1360789-67-8 methyl 2-hydroxy-6-iodo-3,4-dimethoxybenzoate 
• 1752-02-9 methyl 6-iodo-2,3,4-trimethoxybenzoate 
• 1334162-97-8 6-iodo-2,3,4-trimethoxybenzoic acid 
• 1448816-22-5 (6-(2-hydroxy-4-methoxyphenyl)-1H-tetrazol-1-yl)-2,3,4-trimethoxyphenol 
• 1448816-31-6 2-(benzyloxy)-N-(2-(benzyloxy)-3,4,5-trimethoxyphenyl)-4-methoxybenzamide 
• 1448816-30-5 2-(benzyloxy)-3,4,5-trimethoxyaniline 
• 1448816-27-0 2-(benzyloxy)-3,4,5-trimethoxy-1-nitrobenzene 

Relevant articles and documents

Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.

Rapid access to Asp/Glu sidechain hydrazides as thioester precursors for peptide cyclization and glycosylation

Head-to-sidechain macrocylic peptides, and neoglycopeptides, were readily prepared by site-specific amidation of aspartic and glutamic acid sidechain hydrazides. Hydrazides, serving as latent thioesters, were introduced through regioselective opening of the corresponding Nα-Fmoc protected anhydride precursors.

Thiadiazoline- And pyrazoline-based carboxamides and carbothioamides: Synthesis and inhibition against nitric oxide synthase

Two new families of pyrazoline and thiadiazoline heterocycles have been developed. Their inhibitory activities against two different isoforms of nitric oxide synthase (inducible and neuronal NOS) are reported. The novel derivatives were synthesized combining the arylthiadiazoline or arylpyrazoline skeleton and a carboxamide or carbothioamide moiety, used as starting material ethyl 2-nitrobenzoates or substituted nitrobenzaldehydes, respectively. The structure-activity relationships of final molecules are discussed in terms of the R1 radical effects in the aromatic ring, the Y atom in the heterocyclic system, the X heteroatom in the main chain, and the R2 substituent in the carboxamide or carbothioamide rest. In general, thiadiazolines (5a-e) inhibit preferentially the neuronal isoform; among them, 5a is the best nNOS inhibitor (74.11% at 1 mM, IC50 = 420 M). In contrast, pyrazolines (6a-r) behave better as iNOS than nNOS inhibitors, 6m being the best molecule of this series (76.86% at 1 mM of iNOS inhibition, IC50 = 130 M) and the most potent of all tested compounds.

Polycationic ligands in gold catalysis: Synthesis and applications of extremely π-acidic catalysts

Very often ligands are anionic or neutral species. Cationic ones are rare, and, when used, the positively charged groups are normally appended to the periphery of the ligand. Here, we describe a dicationic phosphine with no spacer between the phosphorus atom and the two positively charged groups. This structural feature makes its donor ability poorer than that of phosphites and only comparable to extremely toxic or pyrophoric compounds such as PF 3 or P(CF3)3. By exploiting these properties, a new Au catalyst has been developed displaying a dramatically enhanced capacity to activate π-systems. This has been used to synthesize very sterically hindered and naturally occurring 4,5-disubstituted phenanthrenes. The present approach is expected to be applicable to the development and improvement of many other transition metal catalyzed transformations that benefit from extremely strong π-acceptor ligands. The mechanism of selected catalytic transformations has been explored by density functional calculations.

Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In gener

Correlation of hydrogen-bonding propensity and anticancer profile of tetrazole-tethered combretastatin analogues

A series of 1,5-disubstituted tetrazole-tethered combretastatin analogues with extended hydrogen-bond donors at the ortho-positions of the aryl A and B rings were developed and evaluated for their antitubulin and antiproliferative activity. We wanted to test whether intramolecular hydrogen-bonding used as a conformational locking element in these analogues would improve their activity. The correlation of crystal structures with the antitubulin and antiproliferative profiles of the modified analogues suggested that hydrogen-bond-mediated conformational control of the A ring is deleterious to the bioactivity. In contrast, although there was no clear evidence that intramolecular hydrogen bonding to the B ring enhanced activity, we found that increased substitution on the B ring had a positive effect on antitubulin and antiproliferative activity. Among the various analogues synthesized, compounds 5d and 5e, having hydrogen-bonding donor groups at the ortho and meta-positions on the 4-methoxy phenyl B ring, are strong inhibitors of tubulin polymerization and antiproliferative agents having IC50 value in micromolar concentrations.

Nucleophilic substitution of nitro groups by [18F]fluoride in methoxy-substituted ortho-nitrobenzaldehydes-A systematic study

As model reactions for the introduction of [18F]fluorine into aromatic amino acids, the replacement of NO2 by [18F]fluoride ion in mono- to tetra-methoxy-substituted ortho-nitrobenzaldehydes was systematically investigated. Unexpectedly, the highly methoxylated precursors 2,3,4-trimethoxy-6-nitrobenzaldehyde and 2,3,4,5-tetramethoxy-6-nitrobenzaldehyde showed high maximum radiochemical yields (82% and 48% respectively). When the electrophilicity of the leaving group substituted carbon atom is expressed by its 13C NMR chemical shift a good correlation with the reaction rate at the beginning of the reaction (first min) was found (R2 = 0.89), whereas the maximum radiochemical yields correlated much poorer with this electrophilicity parameter. This may be caused by side reactions becoming influencial in the further reaction course. As possible side reactions the demethylation of methoxy groups and intramolecular redox reactions could be detected by HPLC/MS.

Compounds interacting with tubulin: Part I: Synthesis of ortho-ortho' substituted phenylpyrroles with free or restricted rotation.

The synthesis of ortho-ortho' substituted phenylpyrroles that are susceptible to isomerization of the biaryl type (atropisomerism) was performed using a Michael addition of isocyanoacetates with nitrostyrenes.Atropisomerism in phenylpyrroles 14 and 15 was studied by means of 1H NMR spectroscopy using chiral lanthanide shift reagents (LSR*).In the case of chiral phenylpyrrole 21, an evaluation of the interconversion parameters between diastereomers (k, ΔGT*) was attempted. - - - tubulin / phenylpyrrole / atropisomers / chiral shift reagents