26510-91-8

Basic information

• Product Name: 2,4,5-Trimethoxyaniline
• Synonyms: 2,4,5-Trimethoxyaniline;5-AMINO-1,2,4-TRIMETHOXYBENZENE
• CAS NO: 26510-91-8
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.2
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 26510-91-8.mol

Chemical Properties

• Melting Point: 93-95 °C
• Boiling Point: 305.5°C at 760 mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 1.118g/cm³
• Vapor Pressure: 0.000817mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.72±0.10(Predicted)
• CAS DataBase Reference: 2,4,5-Trimethoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trimethoxyaniline(26510-91-8)
• EPA Substance Registry System: 2,4,5-Trimethoxyaniline(26510-91-8)

Safety Data

• Hazardous Substances Data: 26510-91-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4,5-Trimethoxyaniline is used as a key intermediate in the synthesis of Quinoline-5,8-dione derivatives, which are known as TGase 2 inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, including cancer and autoimmune disorders. The compound's unique structure allows for the formation of these therapeutically relevant derivatives, making it a valuable component in the pharmaceutical sector.

InChI:InChI=1/C9H13NO3/c1-11-7-5-9(13-3)8(12-2)4-6(7)10/h4-5H,10H2,1-3H3

Upstream product

• 14227-14-6 1,2,4-trimethoxy-5-nitrobenzene 
• 292037-88-8 N-(2',4',5'-trimethoxyphenyl)-4-cyano-2,5-dimethylacetanilide 
• 20129-11-7 1-bromo-2,4,5-trimethoxybenzene 
• 1137558-16-7 benzyl 2,4,5-trimethoxyphenylcarbamate 
• 4460-86-0 asaraldehyde 
• 135-77-3 1,2,4-trimethoxy-benzene 

Downstream Products

• 3117-03-1 2,5-dimethoxyquinone 
• 7107-04-2 2-amino-4,5-dimethoxyphenol 
• 804476-57-1 N-(2,4,5-trimethoxyphenyl)benzamide 
• 6046-71-5 4-hydroxy-5,6,8-trimethoxy-quinoline-2-carboxylic acid ethyl ester 
• 140112-57-8 (Z)-Octadec-9-enoic acid (2,4,5-trimethoxy-phenyl)-amide 
• 116614-93-8 ethyl 6-chloro-3-(2,4,5-trimethoxyphenylamino)hex-2-enoate 
• 116614-92-7 ethyl (E)-(1-(2,4,5-trimethoxyphenyl)-2-pyrrolidinylidene)acetate 
• 80270-97-9 (E)-3-(2,4,5-Trimethoxy-phenylamino)-but-2-enoic acid ethyl ester 
• 152532-10-0 3-oxo-N-(2,4,5-trimethoxyphenyl)butanamide 
• 96938-57-7 N-benzoyl-N'-(2,4,5-trimethoxyphenyl)thiourea 
• 80270-90-2 (E)-4-(2,4,5-Trimethoxy-phenylamino)-pent-3-en-2-one 
• 132555-48-7 4-Chloro-N-(2,4,5-trimethoxyphenyl)butanamide 
• 30072-74-3 N-(2-Diethylamino-ethyl)-N',N'-diethyl-N-(2,4,5-trimethoxy-phenyl)-ethane-1,2-diamine 
• 170959-09-8 2,4,5-trimethoxypivaloylaminobenzene 

Relevant articles and documents

Methoxy and bromo scans on N-(5-methoxyphenyl) methoxybenzenesulphonamides reveal potent cytotoxic compounds, especially against the human breast adenocarcinoma MCF7 cell line

Thirty seven N-(5-methoxyphenyl)-4-methoxybenzenesulphonamide with methoxy or/and bromo substitutions (series 1-4) and with different substituents on the sulphonamide nitrogen have been synthesised. 21 showed sub-micromolar cytotoxicity against HeLa and HT-29 human tumour cell lines, and were particularly effective against MCF7. The most potent series has 2,5-dimethoxyanilines, especially the 4-brominated compounds 23–25. The active compounds inhibit microtubular protein polymerisation at micromolar concentrations, thus pointing at tubulin as the target. Co-treatment with the MDR inhibitor verapamil suggests that they are not MDR substrates. Compound 25 showed nanomolar antiproliferative potency. It severely disrupts the microtubule network in cells and arrests cells at the G2/M cell-cycle phase, thus confirming tubulin targeting. 25 triggered apoptotic cell death, and induced autophagy. Docking studies suggest binding in a distinct way to the colchicine site. These compounds are promising new antitumor agents acting on tubulin.

Method of preparing Quinoline-5,8-dione derivatives for TGase 2 inhibitor

I Is -5,8- of the quinoline, dione derivative compound. of Formula I, or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein the compound of Formula, TGase 2 has, inhibitory effects TGase 2, and thus the pharmaceutical composition may be useful for preventing or treating disorders or diseases mediated by TGase 2 or inhibiting. (by machine translation)

Quinoline-5,8-dione derivatives for TGase 2 inhibitor, and the pharmaceutical composition comprising the same

The present invention relates to a quinolin-5,8-dione derivative compound represented by chemical formula I, an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound represented by chemical formula I of the present invention has a TGase 2 inhibitory effect, and the pharmaceutical composition comprising the same can be usefully used for preventing or treating disorders or diseases mediated by TGase 2 or response to TGase 2 inhibition.COPYRIGHT KIPO 2020

Synthesis method of 2,4,5-trimethoxybenzeneamine

The invention discloses a synthesis method of 2,4,5-trimethoxybenzeneamine, and especially uses a palladium-carbon catalyst to synthesize 2,4,5-trimethoxybenzeneamine. The method is characterized in that a reaction mixture and hydrogen are contacted to fo

2-Aroylquinoline-5,8-diones as potent anticancer agents displaying tubulin and heat shock protein 90 (HSP90) inhibition

This study reports the synthesis of a series of 2-aroylquinoline-5,8-diones (11-23) on the basis of scaffold hopping. The presence of a methoxy group at C6 assists the highly regioselective incorporation with various amines, and simplifies the structural

Total synthesis of the antitumor antibiotic (±)-streptonigrin: First- and second-generation routes for de novo pyridine formation using ring-closing metathesis

The total synthesis of (±)-streptonigrin, a potent tetracyclic aminoquinoline-5,8-dione antitumor antibiotic that reached phase II clinical trials in the 1970s, is described. Two routes to construct a key pentasubstituted pyridine fragment are depicted, both relying on ring-closing metathesis but differing in the substitution and complexity of the precursor to cyclization. Both routes are short and high yielding, with the second-generation approach ultimately furnishing (±)-streptonigrin in 14 linear steps and 11% overall yield from inexpensive ethyl glyoxalate. This synthesis will allow for the design and creation of druglike late-stage natural product analogues to address pharmacological limitations. Furthermore, assessment of a number of chiral ligands in a challenging asymmetric Suzuki-Miyaura cross-coupling reaction has enabled enantioenriched (up to 42% ee) synthetic streptonigrin intermediates to be prepared for the first time.

Total synthesis of (±)-streptonigrin: De novo construction of a pentasubstituted pyridine using ring-closing metathesis

The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities

An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

Total synthesis of streptonigrone

(Chemical Equation Presented) A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad-Limpach reaction, rather than the customary Friedlaender methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.