5081-42-5

Basic information

• Product Name: Methyl 2-nitro-3,4,5-trimethoxybenzoate
• Synonyms: 2-Nitro-3,4,5-trimethoxybenzoic acid methyl ester;methyl 3,4,5-trimethoxy-2-nitrobenzoate;Methyl 2-nitrotrimethylgallate;3,4,5-Trimethoxy-2-nitrobenzoic acid methyl ester;Benzoic acid, 3,4,5-triMethoxy-2-nitro-, Methyl ester;Methyl 2-nitro-3,4,5-trimethoxybenzoate 98%;2-Nitro-3,4,5-trimethoxybenzoic acid methyl ester≥ 98% (GC);LABOTEST-BB LT00451972
• CAS NO: 5081-42-5
• Molecular Formula: C₁₁H₁₃NO₇
• Molecular Weight: 271.22
• EINECS: 225-794-8
• Product Categories: Aromatic Esters;C10 to C11;Carbonyl Compounds;Esters
• Mol File: 5081-42-5.mol

Chemical Properties

• Melting Point: 67-69°C
• Boiling Point: 420°Cat760mmHg
• Flash Point: 188.9°C
• Appearance: /
• Density: 1.284g/cm³
• Vapor Pressure: 2.9E-07mmHg at 25°C
• Refractive Index: 1.523
• BRN: 2702653
• CAS DataBase Reference: Methyl 2-nitro-3,4,5-trimethoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-nitro-3,4,5-trimethoxybenzoate(5081-42-5)
• EPA Substance Registry System: Methyl 2-nitro-3,4,5-trimethoxybenzoate(5081-42-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5081-42-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Methyl 2-nitro-3,4,5-trimethoxybenzoate is used as an intermediate in the chemical synthesis of various compounds, particularly in the preparation of 2-nitro-3,4,5-trimethoxybenzoic acid. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2-nitro-3,4,5-trimethoxybenzoate is used as a key component in the development of new drugs. Its chemical properties enable it to be a versatile starting material for the synthesis of various drug candidates, potentially leading to the discovery of novel therapeutic agents with improved efficacy and safety profiles.
Used in Research and Development:
Methyl 2-nitro-3,4,5-trimethoxybenzoate is also utilized in research and development settings, where it serves as a model compound for studying the reactivity and properties of similar organic molecules. This helps researchers gain a deeper understanding of the underlying chemical mechanisms and paves the way for the design of more effective and targeted drugs.

InChI:InChI=1/C11H13NO7/c1-16-7-5-6(11(13)19-4)8(12(14)15)10(18-3)9(7)17-2/h5H,1-4H3

Upstream product

• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 66907-52-6 3,4,5-trimethoxy-2-nitrobenzoic acid 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 7782-77-6 cis-nitrous acid 
• 118-41-2 Eudesmic acid 

Downstream Products

• 5035-82-5 methyl 3,4,5-trimethoxyanthranilate 
• 66907-52-6 3,4,5-trimethoxy-2-nitrobenzoic acid 
• 100450-59-7 2-Amino-3,4,5-trimethoxy-benzoesaeure-isopropylester 
• 61948-85-4 3,4,5-trimethoxyanthranilic acid 
• 116274-49-8 2-<(aminocarbonyl)amino>-3,4,5-trimethoxybenzoic acid 
• 30896-98-1 6,7,8-trimethoxy-2,4-(1H,3H)-quinazolinedione 
• 860518-52-1 1,2,3-trimethoxy-4,5-dinitro-benzene 
• 52978-82-2 2-Nitro-3,4,5-trimethoxy-benzylchlorid 
• 103387-07-1 2-nitro-3,4,5-trimethoxybenzyl bromide 
• 108984-62-9 1-(3'-Methoxy-phenyl)-3-(2'-nitro-3',4',5'-trimethoxy-phenyl)-propanol 
• 102458-13-9 Bis-<2-nitro-3,4,5-trimethoxybenzyl>-aether 
• 5435-28-9 (3,4,5-trimethoxy-2-nitrophenyl)methanol 
• 101585-71-1 2-Nitro-3,4,5-trimethoxy-benzyl-p-toluolsulfonsaeureester 
• 110049-40-6 1-(3-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propan-1-one 

Relevant articles and documents

PDIA4 INHIBITORS AND USE THEREOF FOR INHIBITING ?-CELL PATHOGENESIS AND TREATING DIABETES

Disulfide-Isomerase A4 (PDIA4) inhibitors and use thereof for inhibiting pancreatic β-cell pathogenesis and treating diabetes are disclosed. Drug candidates that inhibit PDIA4 with IC50 values ranging from 4 μM to 300 nM are identified. The compounds are highly active in augmenting insulin secretion from pancreatic β-cells. The representative compound No. 8 (4,5-dimethoxy-2-propiolamidobenzoic acid), alone or in combination with metformin, is effective in preserving pancreatic β-cell function, treating and/or reversing, returning blood glucose concentration to a normal level in a diabetic.

Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives

A series of 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds of Tg1–14 were found to inhibit SGC7901 cell proliferation, and compound Tg11 (IC50 = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC50 = 5.16 μM). This suggests that compound Tg11 can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot analysis showed that treatment with Tg11 (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that Tg11 is a potential anticancer agent capable of inhibiting cell proliferation.

Synthesis, biological evaluation and molecular docking studies of 2-amino-3,4,5-trimethoxyaroylindole derivatives as novel anticancer agents

A series of novel 2-amino-3,4,5 trimethoxyaroylindole derivatives was synthesized and evaluated against selected human cancer cell lines of breast (MCF-7) and colon (HT-29). Introduction of an amino group at the C-2 position on ring A of 3,4,5-trimethoxyaroylindole derivatives resulted in novel compounds, i.e., 2-amino-3,4,5-trimethoxyaroylindole derivatives exhibiting excellent cytotoxic activity against human cancer cell lines. Substitution with methoxy group at R6 in 2-amino-3,4,5-trimethoxyaroylindole 5d exhibited excellent cytotoxic activity against MCF-7 (0.013 μM) and colon HT-29 (0.143 μM) indicating slightly higher potency than Combretastatin A-4. Molecular modeling studies of 2-amino-3,4,5-trimethoxyaroylindole derivatives have similar structural alignment as colchicine in protein (PDB code: 1SA0) and exhibited hydrogen bond interaction between para position of 3,4,5-trimethoxyphenyl ring with CYS 241 and N-H molecule of indole ring with Val 315 of receptor molecule.

Design and application of a rigid quinazolone scaffold based on two-face Bim α-helix mimicking

Based on our previous discovery of an anthraquinone scaffold mimicking two faces of Bim α-helix, we derived a quinazolone scaffold through structure simplification and optimization. It was inferred that a rigid bicyclic ring was necessary and efficient to maintain the two-faced binding mode. A novel dual inhibitor 6c [6,7,8-trihydroxy-3-(2-hydroxy-5-methylbenzyl)-2-phenylquinazolin- 4(3H)-one] was obtained based on this scaffold. 6c exhibited dual binding activity with Ki values of 0.123 μM for Mcl-1 and 0.179 μM for Bcl-2.

Microwave assisted synthesis of novel 6,7,8-trimethoxy N-substituted-4- aminoquinazoline compounds

(Chemical Equation Presented) A fast, efficient and convenient reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl (or benzyl) amines was achieved under microwave irradiation in isopropyl alcohol, providing a simple method for synthesis of novel 6,7,8-trimethoxy N-substituted-4-aminoquinazoline compounds in good yield in short time. The title compounds were evaluated for their in vitro anti-proliferative activities against PC3 cell by MTT method.

Synthesis and bioactivities of 6,7,8-trimethoxy-N-aryl-4-aminoquinazoline derivatives

A series of 4-aminoquinazoline derivatives is prepared by the nucleophilic substitution reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl amine. The structures of the compounds are confirmed by elemental analysis, IR, and 1H NMR spectral data. The compounds are also evaluated for their ability to inhibit tumor cells PC3, A431, Bcap-37, and BGC823 by MTT assays. Among them, 6b and 6e are found as potent inhibitors, with IC50 values ranging from 5.8 to 9.8 μM, in vitro assay.

Synthesis and biological activity of novel N-substituted 4-amino-6,7,8-trimethoxyquinazoline compounds

A series of N-substituted 4-amino-6,7,8-trimethoxyquinazoline derivatives has been synthesized from 4-chloro-6,7,8-trimethoxyquinazoline and aryl (or benzyl) amines using 2-propanol as a solvent. The starting material 4-chloro-6,7,8-trimethoxyquinazoline has been synthesized from natural gallic acid by a novel route. Their structures have been verified by elemental analysis and IR, 1H, and 13C NMR spectroscopy. The title compounds have been evaluated for their in vitro antiproliferative activities against some cancer cells by the MTT method. Unfortunately, most of the compounds tested have exhibited a weaker anticancer activity than the reference standard drug PD153035.

A mild and efficient method for the mononitration of aromatic compounds by cerium (III) ammonium nitrate in acetic anhydride

A mild and efficient method for the mononitration of aromatic and olefinic compounds is described. This method is especially useful for active substrates.

Cyclic diamine compound with condensed-ring groups

A cyclic diamine compound of formula (1): wherein R1 and R2 are individually a hydrogen atom or a methoxy group, provided R1 is a methoxy group when R2 is a hydrogen atom, or a hydrogen atom when R2 is a methoxy group; A is an oxygen atom, a sulfur atom, CH═CH, CH═N or NR3, in which R3 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; B is a nitrogen atom, CH or CR4, in which R4 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; m is 1 or 2; and n is a number of 1 to 5, an acid-addition salt thereof, or a hydrate thereof. The compound has inhibitory effects on cell adhesion and is useful for treatment of allergy, asthma, rheumatism, arteriosclerosis, and inflammation.

2-(Piperazinyl)-4-pyrimioinamines

Herein is disclosed 2-(1-piperazinyl)-4-pyrimidinamine derivatives, acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives. The derivatives are distinguished most readily by having novel substituents at position 4 of the piperazinyl radical, the substituents being selected from the group consisting of optionally substituted 2-cycloheptimidazolyl, 1,4,5,6,7,8-hexahydrocycloheptimidazol-2-yl, 2-benzoxazolyl, benzthiazol-2-yl, 1H-2-benzimidazolyl and 1-oxo-2,4,6-cycloheptarien-2-yl. The derivatives are useful for treating hypertension in a mammal.