100905-33-7

Basic information

• Product Name: ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE
• Synonyms: LABOTEST-BB LT00848060;ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE;RARECHEM AL BI 0187;4,5-Dimethoxy-2-nitrobenzoic acid ethyl ester~Ethyl 3,4-dimethoxy-6-nitrobenzoate~Ethyl 6-nitroveratrate;4,5-Dimethoxy-2-nitrobenzoicacidethylester~Ethyl3,4-dimethoxy-6-nitrobenzoate~Ethyl6-nitroveratrate;4,5-dimethoxy-2-nitrobenzoic acid ethyl ester;ethyl 3,4-dimethoxy-6-nitrobenzoate;Ethyl 4,5-dimethoxy-2-nitrobenzoate, 98+%
• CAS NO: 100905-33-7
• Molecular Formula: C₁₁H₁₃NO₆
• Molecular Weight: 255.22
• Mol File: 100905-33-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 392.3°Cat760mmHg
• Flash Point: 174.7°C
• Appearance: /
• Density: 1.253
• Vapor Pressure: 2.31E-06mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: 2-8°C
• BRN: 2699210
• CAS DataBase Reference: ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE(100905-33-7)
• EPA Substance Registry System: ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE(100905-33-7)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 100905-33-7(Hazardous Substances Data)

Usage

General Description

ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE is a chemical compound with the molecular formula C11H13NO6. It is an ester derivative of 4,5-dimethoxy-2-nitrobenzoic acid, with an ethyl group attached to the oxygen atom. This chemical is often used in the synthesis of pharmaceuticals and agrochemicals due to its nitro and ester functional groups. It has a yellow color and is insoluble in water but soluble in organic solvents. ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE is known for its potential use as an intermediate in the preparation of various derivatives and is often used in research and development processes.

InChI:InChI=1/C11H13NO6/c1-4-18-11(13)7-5-9(16-2)10(17-3)6-8(7)12(14)15/h5-6H,4H2,1-3H3

Upstream product

• 93-07-2 Veratric acid 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 64-17-5 ethanol 
• 100905-32-6 phenyl 2-nitro-4,5-dimethoxybenzoate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 3943-77-9 ethyl veratrate 

Downstream Products

• 860540-41-6 3-(4,5-dimethoxy-2-nitro-phenyl)-3-oxo-propionic acid ethyl ester 
• 808762-63-2 4-((4-bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol 

Relevant articles and documents

Synthesis and evaluation of novel 18F-labeled quinazoline derivatives with low lipophilicity for tumor PET imaging

Four novel 18F-labeled quinazoline derivatives with low lipophilicity, [18F]4-(2-fluoroethoxy)-6,7-dimethoxyquinazoline ([18F]I), [18F]4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine ([18F]II), [18F]4-(2-fluoroethoxy)-7-methoxy-6-(2-methoxyethoxy)quinazoline ([18F]III), and [18F]4-(2-fluoroethoxy)-6,7-bis(2-methoxyethoxy)quinazoline ([18F]IV), were synthesized via a 2-step radiosynthesis procedure with an overall radiochemical yield of 10% to 38% (without decay correction) and radiochemical purities of >98%. The lipophilicity and stability of labeled compounds were tested in vitro. The log P values of the 4 radiotracers ranged from 0.52 to 1.07. We then performed ELISA to measure their affinities to EGFR-TK; ELISA assay results indicated that each inhibitor was specifically bounded to EGFR-TK in a dose-dependent manner. The EGFR-TK autophosphorylation IC50 values of [18F]I, [18F]II, [18F]III, and [18F]IV were 7.732, 0.4698, 0.1174, and 0.1176?μM, respectively. All labeled compounds were evaluated via cellular uptake and blocking studies in HepG2 cell lines in vitro. Cellular uptake and blocking experiment results indicated that [18F]I and [18F]III had excellent cellular uptake at 120-minute postinjection in HepG2 carcinoma cells (51.80?±?3.42%ID/mg protein and 27.31?±?1.94%ID/mg protein, respectively). Additionally, biodistribution experiments in S180 tumor-bearing mice in vivo indicated that [18F]I had a very fast clearance in blood and a relatively high uptake ratio of tumor to blood (4.76) and tumor to muscle (1.82) at 60-minute postinjection. [18F]III had a quick clearance in plasma, and its highest uptake ratio of tumor to muscle was 2.55 at 15-minute postinjection. These experimental results and experiences were valuable for the further exploration of novel radiotracers of quinazoline derivatives.

Facile Synthesis of Novel Perfluorocarbon-Modulated 4-Anilinoquinazoline Analogues

4-Anilinoquinazoline analogues stand out among many kinds of small molecules that inhibit the tyrosine kinase activities of epidermal growth factor receptor (EGFR), thus serving as significant molecular targets for anticancer drug design. Herein, a series of novel perfluorocarbon (PFC) modulated 4-anilinoquinazolines were designed and prepared straightforwardly by nucleophilic substitution reaction of various anilinoquinazolines and PFC-derived methanesulfonate. In the presence of base, the reaction proceeded smoothly to afford a wide range of 4-anilinoquinazolines with different substituents on aniline moiety in good to high yields. Furthermore, the PFC-modified analogues of gefitinib and erlotinib were also obtained in 93% and 90% respectively, which may have potential for developing new inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase and fluorinated contrast agents (CA) for 19F MRI.

Model 18 F mark substituted [...] compound and its preparation method and tumor PET imaging applications

The invention provides a novel F marked substituted quinazoline compound. The novel F marked substituted quinazoline compound is characterized in that one end of the novel F marked substituted quinazoline compound has a F substituted alkyloxy structure; the other end of the compound has a 6,7-substituted quinazoline structure, and a substituent R1 is positioned in the 4 position of a quinazoline maternal, and is a 2-, 3-, 4-F substituted alkyloxy group; and a substituent R2 is positioned in the 6 position of the quinazoline maternal, and is a methoxyethoxy group, a methoxy group, or a morpholinepropanolato group. The structural formula of the compound is shown as A in the specification. Results of experiments show that the compound has the advantages of good bioactivity, good serum stability, low intake in tissues of the liver and the like, and high enrichment and slow removal rate in tumors, and the marking precursor of the compound has the advantages of easy synthesis, extremely high marking rate and the like, so the compound has a huge potential for the tumor PET development.