179688-26-7

Basic information

• Product Name: Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate
• Synonyms: 4,5-Bis(2-methoxyethoxy)-2-nitrobenzoic acid ethyl ester;Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate;Methyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate;Erlotinib interMidiate III;Benzoic acid,4,5-bis(2-Methoxyethoxy)-2-nitro-, ethyl ester;Erlotinib Impurity 6;179688-26-7;4,5-bis(2-methoxyethoxy)-2-nitrobenzoate
• CAS NO: 179688-26-7
• Molecular Formula: C₁₅H₂₁NO₈
• Molecular Weight: 343.32914
• EINECS: 1312995-182-4
• Product Categories: Erlotinib INTERMEDIATES
• Mol File: 179688-26-7.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 467.8 °C at 760 mmHg
• Flash Point: 185.6 °C
• Appearance: /
• Density: 1.215
• Vapor Pressure: 6.29E-09mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate(179688-26-7)
• EPA Substance Registry System: Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate(179688-26-7)

Safety Data

• Hazardous Substances Data: 179688-26-7(Hazardous Substances Data)

Usage

Description

Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate is an organic compound that serves as an important intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its nitrobenzoate structure and the presence of two methoxyethoxy groups attached to the 4 and 5 positions of the benzene ring.

Uses

Used in Pharmaceutical Industry:
Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate is used as a key intermediate in the synthesis of 4-(indol-3-yl)quinazolines, which are epidermal growth factor receptor tyrosine kinase inhibitors. These inhibitors play a crucial role in the development of targeted therapies for cancer treatment.
Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate is also used in the preparation of Erlotinib hydrochloride (E625000), a drug that has shown significant efficacy in the treatment of non-small cell lung cancer. Its role in the synthesis of Erlotinib hydrochloride highlights its importance in the development of life-saving medications for cancer patients.

InChI:InChI=1/C15H21NO8/c1-4-22-15(17)11-9-13(23-7-5-20-2)14(24-8-6-21-3)10-12(11)16(18)19/h9-10H,4-8H2,1-3H3

Upstream product

• 183322-16-9 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester 
• 3943-89-3 Ethyl protocatechuate 
• 7732-18-5 water 
• 584-08-7 potassium carbonate 
• 6482-24-2 2-Bromoethyl methyl ether 
• 819813-71-3 3,4-bis(2-methoxyethoxy)-benzoic acid 
• 627-42-9 2-chloroethyl methyl ether 
• 99-50-3 3,4-Dihydroxybenzoic acid 

Downstream Products

• 179688-27-8 ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate 
• 179688-29-0 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one 
• 183322-18-1 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline 
• 183319-69-9 erlotinib hydrochloride 
• 179688-29-0 6,7-bis-(2-methoxyethoxy)-4(3H)quinazolinone 
• 1347720-70-0 C₂₁H₂₄ClN₃O₅ 
• 1347720-73-3 C₂₁H₂₄BrN₃O₅ 
• 1347720-76-6 C₂₁H₂₄FN₃O₅ 
• 1347720-82-4 C₂₁H₂₄N₄O₇ 
• 1347720-89-1 C₂₂H₂₄F₃N₃O₅ 
• 1347719-48-5 N-{2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline}benzamide 
• 1347720-93-7 C₂₁H₂₃ClFN₃O₅ 
• 1347721-06-5 C₂₂H₂₆ClN₃O₅ 
• 1347720-85-7 C₂₂H₂₄N₄O₅ 

Relevant articles and documents

Synthetic method of erlotinib

The invention relates to a synthetic method of erlotinib, and belongs to the technical field of chemical synthesis. The preparation method comprises the following synthesis steps: (1) reacting a compound I with 2-chloroethyl methyl ether to generate a compound II; (2) oxidizing the compound II through peracetic acid to generate a compound III; (3) reacting the compound III with benzene sulfonyl chloride to generate a compound IV; (4) carrying out a ring closing reaction on the compound IV, ammonium chloride and formamide to generate a compound V; (5) reacting the compound V with phosphorus oxychloride to generate a compound VI; and (6) reacting the compound VI with m-aminophenylacetylene to generate a compound VII erlotinib. The invention provides a new synthetic route, and the used raw materials are common materials, are simple and easily available, can adapt to production of various scales, and the synthetic method has good industrial production prospects.

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.

Preparation method of 4,-5-bis(2-methoxyl ethyoxyl)-2-ethyl nitrobenzoate

The invention relates to a preparation method of 4,-5-bis(2-methoxyl ethyoxyl)-2-ethyl nitrobenzoate. The preparation method comprises the following steps: (1) enabling 4,5-dihydroxy ethyl benzoate to react with a protective agent, then reacting with nitr