4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile

Base Information

• Chemical Name: 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile
• CAS No.: 236750-65-5
• Molecular Formula: C13H16N2O6
• Molecular Weight: 296.28
• Hs Code.: 2926909090
• UNII: QC2GR33BE6
• DSSTox Substance ID: DTXSID40581646
• Nikkaji Number: J1.797.778D
• Wikidata: Q72446181
• Mol file: 236750-65-5.mol

Synonyms:4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile;236750-65-5;BENZONITRILE, 4,5-BIS(2-METHOXYETHOXY)-2-NITRO-;4-5-bis(2-methoxyethoxy)-2-nitrobenzonitrile;QC2GR33BE6;SCHEMBL482018;DTXSID40581646;BCP08819;MFCD17676647;AKOS015895482;DS-18423;SY016026;2-Nitro-4,5-(2-methoxyethoxy)benzonitrile;AM20090615;CS-0150175;3,4-Bis(2-methoxyethoxy)-2-nitrobenzonitrile;4,5-Di(2-methoxyethoxy)-2-nitrobenzonitrile;4,5-bis-(2-Methoxyethoxy)-2-nitrobenzonitrile;A20678;F19335;J-514269;Benzonitrile, 4,5-bis(2-methoxyethoxy)-2-nitro-

Chemical Property of 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile

Chemical Property:

• Vapor Pressure: 1.28E-08mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 459.3oC at 760 mmHg
• Flash Point: 231.6oC
• PSA: 106.53000
• Density: 1.26g/cm3
• LogP: 2.04008
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 296.10083623
• Heavy Atom Count: 21
• Complexity: 363

Purity/Quality:

99% ^*data from raw suppliers

4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCOC1=C(C=C(C(=C1)C#N)[N+](=O)[O-])OCCOC
• Uses: 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile is an impurity of Erlotinib (E625008), a EGFR-targeted drug in the treatment of non-small cell lung cancer. EGFR small tyrosine kinase inhibitor that shows most substantial effect on tumor growth inhibition and animal survival.

Technology Process of 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile

There total 11 articles about 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.5%

3,4-bis(2-methoxyethoxy)-benzonitrile (80407-68-7) → 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile (236750-65-5)

Guidance literature:

With nitric acid; In dichloromethane; at 20 ℃; for 12h;

Reference yield:

3,4-bis(2-methoxyethoxy)benzaldehyde (80407-64-3) → 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile (236750-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydroxylamine hydrochloride; pyridine / methanol / Heating

2: acetic anhydride / 110 °C

3: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C

With pyridine; hydroxylamine hydrochloride; nitric acid; acetic anhydride; In methanol; acetic acid;

Reference yield:

3,4-dihydroxybenzonitrile (17345-61-8) → 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile (236750-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 70 °C

2: nitric acid / 48 h / 20 - 50 °C

With nitric acid; potassium carbonate; In N,N-dimethyl-formamide;

upstream raw materials:

3,4-bis(2-methoxyethoxy)-benzonitrile

C₁₃H₁₉NO₅

3,4-bis(2-methoxyethoxy)benzaldehyde

3,4-dihydroxybenzaldehyde

Downstream raw materials:

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

erlotinib hydrochloride

N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine

Refernces

• 1、 -. "Method for synthesizing erlotinib intermediate with microchannel reactor". Paragraph 0055; 0065; 0075; 0085; 0094-0099; 0102. . Retrieved 2018/09/08.
• 2、 -. "Method for preparing compound". Paragraph 0062; 0063; 0064; 0065. . Retrieved 2018/04/01.