2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile

Base Information

• Chemical Name: 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile
• CAS No.: 950596-58-4
• Molecular Formula: C13H18N2O4
• Molecular Weight: 266.297
• Hs Code.: 2926909090
• Mol file: 950596-58-4.mol

Synonyms:QC-8358;2-amino-4,5-bis(2-methoxyethoxy)-benzonitrile;ethyl2-amino-4,5-bis(2-methoxyethoxy)-2-aminobenzoate;2-cyano-4,5-dimethoxyethoxylaniline;BENZONITRILE,2-AMINO-4,5-BIS(2-METHOXYETHOXY);

Chemical Property of 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile

Chemical Property:

• Melting Point: 73-77 °C
• Boiling Point: 445.5±45.0 °C(Predicted)
• PKA: 1.85±0.10(Predicted)
• PSA: 86.73000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 1.77208
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-((4-Chloro-7-(2-methoxyethoxy)quinazolin-6-yl)oxy)ethanol is an impurity if Erlotinib (E625008) a EGFR-targeted drug in the treatment of non-small cell lung cancer. 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile 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 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile

There total 6 articles about 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile 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: 95.0%

4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile (236750-65-5) → 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile (950596-58-4)

Guidance literature:

With sodium dithionite; In water; at 50 ℃; for 2.5h;

DOI:10.1021/op700054p

Reference yield:

3,4-bis(2-methoxyethoxy)-benzonitrile (80407-68-7) → 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile (950596-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nitric acid / acetic acid / 4 h / 0 °C

2.1: sodium dithionite / water / 3 h / 50 °C

2.2: 0.5 h / 65 °C

With sodium dithionite; nitric acid; In water; acetic acid;

DOI:10.5012/bkcs.2011.32.3.909

Reference yield:

3,4-bis(2-methoxyethoxy)-benzamide (1418289-91-4) → 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile (950596-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux

2.1: nitric acid / acetic acid / 4 h / 0 °C

3.1: sodium dithionite / water / 3 h / 50 °C

3.2: 0.5 h / 65 °C

With sodium dithionite; phosphorus pentoxide; nitric acid; In 5,5-dimethyl-1,3-cyclohexadiene; water; acetic acid;

DOI:10.5012/bkcs.2011.32.3.909

upstream raw materials:

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

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

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

3,4-bis(2-methoxyethoxy)-benzoic acid

Downstream raw materials:

erlotinib

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

erlotinib hydrochloride

N-(3-trimethylsilyl-ethynyl)-6,7-bis(2-methoxyethoxy)-4-quinolyl-amine

Refernces

• 1、 -. "Method for synthesizing aniline compound, catalyst and application thereof". Paragraph 0068; 0069. . Retrieved 2019/04/17.
• 2、 Chen, Li,Zhang, Yaling,Liu, Juan,Wang, Weijia,Li, Xiabing,Zhao, Lijun,Wang, Wei,Li, Baolin. "Novel 4-arylaminoquinazoline derivatives with (E)-propen-1-yl moiety as potent EGFR inhibitors with enhanced antiproliferative activities against tumor cells". . p. 689 - 697. Retrieved 2017/07/17.