2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate

Base Information

• Chemical Name: 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate
• CAS No.: 862903-82-0
• Molecular Formula: C₁₄H₁₆INO₄
• Molecular Weight: 389.19
• Mol file: 862903-82-0.mol

Synonyms:2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate

Chemical Property of 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate

There total 4 articles about 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate 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: 98.0%

4-amino-3-iodo-5-trimethylsilanylethynyl-benzoic acid 2-(2-methoxy-ethoxy)-ethyl ester (862903-81-9) → 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate (862903-82-0)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ja0547984

Reference yield:

2-(2-methoxyethoxy)ethyl 4-aminobenzoate (49744-35-6) → 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate (862903-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / I₂; Ag₂SO₄ / ethanol / 1 h / 20 °C

2: 50 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 18 h / 58 - 60 °C

3: 98 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; iodine; silver sulfate; acetic acid; triethylamine; In tetrahydrofuran; ethanol; 2: Sonogashira coupling;

DOI:10.1021/ja0547984

Reference yield:

2-(2-methoxyethoxy)ethyl 4-amino-3,5-diiodobenzoate (862903-80-8) → 2-(2-methoxyethoxy)ethyl 4-amino-3-ethynyl-5-iodobenzoate (862903-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 18 h / 58 - 60 °C

2: 98 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; 1: Sonogashira coupling;

DOI:10.1021/ja0547984

upstream raw materials:

4-amino-3-iodo-5-trimethylsilanylethynyl-benzoic acid 2-(2-methoxy-ethoxy)-ethyl ester

2-(2-methoxyethoxy)ethyl 4-aminobenzoate

2-(2-methoxyethoxy)ethyl 4-amino-3,5-diiodobenzoate

p-aminoethylbenzoate

Downstream raw materials:

C₂₈H₃₀I₂N₂O₈

Refernces

• 1、 Chang, Kyoung-Jin,Kang, Byung-Nam,Lee, Min-Hee,Jeong, Kyu-Sung. "Oligoindole-based foldamers with a helical conformation induced by chloride". . p. 12214 - 12215. Retrieved 2007/10/03.