t-butyl 3,5-diethynylbenzoate

Base Information

• Chemical Name: t-butyl 3,5-diethynylbenzoate
• CAS No.: 791090-37-4
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.275
• Mol file: 791090-37-4.mol

Synonyms:t-butyl 3,5-diethynylbenzoate

Chemical Property of t-butyl 3,5-diethynylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl 3,5-diethynylbenzoate

There total 3 articles about t-butyl 3,5-diethynylbenzoate 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: 93.0%

t-butyl 3,5-di(trimethylsilylethynyl)benzoate (791090-36-3) → t-butyl 3,5-diethynylbenzoate (791090-37-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

DOI:10.1021/ja046531v

Reference yield:

methyl 3-bromo-5-iodobenzoate (188813-07-2) → t-butyl 3,5-diethynylbenzoate (791090-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane / 0.33 h

1.2: 98 percent / tetrahydrofuran; hexane / 18 h / 20 °C

2.1: 99 percent / Pd₂(dba)3; CuI; PPh₃ / triethylamine

3.1: 93 percent / tetrabutylammonium fluoride; glacial acetic acid / tetrahydrofuran / 0.08 h / 20 °C

With copper(l) iodide; n-butyllithium; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; triethylamine; In tetrahydrofuran; hexane; 2.1: Sonogashira's coupling;

DOI:10.1021/ja046531v

Reference yield:

3-bromo-5-iodobenzoic acid tert-butyl ester (690260-92-5) → t-butyl 3,5-diethynylbenzoate (791090-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Pd₂(dba)3; CuI; PPh₃ / triethylamine

2: 93 percent / tetrabutylammonium fluoride; glacial acetic acid / tetrahydrofuran / 0.08 h / 20 °C

With copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; triethylamine; In tetrahydrofuran; 1: Sonogashira's coupling;

DOI:10.1021/ja046531v

upstream raw materials:

t-butyl 3,5-di(trimethylsilylethynyl)benzoate

methyl 3-bromo-5-iodobenzoate

3-bromo-5-iodobenzoic acid tert-butyl ester

Downstream raw materials:

t-butyl 3,5-di(benzoylbiphenylethynyl)benzoate