tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate

Base Information

• Chemical Name: tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate
• CAS No.: 111291-96-4
• Molecular Formula: C16H22O2Si
• Molecular Weight: 274.435
• Mol file: 111291-96-4.mol

Synonyms:

Chemical Property of tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate

Chemical Property:

• PSA: 26.30000
• LogP: 3.87080
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate

There total 7 articles about tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate 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: 99.0%

tert-butyl 4-iodobenzoate (120363-13-5) + trimethylsilylacetylene (1066-54-2) → tert-butyl 4-<(trimethylsilyl)ethynyl>benzoate (111291-96-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; for 18h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.9b02544

Reference yield: 59.0%

trimethylsilylacetylene (1066-54-2) → tert-butyl 4-<(trimethylsilyl)ethynyl>benzoate (111291-96-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201800595

Reference yield:

tert-butyl-4-bromobenzoate (59247-47-1) + trimethylsilylacetylene (1066-54-2) → tert-butyl 4-<(trimethylsilyl)ethynyl>benzoate (111291-96-4)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; at 100 ℃; for 16h;

DOI:10.1021/jo00276a023

upstream raw materials:

tert-butyl-4-bromobenzoate

trimethylsilylacetylene

4-chlorobenzoyl chloride

tert-butyl 4-iodobenzoate

Downstream raw materials:

4-ethynylbenzoic acid tert-butyl ester

diethyl N-<4-<<2-(pivaloylamino)-4-hydroxypyrido<2,3-d>pyrimidin-6-yl>ethynyl>benzoyl>-L-glutamate

2-(pivaloylamino)-4-hydroxy-6-<<4-(tert-butoxycarbonyl)phenyl>ethynyl>pyrido<2,3-d>pyrimidine

2-(pivaloylamino)-4-hydroxy-6-<(carboxyphenyl)ethynyl>pyrido<2,3-d>pyrimidine

Refernces

• 1、 Rice, Anthony T.,Martin, Maxwell I.,Warndorf, Molly C.,Yap, Glenn P. A.,Rosenthal, Joel. "Synthesis, Spectroscopic, and 1O2Sensitization Characteristics of Extended Pd(II) 10,10-Dimethylbiladiene Complexes Bearing Alkynyl-Aryl Appendages". . p. 11154 - 11163. Retrieved 2021.
• 2、 Chiu, Hsin-Chun,Tonks, Ian A.. "Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis". supporting information. p. 6090 - 6094. Retrieved 2018/05/30.