tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate

Base Information

• Chemical Name: tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate
• CAS No.: 111291-96-4
• Molecular Formula: C16H22O2Si
• Molecular Weight: 274.435
• DSSTox Substance ID: DTXSID80553403
• Wikidata: Q82433980
• Mol file: 111291-96-4.mol

Synonyms:111291-96-4;tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate;tert-Butyl 4-((trimethylsilyl)ethynyl) benzoate;tert-butyl 4-(2-trimethylsilylethynyl)benzoate;tert-Butyl 4-[(trimethylsilyl)ethynyl]benzoate;tert-Butyl4-((trimethylsilyl)ethynyl)benzoate;tert-butyl 4-(2-(trimethylsilyl)ethynyl)benzoate;SCHEMBL9805558;DTXSID80553403;KAYVQNMVOJPPLD-UHFFFAOYSA-N;MFCD18206171;AKOS016009836;AB10916;AS-44510;CS-0088508;4-(trimethylsilylethinyl)-benzoic acid tert.-butyl ester

Chemical Property of tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate

Chemical Property:

• PSA: 26.30000
• LogP: 3.87080
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 274.138906475
• Heavy Atom Count: 19
• Complexity: 378

Purity/Quality:

97% ^*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:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CC=C(C=C1)C#C[Si](C)(C)C

Technology Process of tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate

There total 7 articles about tert-Butyl 4-((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:

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

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