4-ETHYNYLPYRIDINE

Base Information

• Chemical Name: 4-ETHYNYLPYRIDINE
• CAS No.: 630127-51-4
• Molecular Formula: C11H15BO2Si
• Molecular Weight: 218.135
• Hs Code.: 2931900090
• Mol file: 630127-51-4.mol

Synonyms:[4-(2-trimethylsilylethynyl)phenyl]boronic acid;

Chemical Property of 4-ETHYNYLPYRIDINE

Chemical Property:

• Boiling Point: 311.5±48.0 °C(Predicted)
• PKA: 8?+-.0.17(Predicted)
• PSA: 40.46000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 0.59530
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(4-[(Trimethylsilyl)ethynyl]phenyl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-ETHYNYLPYRIDINE

There total 8 articles about 4-ETHYNYLPYRIDINE 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%

trimethylsilylacetylene (1066-54-2) + 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (183677-71-6) → 2,2-dimethylpropane-1,3-diyl [4-(trimethylsilylethynyl)phenyl] boronate (183677-72-7) + 4-[(trimethylsilyl)ethynyl]phenyl boronic acid (630127-51-4)

Guidance literature:

With copper(l) iodide; diethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 120 ℃; for 0.416667h; microwave irradiation;

DOI:10.1016/j.tetlet.2006.02.012

Reference yield: 70.0%

4-iodophenylboronic acid (5122-99-6) + trimethylsilylacetylene (1066-54-2) → 4-[(trimethylsilyl)ethynyl]phenyl boronic acid (630127-51-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jacs.6b03383

Reference yield: 70.0%

Trimethyl borate (121-43-7,63156-11-6) + (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2) → 4-[(trimethylsilyl)ethynyl]phenyl boronic acid (630127-51-4)

Guidance literature:

(4-bromophenyl)(trimethylsilyl)acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 13h;

DOI:10.1039/d0dt04038j

upstream raw materials:

1-iodo-4-(trimethylsilylethynyl)benzene

trimethylsilylacetylene

2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

4-Bromophenylboronic acid

Downstream raw materials:

((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)trimethylsilane

tert-butyl (2S,4S)-4-methyl-2-[4-[4-(2-trimethylsilylethynyl)phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

methyl N-[(1S)-1-[(2S,4S)-2-[4-[4-[2-[2-[(2S,4S)-1-[(2S)-2-[methoxycarbonyl-(methyl)amino]-3-methyl-butanoyl]-4-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]ethynyl]phenyl]-1H-imidazol-2-yl]-4-methyl-pyrrolidine-1-carbonyl]-2-methyl-propyl]-N-methyl-carbamate

Refernces

• 1、 Olavarria-Contreras, Ignacio José,Perrin, Mickael L.,Chen, Zhi,Klyatskaya, Svetlana,Ruben, Mario,Van Der Zant, Herre S. J.. "C-Au Covalently Bonded Molecular Junctions Using Nonprotected Alkynyl Anchoring Groups". supporting information. p. 8465 - 8469. Retrieved 2016/07/26.
• 2、 -. "Processes for preparing of glucopyranosyl-substituted (ethynyl-benzyl)-benzene derivatives and intermediates thereof". Page/Page column 28. . Retrieved 2010/11/26.