4-Ethynylbenzeneboronic acid pinacol ester, 95%

Base Information

• Chemical Name: 4-Ethynylbenzeneboronic acid pinacol ester, 95%
• CAS No.: 1034287-04-1
• Molecular Formula: C14H19BO3
• Molecular Weight: 228.099
• Hs Code.: 2934999090
• Mol file: 1034287-04-1.mol

Synonyms:4-Ethynylbenzeneboronic acid pinacol ester, 95%;2-(4-Ethynyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;4-Ethynylphenylboronic acid pinacol ester;4-Ethynylphenylboronic acid pinacol ester 95%

Chemical Property of 4-Ethynylbenzeneboronic acid pinacol ester, 95%

Chemical Property:

• Melting Point: 66-70°C
• Boiling Point: 312.2±25.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 1.96710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Insoluble in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-EthynylbenzeneboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Ethynylphenylboronic acid pinacol ester can be used:For the functionalization of platinum nanoparticles to leverage their photoluminescence properties.As an intermediate in the synthesis of covalent heterodyads of chlorophyll derivatives applicable as supramolecular light-harvesting systems.As an intermediate in the preparation of F-18 radiolabeled galectin-3 inhibitors, which are used as surrogate positron emission tomography (PET) tracers of TD139 and GB1107.

Technology Process of 4-Ethynylbenzeneboronic acid pinacol ester, 95%

There total 3 articles about 4-Ethynylbenzeneboronic acid pinacol ester, 95% 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: 66.2%

4-bromo-1-ethynylbenzene (766-96-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetylene (1034287-04-1)

Guidance literature:

4-bromo-1-ethynylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at 20 ℃; for 24h;

DOI:10.1002/pola.24772

Reference yield:

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (128376-64-7) → 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetylene (1034287-04-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 40 ℃;

DOI:10.1055/s-2007-990877

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetylene (1034287-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trans-bis(triphenylphosphine)palladium dichloride; triethylamine; triphenylphosphine / 0.5 h / 60 °C / Inert atmosphere

1.2: 16 h / Inert atmosphere; Reflux

2.1: potassium hydroxide / 1,4-dioxane / 3 h / 120 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 24 h / 20 °C

With n-butyllithium; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane;

DOI:10.1002/pola.24772

upstream raw materials:

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

4-bromo-1-ethynylbenzene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2-{4-[(E)-2-bromoethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

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

(E)-2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)but-1-en-3-yn-1-yl)isoindoline-1,3-dione

Refernces

• 1、 Lo, Chih-Nan,Hsu, Chain-Shu. "Synthesis and electroluminescence properties of white-light single polyfluorenes with high-molecular weight by click reaction". experimental part. p. 3355 - 3365. Retrieved 2012/05/04.