2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Base Information

• Chemical Name: 2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• CAS No.: 1190376-24-9
• Molecular Formula: C₂₁H₂₃BO₃
• Molecular Weight: 334.223
• Hs Code.: 2931900090
• Mol file: 1190376-24-9.mol

Synonyms:2-{4-[(4-methoxyphenyl)ethynyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

2-[4-(4-Methoxy-phenylethynyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

There total 4 articles about 2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 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: 72.0%

4-methoxyphenylacetylen (768-60-5) + 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73852-88-7) → 2-{4-[(4-methoxyphenyl)ethynyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1190376-24-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 40 ℃; for 3h; Inert atmosphere;

DOI:10.3762/bjoc.5.11

Reference yield: 69.0%

1-bromo-4-[2-(4-methoxyphenyl)ethynyl]benzene (189099-57-8) + bis(pinacol)diborane (73183-34-3) → 2-{4-[(4-methoxyphenyl)ethynyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1190376-24-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In 1,4-dioxane; at 90 ℃;

DOI:10.1039/c5ra08989a

Reference yield:

4-methoxyphenylacetylen (768-60-5) → 2-{4-[(4-methoxyphenyl)ethynyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1190376-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 50 °C

2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 90 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; 1,4-dioxane; 2: |Suzuki Coupling;

DOI:10.1039/c5ra08989a

upstream raw materials:

4-methoxyphenylacetylen

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1,4-bromoiodobenzene

1-bromo-4-[2-(4-methoxyphenyl)ethynyl]benzene

Downstream raw materials:

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

2-[4-[2-(4-methoxyphenyl)ethyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[(η4-C4(C6H4-4-B(OCMe2)2)2(C6H4-4-OMe)2)Co(η5-C5H5)]

[(η4-C4(C6H4-4-B(OCMe2)2)2(C6H4-4-OMe)2)Co(η5-C5H5)]