4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid

Base Information

• Chemical Name: 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid
• CAS No.: 1220572-77-9
• Molecular Formula: C₁₁H₁₉BO₂SSi
• Molecular Weight: 254.233

Synonyms:4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid

Chemical Property of 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid

Chemical Property:

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Technology Process of 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid

There total 6 articles about 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid 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: 62.0%

1-[(4-bromophenyl)sulfanyl]-2-(trimethylsilyl)ethane (221292-39-3) → 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid (1220572-77-9)

Guidance literature:

1-[(4-bromophenyl)sulfanyl]-2-(trimethylsilyl)ethane; With tert.-butyl lithium; In tetrahydrofuran; pentane; for 2.33333h; Inert atmosphere; Schlenk technique;

With Triisopropyl borate; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 17h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c8cc09681c

Reference yield:

4-bromo-phenol (106-41-2) → 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid (1220572-77-9)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide / 80 °C

2: diphenylether / 259 °C

3: potassium hydroxide / methanol / 80 °C

4: 2,2'-azobis(isobutyronitrile) / 100 °C

5: n-butyllithium / tetrahydrofuran / -78 - 20 °C

6: water

With n-butyllithium; 2,2'-azobis(isobutyronitrile); water; sodium hydride; potassium hydroxide; In tetrahydrofuran; methanol; diphenylether; N,N-dimethyl-formamide; 2: Newman-Kwart rearrangement;

DOI:10.2533/chimia.2010.140

Reference yield:

S-(4-bromophenyl) dimethylcarbamothioate (7305-13-7) → 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid (1220572-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide / methanol / 80 °C

2: 2,2'-azobis(isobutyronitrile) / 100 °C

3: n-butyllithium / tetrahydrofuran / -78 - 20 °C

4: water

With n-butyllithium; 2,2'-azobis(isobutyronitrile); water; potassium hydroxide; In tetrahydrofuran; methanol;

DOI:10.2533/chimia.2010.140

upstream raw materials:

1-[(4-bromophenyl)sulfanyl]-2-(trimethylsilyl)ethane

4-bromo-phenol

S-(4-bromophenyl) dimethylcarbamothioate

O-(4-bromophenyl) N,N-dimethylcarbamothioate

Downstream raw materials:

1,4-bis{4-[2-(trimethylsilyl)ethylthio]phenyl}-2,5-bis[(E)-2-phenylethenyl]benzene

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