5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER
• CAS No.: 676501-84-1
• Molecular Formula: C₁₀H₁₄BBrO₂S
• Molecular Weight: 289.001
• Hs Code.: 2934999090
• Mol file: 676501-84-1.mol

Synonyms:5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER;5-BroMo-2-thiopheneboronic acid pinacol ester;2-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 332.026 °C at 760 mmHg
• Flash Point: 154.604 °C
• PSA: 46.70000
• Density: 1.387 g/cm³
• LogP: 2.80980
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

98.5% ^*data from raw suppliers

1,3,2-DIOXABOROLANE,2-(5-BROMO-2-THIENYL)-4,4,5,5-TETRAMETHYL- 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER

There total 4 articles about 5-BROMOTHIOPHENE-2-BORONIC ACID PINACOL ESTER 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: 96.0%

2-bromothiophene (1003-09-4) + bis(pinacol)diborane (73183-34-3) → 2-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (676501-84-1)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 100 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b05252

Reference yield: 73.0%

2,5-dibromothiophen (3141-27-3) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (676501-84-1)

Guidance literature:

2,5-dibromothiophen; With n-butyllithium; In tetrahydrofuran; hexane; at 24 ℃; for 3.88889E-06h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at 24 ℃; for 0.000611111h;

DOI:10.1039/c2cc36197c

Reference yield: 58.0%

5-iodo-2-bromothiophene (29504-81-2) + bis(pinacol)diborane (73183-34-3) → 2-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (676501-84-1)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium acetate; In 1,4-dioxane; for 24h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c00178

upstream raw materials:

2-bromothiophene

bis(pinacol)diborane

2-thiopheneboronic acid pinacol ester

2,5-dibromothiophen

Refernces

• 1、 Pei, Xiaocong,Zhou, Guan,Li, Xuejing,Xu, Yuchen,Panicker, Resmi C.,Srinivasan, Rajavel. "Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation". supporting information. p. 5703 - 5707. Retrieved 2019/06/19.
• 2、 Nagaki, Aiichiro,Moriwaki, Yuya,Yoshida, Jun-Ichi. "Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base". supporting information. p. 11211 - 11213. Retrieved 2013/01/15.