3-Bromothiophene-2-boronic acid

Base Information

• Chemical Name: 3-Bromothiophene-2-boronic acid
• CAS No.: 162607-26-3
• Molecular Formula: C₄H₄BBrO₂S
• Molecular Weight: 206.856
• DSSTox Substance ID: DTXSID10376425
• Wikidata: Q72512987
• Mol file: 162607-26-3.mol

Synonyms:3-Bromothiophene-2-boronic acid;162607-26-3;(3-bromothiophen-2-yl)boronic Acid;3-bromothiophen-2-ylboronic acid;Boronic acid,(3-bromo-2-thienyl)-(9ci);3-bromo-2-thiopheneboronic acid;BORONIC ACID, (3-BROMO-2-THIENYL)-;SCHEMBL910699;DTXSID10376425;(3-bromothiophen-2-yl)boronicAcid;MFCD01114697;AKOS002662606;AB08337;AS-39273;CS-0174366;FT-0604696;EN300-187298;A810391;J-512147

Chemical Property of 3-Bromothiophene-2-boronic acid

Chemical Property:

• Vapor Pressure: 1.34E-05mmHg at 25°C
• Melting Point: 201-203℃
• Refractive Index: 1.629
• Boiling Point: 353.2 °C at 760 mmHg
• PKA: 8.14±0.58(Predicted)
• Flash Point: 167.4 °C
• PSA: 68.70000
• Density: 1.87 g/cm³
• LogP: 0.19040
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 205.92084
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

3-Bromothiophene-2-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CS1)Br)(O)O

Technology Process of 3-Bromothiophene-2-boronic acid

There total 6 articles about 3-Bromothiophene-2-boronic 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: 89.3%

3-Bromothiophene (872-31-1) + Trimethyl borate (121-43-7,63156-11-6) + ammonium chloride (12125-02-9) → (3-bromothiophen-2-yl)boronic acid (162607-26-3)

Guidance literature:

3-Bromothiophene; With n-butyllithium; diisopropylamine; In 2-methyltetrahydrofuran; at -80 - -65 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In 2-methyltetrahydrofuran; at -80 - 20 ℃; for 1h; Inert atmosphere;

ammonium chloride; In 2-methyltetrahydrofuran; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 88.9%

3-Bromothiophene (872-31-1) + Triisopropyl borate (5419-55-6) + ammonium chloride (12125-02-9) → (3-bromothiophen-2-yl)boronic acid (162607-26-3)

Guidance literature:

3-Bromothiophene; With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 - 0 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -80 - 20 ℃; Inert atmosphere;

ammonium chloride; In tetrahydrofuran; Inert atmosphere;

Reference yield:

3-Bromothiophene (872-31-1) + Trimethyl borate (121-43-7,63156-11-6) → (3-bromothiophen-2-yl)boronic acid (162607-26-3)

Guidance literature:

3-Bromothiophene; With n-butyllithium; diisopropylamine; In tetrahydrofuran; cyclohexane; at -70 - -65 ℃; for 0.5h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -3 - 20 ℃; for 2.25h;

With hydrogenchloride; In water; regioselective reaction;

DOI:10.1021/ol3022897

upstream raw materials:

(3-bromo-2-thienyl)lithium

diethyl ether

boric acid tributyl ester

2,3-dibromothiophen

Downstream raw materials:

3-bromo-2-aminothiophene

Refernces

• 1、 -. "A 3 - bromo - 2 - amino thiophene synthetic method (by machine translation)". Paragraph 0016. . Retrieved 2018/04/26.
• 2、 Tietz, Jonathan I.,Seed, Alexander J.,Sampson, Paul. "Preparation of brominated 2-alkoxythiophenes via oxidation and etherification of 2-thienyltrifluoroborate salts". supporting information. p. 5058 - 5061. Retrieved 2013/01/15.