Thiophene-2-boronic acid

Base Information

• Chemical Name: Thiophene-2-boronic acid
• CAS No.: 6165-68-0
• Molecular Formula: C4H5BO2S
• Molecular Weight: 127.959
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID60370059
• Nikkaji Number: J633.709K
• Wikidata: Q72508796
• ChEMBL ID: CHEMBL141272
• Mol file: 6165-68-0.mol

Synonyms:Thiophene-2-boronic acid;6165-68-0;2-Thiopheneboronic acid;thiophen-2-ylboronic acid;2-Thienylboronic acid;Thienylboronic acid;2-Thiopheneboronicacid;thiophene2-boronic acid;Boronic acid, thienyl-;MFCD00151850;2-thiophene boronic acid;thiophene 2-boronic acid;(thiophen-2-yl)boronic acid;thiophen-2-yl-2-boronic acid;CHEMBL141272;thiophen-2-ylboranediol;thiopheneboronic;thiophen-2-boronic;thiopheneboronic acid;thiophenylboronic acid;2-thiopheneboric acid;2thiopheneboronic acid;2-thiopeneboronic acid;2-thiophenboronic acid;2-thipheneboronic acid;2-thienyl boronic acid;2-thienyl-boronic acid;2-thienyl-boronic-acid;2-thiophene boric acid;thien-2-ylboronic acid;2-thiophen boronic acid;2-thiophen-boronic acid;2-thiophenylboronic acid;thiophen-2-boronic acid;thiophen-2-ylboronicacid;2-thiophene-boronic acid;2-thiophenyl boronic acid;thiophenyl 2-boronic acid;thiophen-2-yl boronic acid;thiophen-2-yl-boronic acid;SCHEMBL38298;DTXSID60370059;BCP26856;2-Thienylboronic acid, >=95.0%;AC-788;BBL104405;BDBM50067899;STK503714;AKOS000265495;AB04002;AS-3012;CS-W000053;NCGC00249453-01;AM804138;SY002974;A8542;FT-0601795;T1772;EN300-49146;Thiophen-2-ylboronic acid;J-400313;F9995-0586;Z330828022;InChI=1/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7

Chemical Property of Thiophene-2-boronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00112mmHg at 25°C
• Melting Point: 138-140 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 287.917 °C at 760 mmHg
• PKA: 8.41±0.53(Predicted)
• Flash Point: 127.928 °C
• PSA: 68.70000
• Density: 1.321 g/cm³
• LogP: -0.57210
• Storage Temp.: 0-6°C
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 128.0103307
• Heavy Atom Count: 8
• Complexity: 78.4

Purity/Quality:

99% ^*data from raw suppliers

2-Thienylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CS1)(O)O
• General Description: 2-Thiopheneboronic acid (also known as 2-thienylboronic acid) serves as an efficient catalyst in the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones (DHPMs), demonstrating high catalytic activity with yields up to 97%. This method improves upon the traditional Biginelli reaction by addressing limitations such as prolonged reaction times and low yields, while enabling the production of DHPMs with notable pharmacological properties, including anti-inflammatory, antitumor, and antibacterial activities.

Technology Process of Thiophene-2-boronic acid

There total 28 articles about Thiophene-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: 99.0%

2-Iodothiophene (3437-95-4,149762-92-5) → thiophene boronic acid (6165-68-0)

Guidance literature:

2-Iodothiophene; With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride; In tetrahydrofuran; at 65 ℃; for 12h; Inert atmosphere;

With methanol; In tetrahydrofuran; at 0 ℃; Further stages; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.065

Reference yield: 99.0%

2-thiopheneboronic acid MIDA ester (1158984-92-9) → thiophene boronic acid (6165-68-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 23 ℃; for 0.333333h;

Reference yield: 96.0%

dihydroxy-methyl-borane (13061-96-6) + 2-thiopheneboronic acid pinacol ester (193978-23-3) → thiophene boronic acid (6165-68-0)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

upstream raw materials:

2-thienyl lithium

diethyl ether

boric acid tributyl ester

2-bromothiophene

Downstream raw materials:

(5-bromothiophene-2-yl)boronic acid

2,6-bis(thiophen-2-yl)pyridine

2,2':5',2''-terthiophene

2,5-dimethyl-3,4-di-(2-thienyl)thiophene

Refernces

An efficient one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalysed by 2-thienylboronic acid

10.3184/174751912X13318375421203

The research presents an efficient one-pot synthesis method for 3,4-dihydropyrimidin-2-(1H)-ones/thiones (DHPMs), a class of compounds with significant therapeutic and pharmacological properties such as anti-inflammatory, antitumor, and antibacterial activities. The study aimed to improve upon the traditional Biginelli reaction, which often suffers from long reaction times and low product yields. The researchers utilized 2-thienylboronic acid as a novel catalyst, achieving good to excellent yields, with some reaching up to 97%.