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
• Uses: 2-Thiopheneboronic acid can be used as reagent used for Palladium-catalyzed Suzuki-Miyaura cross-couplings; Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide ;Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer; Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters. suzuki reaction 2-Thienylboronic Acid is a reagent used for palladium-catalyzed Suzuki-Miyaura cross-couplings. It is also used in preparation of photophysical properties of oxygen-containing polycyclic aromatic triptycenes.

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:

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

2,5-di-(2-thienyl)thiazole

2-phenylthiophene

1,4-bis(2-thienyl)benzene

Refernces

• 1、 Motohashi, Hirotaka,Kato, Miki,Mikami, Koichi. "Ligand-Less Iron-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane". . p. 6483 - 6490. Retrieved 2019/05/16.
• 2、 Hinkes, Stefan P.A.,Klein, Christian D.P.. "Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids". supporting information. p. 3048 - 3052. Retrieved 2019/05/10.