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Sigma-Aldrich

2-Thienylboronic acid

≥95.0%

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Synonym(s):
2-Thienylboric acid, 2-Thienylboronic acid, Thien-5-ylboronic acid, Thiophene-2-boronic acid
Empirical Formula (Hill Notation):
C4H5BO2S
CAS Number:
Molecular Weight:
127.96
Beilstein/REAXYS Number:
112375
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0%

form

solid

mp

138-140 °C (lit.)

storage temp.

2-8°C

SMILES string

OB(O)c1cccs1

InChI

1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H

InChI key

ARYHTUPFQTUBBG-UHFFFAOYSA-N

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Related Categories

Application

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
  • Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions
  • Copper-catalyzed nitration reactions
  • Geometry relaxation-induced Large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes

Reagent used in Preparation of
  • Photophysical properties of oxygen-containing polycyclic aromatic triptycenes
  • Donor unit for donor-acceptor-type polymers via N-alkylation, Suzuki coupling, and bromination
  • Aminopyridine-based inhibitors of mitotic kinase Nek2 with potential antipoliferative effects in cancer tumors

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Man-Wah Tsang et al.
Biotechnology journal, 11(2), 257-265 (2015-08-08)
Rapid emergence of class C β-lactamases has urged an immediate need for developing class C β-lactamase specific inhibitors for effective clinical treatment. To facilitate the development of effective class C β-lactamase inhibitors, we propose a new approach for a rapid
Paolo Innocenti et al.
Journal of medicinal chemistry, 55(7), 3228-3241 (2012-03-13)
We report herein a series of Nek2 inhibitors based on an aminopyridine scaffold. These compounds have been designed by combining key elements of two previously discovered chemical series. Structure based design led to aminopyridine (R)-21, a potent and selective inhibitor
Brett VanVeller et al.
Journal of the American Chemical Society, 134(17), 7282-7285 (2012-04-19)
The cyclization and planarization of polycyclic aromatic hydrocarbons with concomitant oxygen substitution was achieved through acid catalyzed transetherification and oxygen-radical reactions. The triptycene scaffold enforces proximity of the alcohol and arene reacting partners and confers significant rigidity to the resulting
Synthesis of a novel donor unit for D-A-type polymers, 2,7-di(5-bromothiophen-2-yl)-10-hexadecyl-phenoxazine
Li, L.; et al.
Advanced Materials Research, 418-420 (2012)
Guo-Ping Lu et al.
The Journal of organic chemistry, 77(8), 3700-3703 (2012-04-07)
The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and

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