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Key Documents

436836

Sigma-Aldrich

2-Thienylboronic acid

≥95.0%

Sinônimo(s):

2-Thienylboric acid, 2-Thienylboronic acid, Thien-5-ylboronic acid, Thiophene-2-boronic acid

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About This Item

Fórmula empírica (Notação de Hill):
C4H5BO2S
Número CAS:
Peso molecular:
127.96
Beilstein:
112375
Número MDL:
Código UNSPSC:
12352103
ID de substância PubChem:
NACRES:
NA.22

Ensaio

≥95.0%

forma

solid

pf

138-140 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

OB(O)c1cccs1

InChI

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

chave InChI

ARYHTUPFQTUBBG-UHFFFAOYSA-N

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Aplicação

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

Outras notas

Contains varying amounts of anhydride

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


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Visite a Biblioteca de Documentos

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
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
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
Yinghui Chen et al.
The Journal of organic chemistry, 77(5), 2192-2206 (2012-02-10)
2-Thienyl and 2,6-bisthienyl BODIPY derivatives (BS-SS and BS-DS) were prepared that show intense absorption (ε = 65000 M(-1) cm(-1) at 507 nm) and a large Stokes shift (96 nm) vs the small Stokes shift of typical BODIPY (<15 nm). Control
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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