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436836

Sigma-Aldrich

2-Thienylboronic acid

≥95.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C4H5BO2S
CAS Number:
6165-68-0
Molecular Weight:
127.96
Beilstein/REAXYS Number:
112375
MDL number:
MFCD00151850
UNSPSC Code:
12352103
PubChem Substance ID:
24867305
NACRES:
NA.22

Quality Level

200

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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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
GHS07

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Chain-growth catalyst transfer polycondensation of a conjugated alternating copolymer
Ono, R. J.; Bielawski, C. W.
Polymeric Materials: Science and Engineering Preprints (2012)
Synthesis of a novel fluorene derivative for polyfluorenes. 7,7'-Di(5-bromothiophen-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene
Li, L.; et al.
Advanced Materials Research, 418-420 (2012)
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
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