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Sigma-Aldrich

2,5-Thiophenediylbisboronic acid

≥95.0%

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Synonym(s):
2,5-Thiophenediboronic acid
Empirical Formula (Hill Notation):
C4H6B2O4S
CAS Number:
Molecular Weight:
171.78
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95.0%

mp

250 °C (dec.) (lit.)

SMILES string

OB(O)c1ccc(s1)B(O)O

InChI

1S/C4H6B2O4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2,7-10H

InChI key

SKFDVFMUXZWWOW-UHFFFAOYSA-N

Application

2,5-Thiophenediylbisboronic acid can be used:
  • As a reactant in the metal catalyzed Suzuki cross coupling reactions.
  • To prepare 2,5-bis(2-pyridyl)thiophene, a thiophene based ligand which is used in the design of fluorescent mercury-sensor.
  • To fabricate graphene-based biosensors for the detection of glucose and Escherichia coli in a complex medium.

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Thiophene-based fluorescent mercury-sensors
Shigemoto AK, et al.
Journal of Coordination Chemistry, 69(11-13), 2081-2089 (2016)
Synthesis of 2H-benzotriazole based donor-acceptor polymers bearing carbazole derivative as pendant groups: Optical, electronical and photovoltaic properties
Jessop IA, et al.
International Journal of Electrochemical Science, 11, 9822-9838 (2016)
Construction and Evaluation of a Self-Calibrating Multiresponse and Multifunctional Graphene Biosensor
Beyranvand S, et al.
Langmuir, 35(32), 10461-10474 (2019)

Articles

The Suzuki-Miyaura cross-coupling reaction is an important and extensively used reaction in organic chemistry with applications in polymer science and in the fine chemicals and pharmaceutical industries.

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