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436836 Sigma-Aldrich

2-Thienylboronic acid

≥95.0%

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

  • CAS Number 6165-68-0

  • Empirical Formula (Hill Notation) C4H5BO2S

  • Molecular Weight 127.96

  •  Beilstein/REAXYS Number 112375

  •  MDL number MFCD00151850

  •  PubChem Substance ID 24867305

  •  NACRES NA.22

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Properties

Related Categories Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Boronic Acids, Organometallic Reagents More...
Quality Level   200
assay   ≥95.0%
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

Description

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

Packaging

1, 5 g in glass bottle

Other Notes

Contains varying amounts of anhydride

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Arylboronic Acids

We are pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment. Most arylboronic acids readily undergo dehydration reactions to give a cy...
ChemFiles 2001, 1.1, 5.
Keywords: Building blocks, Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers
15

References

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