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CAS 4347-33-5

5-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride) TCI F0549

5-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride) TCI F0549

Chemical Identity

Other names
5-Formyl-2-thienylboronic Acid (contains varying amounts of Anhydride)
CAS No.
4347-33-5
PubChem
CID 2773430·SID 87558578
Formula
C5H5BO3S
Molecular weight
155.96 g/mol
Storage
0-10°C
Reference databases
ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
(5-formylthiophen-2-yl)boronic acid
SMILES
B(C1=CC=C(S1)C=O)(O)O
InChIKey
DEQOVKFWRPOPQP-UHFFFAOYSA-N
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5-Formyl-2-thiopheneboronic Acid from TCI (CAS 4347-33-5) is a thiophene-based heterocyclic compound with two key functional groups: a boronic acid group at the 2-position and an aldehyde (formyl) group at the 5-position. This combination makes it a versatile building block for modern organic synthesis. In the laboratory, its main role is as a coupling partner in palladium-catalysed cross-coupling reactions. Chemists use it to build molecular frameworks containing a thiophene ring, a structure common in organic electronic materials and in bioactive candidate compounds.

The main advantage of this material is that it is bifunctional. The boronic acid group can react selectively in Suzuki-Miyaura coupling, and the aldehyde group remains available for later transformations such as condensation, reductive amination, imine formation, or Wittig reactions. Researchers can therefore plan stepwise synthetic routes without adding extra functional groups. As the product name states, the material contains varying amounts of anhydride. This is a common property of boronic acids, which tend to form boroxines through dehydration, and it does not reduce the compound's usefulness as a coupling reagent.

In Indonesian laboratories, this compound is mostly used in university organic chemistry research groups, in pharmaceutical and medicinal chemistry research units, and in materials science laboratories working on organic semiconductors and conjugated systems. Postgraduate students and researchers use it to prepare thiophene-containing intermediates, to study new coupling methods, and to build compound libraries for screening. Because it comes from TCI, a supplier widely used in academic and industrial research, laboratories can rely on consistent product identification and documentation for their synthetic work.

TCI brochures (PDF)

  • Suzuki-Miyaura cross-coupling: the boronic acid group at the 2-position reacts selectively with aryl or heteroaryl halides under palladium catalysis to give thiophene-containing biaryl frameworks.
  • Synthesis of organic electronic materials: thiophene units are common in conjugated systems, so this reagent helps build precursors for semiconductors, dyes, and other functional organic materials.
  • Medicinal chemistry and bioactive candidates: the thiophene core and the reactive aldehyde let researchers build and then diversify heterocyclic scaffolds for exploring bioactive compounds.
  • Reductive amination and imine formation: after coupling, the formyl group at the 5-position stays available for reaction with amines, which makes it easy to add nitrogen-containing substituents.
  • Condensation and Wittig reactions: the aldehyde group allows chain extension and alkene formation, so stepwise synthetic routes can proceed without adding extra functional groups.

Brand TCI (product code F0549)
CAS number 4347-33-5
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes see the available options on the product listing
Physical form —
Storage follow the conditions on the TCI label and Safety Data Sheet
  • Composition note: contains varying amounts of anhydride (boroxine), which is typical of boronic acids

Store this compound in its original, tightly closed container in a cool, dry, well-ventilated place, away from heat sources and direct sunlight. Follow the storage conditions given on the TCI label and Safety Data Sheet. Boronic acids can dehydrate to form anhydrides, and the aldehyde group may be sensitive to air and moisture, so reseal the container promptly after each use. Handle the material in a fume hood. Wear suitable gloves, safety glasses, and a laboratory coat, and avoid inhaling dust or letting it touch skin or eyes. Dispose of waste according to local regulations and your institution's chemical waste procedures.

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