TCI
5-Chloro-2-thiopheneboronic Acid (contains varying amounts of Anhydride) TCI C2066
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Description
TCI C2066 is 5-Chloro-2-thiopheneboronic Acid containing varying amounts of anhydride (boroxine), a heteroaromatic organoboron reagent developed specifically for carbon–carbon bond formation. In modern synthetic laboratories, boronic compounds of this type serve as the principal nucleophilic partner in Suzuki-Miyaura cross-coupling reactions, allowing a chlorine-substituted thiophene ring to be joined to a wide range of aryl and heteroaryl halides. This capability makes the reagent an important tool for researchers constructing conjugated molecules for organic electronics as well as pharmaceutical scaffolds that incorporate thiophene units.
The most notable property of this material is the reactivity of the boronic acid group at position 2 of the thiophene ring, combined with the chlorine atom at position 5 that survives the coupling step and remains available for subsequent functionalisation. It should be understood that boronic acids naturally undergo partial dehydration to form the cyclic trimeric anhydride; for that reason the product label honestly states the presence of a varying anhydride content. This does not diminish its usefulness in coupling reactions, although researchers should allow for a slight excess of reagent when calculating stoichiometry.
In Indonesian laboratories, this reagent is typically used by university research groups, pharmaceutical chemistry teams, and materials science laboratories that carry out palladium-catalysed cross-coupling work. It is commonly drawn on during postgraduate synthesis projects, in the preparation of thiophene-containing intermediates, and in the development of conjugated materials, where a reliably supplied heteroaromatic boronic acid removes the need for in-house preparation of the building block.
Laboratory Applications
- Suzuki-Miyaura cross-coupling — the boronic acid at position 2 acts as the nucleophilic partner with aryl and heteroaryl halides under palladium catalysis, forming carbon–carbon bonds reliably.
- Organic electronic materials synthesis — thiophene units are central to conjugated systems, so this reagent lets researchers install a chlorothiophene fragment into extended pi-conjugated backbones.
- Pharmaceutical scaffold construction — many drug candidates contain thiophene rings, and this building block introduces that motif directly into medicinal chemistry intermediates during discovery work.
- Sequential functionalisation strategies — the chlorine at position 5 is retained through coupling, so it can be activated later for a second, independent bond-forming step.
- Heteroaromatic building-block library preparation — synthetic groups use this reagent to generate families of substituted thiophene derivatives for structure-activity screening and subsequent methodology studies.
Specifications
- Brand: TCI
- CAS number: 162607-18-3
- Chemical name: 5-Chloro-2-thiopheneboronic Acid (contains varying amounts of Anhydride)
- Category: Chemistry > Organometallic Reagents > Organoboron [Organometallic Reagents]
- Pack sizes: available in the catalogue pack sizes offered by TCI for this item
- Storage note: keep tightly closed in a cool, dry place away from moisture
Handling and Storage
Store the reagent in its original tightly closed container in a cool, dry area, protected from moisture and direct sunlight, since boronic acids readily undergo further dehydration to the anhydride form when exposed to humid air. Amber glass or the supplier's original packaging is suitable, and containers should be resealed promptly after each use. Weighing is best carried out quickly, or under an inert atmosphere where available. Handle in a fume hood using gloves, safety goggles, and a laboratory coat, avoid inhalation of dust, and keep the material separate from strong oxidising agents. Always consult the manufacturer's safety data sheet before use.
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