2-Thienylboronic acid
2-Thienylboronic acid (CAS: 6165-68-0, C4H5BO2S) is a key organoboron compound with a molecular weight of 127.96 g/mol. Utilised primarily as a reagent in palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura, it enables the synthesis of complex organic molecules. Its applications extend to various organic transformations including alkylation, boration, and halogenation, making it a versatile building block in chemical research and development.
- IUPAC
- 2-Thienylboric acid,2-Thienylboronic acid,Thien-5-ylboronic acid,Thiophene-2-boronic acid
- Synonyms
- 2-Thienylboric acid2-Thienylboronic acidThien-5-ylboronic acidThiophene-2-boronic acid
Suzuki-Miyaura Cross-Coupling Reactions
This reagent is extensively employed in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds. It is also effective in ligand-free Suzuki couplings.
Organic Synthesis Reagent
2-Thienylboronic acid serves as a versatile building block in diverse organic synthesis pathways. It participates in alkylation, boration, coupling reactions, and halogenation processes.
Polymer Synthesis
It acts as a chain-growth catalyst transfer agent in the polycondensation of conjugated alternating copolymers. This is crucial for developing advanced polymer materials.
Fluorescent Probes and Materials
This boronic acid derivative is utilised in the preparation of materials with specific photophysical properties, such as red-emitting borondipyrromethenes (BODIPY), finding applications in fluorescent thiol probes.
| Molecular weight | 127.96 |
|---|---|
| Empirical formula | C4H5BO2S |
| Assay | ≥95.0% |
| Storage temperature | 2-8°C |
| Application | Reagent used for• Palladium-catalyzed Suzuki-Miyaura cross-couplings1 • Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide2 • Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer3 • Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters4 • Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions5 • Copper-catalyzed nitration reactions6 • Geometry relaxation-induced Large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes7 Reagent used in Preparation of• Photophysical properties of oxygen-containing polycyclic aromatic triptycenes8 • Donor unit for donor-acceptor-type polymers via N-alkylation, |
| Melting point | 138-140 °C(lit.) |
Hazard statements
- H302Harmful if swallowed
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22-36/37/38 |
| Safety statements (S) | 26-36/37 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 2-Thienylboronic acid used for?
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2-Thienylboronic acid is primarily used as a reagent in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and other organic synthesis transformations like alkylation, boration, and halogenation.
What are the CAS number and molecular formula for 2-Thienylboronic acid?
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The CAS number for 2-Thienylboronic acid is 6165-68-0, and its molecular formula is C4H5BO2S.
What grade and purity does Tech Serve Solutions supply for 2-Thienylboronic acid?
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Tech Serve Solutions supplies 2-Thienylboronic acid with an assay of ≥95.0%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.
What are the safety and handling precautions for 2-Thienylboronic acid?
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2-Thienylboronic acid is classified with a GHS07 symbol and a Warning signal word, with hazard statements including H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Recommended personal protective equipment includes a dust mask (type N95 US), eyeshields, and gloves. Handle in a well-ventilated area and avoid dust formation.
Is 2-Thienylboronic acid a controlled substance?
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The provided data does not indicate that 2-Thienylboronic acid is a controlled substance.
How is 2-Thienylboronic acid packed, shipped, and exported?
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Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals. Specific packing and shipping details will be provided upon request and in accordance with international shipping regulations.
How can I request a sample or quote for 2-Thienylboronic acid?
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Please contact our sales team directly through our website or by phone to request a sample or a quotation for 2-Thienylboronic acid.
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