NorrChemica™
(5-Bromothiophen-2-yl)boronic Acid
(5-Bromothiophen-2-yl)boronic Acid | CAS 162607-17-2 | ≥96%
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Technical Specifications
| CAS Number | 162607-17-2 |
| EC / EINECS Number | 678-207-6 |
| MDL Number | MFCD02094028 |
| SMILES | B(C1=CC=C(S1)Br)(O)O |
| InChI | InChI=1S/C4H4BBrO2S/c6-4-2-1-3(9-4)5(7)8/h1-2,7-8H |
| InChIKey | USJPOBDLWVCPGG-UHFFFAOYSA-N |
| PubChem CID | 2734319 |
| Molecular Formula | C₄H₄BBrO₂S |
| Molecular Weight | 206.85 g/mol |
| Melting Point | 95–100 °C |
| Solubility | Soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥96% |
| Physical Form | White to off-white crystalline powder |
| HS Code | 2931.90 |
| Shelf Life | 36 months under recommended storage conditions |
| Storage Conditions | Store at –20°C in a tightly sealed container. Protect from moisture and light. May contain varying amounts of boroxine anhydride |
Product Description & Scientific Applications
(5-Bromothiophen-2-yl)boronic Acid is a bifunctional heteroarylboronic acid combining a thiophen-2-ylboronic acid coupling handle with a retained 5-bromo substituent.
May contain small amounts of the cyclic anhydride 5-bromothiophen-2-ylboroxine. Under aqueous or basic coupling conditions the two forms re-equilibrate and the impact on yield is minor.
Applications and Reactions
Suzuki–Miyaura cross-coupling: couples with aryl, heteroaryl, or alkenyl electrophiles to install a 5-bromothiophen-2-yl unit in biaryl, heterobiaryl, and π-extended products.
Bifunctional C–B/C–Br handle: the boronic acid and aryl bromide can be addressed sequentially under matched conditions to access unsymmetrical 2,5-disubstituted thiophenes.
Second-site diversification: after initial Suzuki coupling, the retained C5 bromide can support further Suzuki, Sonogashira, Buchwald–Hartwig, or carbonylative transformations.
Ratanhine intermediate: documented Suzuki–Miyaura coupling partner in the synthesis of ratanhine-type acetylenic thiophene natural-product frameworks.
Organic sensitizer and BODIPY hybrids: used in Suzuki coupling routes to benzotriazole-containing dye-sensitised solar-cell sensitizers and meso-polyarylamide–BODIPY hybrid materials.
Ethynylarylboronate synthesis: the C5 bromide participates in microwave-assisted Sonogashira chemistry to give ethynyl-substituted arylboronate intermediates for further coupling or conjugation.
Further Reading
For boronic acids, boronic esters, organotrifluoroborates, protodeboronation, boroxine content, and Suzuki–Miyaura reagent selection, see NorrChemica's Lab Journal guide: Choosing Your Boron Source for Suzuki–Miyaura Coupling.
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Safety Information
| GHS Pictograms |
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| Signal Word | Warning |
| Hazard Class | None — not subject to transport regulations |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H315 - H319 |
| P-Statements | P264 - P280 - P302+P352 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501 |
Documentation
| Safety Data Sheet | Download PDF |
