NorrChemica™
Pyridin-4-ylboronic Acid
Pyridin-4-ylboronic Acid | CAS 1692-15-5 | ≥95%
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Technical Specifications
| CAS Number | 1692-15-5 |
| EC / EINECS Number | 671-679-4 |
| MDL Number | MFCD01074545 |
| SMILES | B(C1=CC=NC=C1)(O)O |
| InChI | InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H |
| InChIKey | QLULGIRFKAWHOJ-UHFFFAOYSA-N |
| PubChem CID | 2734379 |
| Molecular Formula | C₅H₆BNO₂ |
| Molecular Weight | 122.92 g/mol |
| Melting Point | >300 °C (dec.) |
| Solubility | Soluble in alcoholic solvents, acetonitrile, DMF, DMSO. |
| Purity | ≥95%. May contain varying amounts of the corresponding boronic acid anhydrides |
| Physical Form | White to pale yellow crystalline powder |
| HS Code | 2931.90 |
| Country of Origin | Finland |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store in a cool, dry place in a tightly sealed container |
Product Description & Scientific Applications
Pyridin-4-ylboronic acid (4-pyridylboronic acid; pyridine-4-boronic acid; 4-boronopyridine) is an electron-poor heteroaryl boronic acid carrying boron at the 4-position of pyridine. It resists protodeboronation and behaves as a bench-stable coupling partner, and the Lewis-basic ring nitrogen additionally serves as a metal-coordinating site. It is a building block for pharmaceuticals, N-donor ligands, and coordination polymers.
May contain small amounts of the cyclic anhydride pyridin-4-ylboroxine. Under aqueous or basic coupling conditions the two forms re-equilibrate and the impact on yield is minor.
Applications and Reactions
- Protodeboronation resistance: unlike the labile 2-pyridyl isomer, boron at the 4-position resists base-mediated protodeboronation, so the boronic acid survives coupling instead of being lost as pyridine.
- Suzuki–Miyaura coupling: with aryl and heteroaryl halides under palladium catalysis to install the 4-pyridyl group into biaryls and drug-like scaffolds.
- Coordination chemistry and ligand synthesis: the ring nitrogen is a Lewis-basic donor, and 4-pyridyl units installed by coupling act as N-donor sites and linear linkers in metal complexes, coordination polymers, and MOFs.
- Pharmaceutical building block: the 4-pyridyl group is a common pharmacophore, and the boronic acid installs it into medicinal-chemistry intermediates.
- Rhodium-catalysed conjugate addition: aryl donor in rhodium-catalysed 1,4-addition to α,β-unsaturated carbonyls, with an alcohol solvent suppressing competing protodeboronation under rhodium catalysis.
- Protected forms: available as the pinacol ester (Bpin) or MIDA boronate, or the potassium trifluoroborate, as bench-stable alternatives for demanding or orthogonal couplings.
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.
Shipping Destinations
- EU & UK: Priority delivery, 2–5 business days.
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- Worldwide: 7–14 business days, selected locations.
Safety Information
| GHS Pictograms |
|
| Signal Word | Warning |
| Hazard Class | Not regulated for transport |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H315 - H319 - H335 |
| P-Statements | P261 - P264 - P271 - P280 - P302+P352 - P304+P340 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501 |
