NorrChemica™
5-Pyrimidylboronic Acid
5-Pyrimidylboronic Acid | CAS 109299-78-7 | ≥98%
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Technical Specifications
| CAS Number | 109299-78-7 |
| EC / EINECS Number | 673-929-8 |
| MDL Number | MFCD03002366 |
| SMILES | B(C1=CN=CN=C1)(O)O |
| InChI | InChI=1S/C4H5BN2O2/c8-5(9)4-1-6-3-7-2-4/h1-3,8-9H |
| InChIKey | HZFPPBMKGYINDF-UHFFFAOYSA-N |
| PubChem CID | 2795193 |
| Molecular Formula | C₄H₅BN₂O₂ |
| Molecular Weight | 123.91 g/mol |
| Melting Point | 110–114 °C |
| Solubility | Slightly soluble in water; soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥98%. May contain varying amounts of the corresponding boronic acid anhydrides. |
| Physical Form | White to light yellow crystalline powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store at 2–8°C in a tightly sealed container. Protect from moisture and light. |
Product Description & Scientific Applications
5-Pyrimidylboronic Acid (pyrimidin-5-ylboronic acid) is a compact N-rich heteroarylboronic acid for installing the pyrimidin-5-yl unit into biaryl and heteroaryl frameworks.
May contain small amounts of the cyclic anhydride 5-pyrimidylboroxine. 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 give pyrimidin-5-yl biaryls, heterobiaryls, and styrenyl heteroarenes.
Heteroaryl–heteroaryl construction: documented in the synthesis of heteroarylpyrimidines by coupling with heteroaryl halide partners.
Protodeboronation-sensitive coupling partner: N-heteroarylboronic acids can show condition-dependent protodeboronation; masked boronate forms or milder coupling conditions may improve reliability where instability is observed.
Pyrimidin-5-yl scaffold installation: introduces a diazine ring with two ring nitrogens, useful when replacing phenyl or pyridyl units in structure–property studies.
Pharmaceutical and agrochemical intermediate: provides direct access to N-rich heteroaryl fragments for medicinal-chemistry and agrochemical intermediate libraries.
Protected boronate derivatives: precursor to pinacol, neopentyl glycol, and other boronate forms where improved handling or staged cross-coupling is preferred.
Further Reading
For boronic acids, boronic esters, 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.
- United States (DDP): 3–7 business days, duties and taxes prepaid.
- EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
- Worldwide: 7–14 business days, selected locations.
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 - H335 |
| P-Statements | P261 - P264 - P271 - P280 - P302+P352 - P304+P340 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501 |
Documentation
| Safety Data Sheet | Download PDF |
