NorrChemica™
(3-Hydroxyphenyl)boronic Acid
(3-Hydroxyphenyl)boronic Acid | CAS 87199-18-6 | ≥98%
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Technical Specifications
| CAS Number | 87199-18-6 |
| EC / EINECS Number | 677-211-5 |
| MDL Number | MFCD01074603 |
| SMILES | B(C1=CC(=CC=C1)O)(O)O |
| InChI | InChI=1S/C6H7BO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8-10H |
| InChIKey | WFWQWTPAPNEOFE-UHFFFAOYSA-N |
| PubChem CID | 2734359 |
| Molecular Formula | C₆H₇BO₃ |
| Molecular Weight | 137.93 g/mol |
| Melting Point | 210–213 °C |
| Solubility | Soluble in alcoholic solvents, acetonitrile, DMF, DMSO. |
| Purity | ≥98%. May contain varying amounts of the corresponding boronic acid anhydrides |
| Physical Form | White to off-white 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
(3-Hydroxyphenyl)boronic acid (3-boronophenol; m-hydroxyphenylboronic acid) is a bifunctional arylboronic acid carrying a phenolic hydroxyl at the 3-position. The phenol is a handle for O-functionalisation, a hydrogen-bond donor, and a metal-coordinating site; the boronic acid couples under Suzuki–Miyaura conditions and binds cis-diols and saccharides. The two orthogonal handles make it a building block for saccharide sensors, functional materials, and medicinal-chemistry intermediates.
May contain small amounts of the cyclic anhydride 3-hydroxyphenylboroxine. Under aqueous or basic coupling conditions the two forms re-equilibrate and the impact on yield is minor.
Applications and Reactions
- Saccharide and diol recognition: the boronic acid forms cyclic boronate esters with cis-diols, catechols, and sugars such as fructose and glucose, the basis of boronic-acid saccharide sensing.
- Fluorescent sensor building block: hydrothermal carbonisation gives boronic-acid-functional carbon dots for selective fructose sensing by fluorescence quenching.
- Suzuki–Miyaura coupling: with aryl and heteroaryl halides under palladium catalysis to install the 3-hydroxyphenyl group, the free phenol retained.
- Phenol functionalisation: the phenolic hydroxyl is a handle for O-alkylation and acylation, a hydrogen-bond donor, and a site for metal coordination.
- Oxidative ipso-hydroxylation: oxidation of the C–B bond gives benzene-1,3-diol (resorcinol).
- Protected building block: the boron is masked as pinacol (Bpin) or MIDA boronates and the phenol as an ether or carbonate, for orthogonal multi-step coupling.
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.
- 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 | 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 |
