NorrChemica™
4-Biphenylboronic Acid
4-Biphenylboronic Acid | CAS 5122-94-1 | ≥98%
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Technical Specifications
| CAS Number | 5122-94-1 |
| EC / EINECS Number | 675-084-0 |
| MDL Number | MFCD00093311 |
| SMILES | B(C1=CC=C(C=C1)C2=CC=CC=C2)(O)O |
| InChI | InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H |
| InChIKey | XPEIJWZLPWNNOK-UHFFFAOYSA-N |
| PubChem CID | 151253 |
| Molecular Formula | C₁₂H₁₁BO₂ |
| Molecular Weight | 198.03 g/mol |
| Melting Point | 232-245 °C |
| Solubility | Slightly soluble in water; soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥98% |
| Physical Form | White to off-white crystalline powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store at room temperature. Protect from moisture. May contain varying amounts of boroxine anhydride |
Product Description & Scientific Applications
4-Biphenylboronic Acid ([1,1′-biphenyl]-4-ylboronic acid) is a π-extended arylboronic acid for installing a rigid 4-biphenyl unit.
May contain small amounts of the cyclic anhydride 4-biphenylboroxine. 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 p-terphenyl, heteroaryl-biphenyl, styrenyl-biphenyl, and higher oligoaryl products.
Liquid-crystal intermediates: provides a rigid linear biphenyl fragment for terphenyl-type mesogenic cores and rod-shaped aromatic materials.
Conjugated materials building block: introduces biphenyl segments into π-conjugated oligomers, chromophores, and organic semiconductor intermediates.
Thiophene–phenylene hybrid scaffolds: with aryl-halide partners gives thienyl-substituted terphenyl and quinquephenyl frameworks for extended heteroaryl–phenylene systems.
Luminol–peroxidase chemiluminescence enhancement: acts as an enhancer in luminol–hydrogen peroxide–horseradish peroxidase systems, including capillary-electrophoresis chemiluminescence detection.
Boronate–diol recognition: forms reversible boronate complexes with the diol groups of mono- and disaccharides, used to estimate apparent stability constants in capillary-electrophoresis molecular-recognition studies.
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 | H302 - H315 - H319 - H335 |
| P-Statements | P261 - P264 - P270 - P271 - P280 - P301+P312 - P302+P352 - P304+P340 - P305+P351+P338 - P330 - P332+P313 - P337+P313 - P362+P364 - P501 |
Documentation
| Safety Data Sheet | Download PDF |
