NorrChemica™
2-Bromophenylboronic Acid
CAS 244205-40-1
≥98%
2-Bromophenylboronic Acid | CAS 244205-40-1 | ≥98%
| Pack size | Excl. VAT | Add to cart |
|---|---|---|
| 10 g−33% | ||
| 25g−43% | ||
| 50 g−44% | ||
| 100 g−40% | ||
| 250 g−23% | ||
| 500 g | €657,37€1,31/g€825,00 incl. VAT | |
| 1000 g | €1.071,71€1,07/g€1.345,00 incl. VAT |
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Technical Specifications
| CAS Number | 244205-40-1 |
| EC / EINECS Number | 678-199-4 |
| MDL Number | MFCD01114672 |
| SMILES | B(C1=CC=CC=C1Br)(O)O |
| InChI | InChI=1S/C6H6BBrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H |
| InChIKey | PLVCYMZAEQRYHJ-UHFFFAOYSA-N |
| PubChem CID | 2773294 |
| Molecular Formula | C₆H₆BBrO₂ |
| Molecular Weight | 200.83 g/mol |
| Melting Point | 109-114 °C |
| Solubility | Slightly soluble in water; soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥98%. May contain small variable amounts of boron anhydrides |
| Physical Form | White to off-white crystalline powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months under recommended storage conditions |
| Storage Conditions | Store at room temperature. Keep container tightly closed in a dry place. Mildly hygroscopic — protect from moisture |
Product Description & Scientific Applications
2-Bromophenylboronic acid (2-bromobenzeneboronic acid, o-bromophenylboronic acid) carries the boronic acid and the aryl bromide ortho to each other. This ortho relationship governs its Lewis acidity, substrate approach, chemoselectivity, and intramolecular/sequential coupling behaviour.
It may contain small amounts of the cyclic anhydride 2-bromophenylboroxine; the two forms re-equilibrate under aqueous or basic coupling conditions, with minor effect on yield.
Applications and Reactions
- Suzuki–Miyaura coupling at the boronic acid: Couples with aryl and heteroaryl electrophiles under matched Pd/phosphine/base conditions to install an ortho-bromoaryl group. Where the Ar–Br is reserved for a later intramolecular step, choose catalyst and electrophile to avoid premature oxidative addition at that bond.
- Tandem Suzuki / intramolecular arylation to fused frameworks: The retained ortho-Ar–Br serves intramolecular Pd-catalysed C–H or ring-closing arylation — giving fused-purine and phenanthridine systems (consecutive Suzuki then C–H arylation) and, by related tandem Suzuki/C–H arylation, fluoranthene-type polycyclic aromatics.
- Iterative cross-coupling with boron masking: Masking the boronic acid as its anthranilamide (AAM) boronate, which is inert under Suzuki conditions, allows coupling at the aryl bromide first; deprotection then reveals the boronic acid for the next step.
- Organocatalyst for direct amidation of carboxylic acids: A member of the Hall ortho-halogenoarylboronic acid catalyst family for direct amide formation from carboxylic acids and amines. Under room-temperature dichloromethane / 4 Å molecular sieve conditions it is active but less effective than the ortho-iodo and optimised MIBA catalysts.
- Organocatalyst for Diels–Alder reactions of α,β-unsaturated and 2-alkynoic carboxylic acids: Catalyses via reversible boronic-acid activation of the carboxyl group. Reported for acrylic-acid Diels–Alder chemistry and the most efficient catalyst screened for [4+2] cycloadditions of 2-alkynoic acids, where activation lowers the dienophile LUMO through a mixed acyl boronate intermediate.
For further reading: Boron reagent selection for Suzuki–Miyaura coupling
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- Worldwide: 7–14 business days, selected locations.
Safety Information
| GHS Pictograms |
|
| 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 |
