NorrChemica™
(1H-Indol-5-yl)boronic Acid
(1H-Indol-5-yl)boronic Acid | CAS 144104-59-6 | ≥97%
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Technical Specifications
| CAS Number | 144104-59-6 |
| EC / EINECS Number | 627-180-9 |
| MDL Number | MFCD01319013 |
| SMILES | B(C1=CC2=C(C=C1)NC=C2)(O)O |
| InChI | InChI=1S/C8H8BNO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10-12H |
| InChIKey | VHADYSUJZAPXOW-UHFFFAOYSA-N |
| PubChem CID | 2734361 |
| Molecular Formula | C₈H₈BNO₂ |
| Molecular Weight | 160.97 g/mol |
| Melting Point | 170–175 °C |
| Solubility | Soluble in alcoholic solvents, acetonitrile, DMF, DMSO |
| Purity | ≥97%. May contain varying amounts of the corresponding boronic acid anhydrides |
| Physical Form | White to light brown powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture. |
| Storage Conditions | Store refrigerated (2–8 °C) in a tightly sealed container, protected from light. |
Product Description & Scientific Applications
(1H-Indol-5-yl)boronic Acid is an unprotected indolylboronic acid for installing the 1H-indol-5-yl unit into aryl, heteroaryl, polycyclic, and conjugated frameworks.
May contain small amounts of the cyclic anhydride 1H-indol-5-ylboroxine. 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, and activated aryl electrophiles to give 5-arylindoles, heteroaryl-indoles, and π-extended indole products under matched Pd/base conditions.
Polycyclic scaffold synthesis: documented in Suzuki routes to aryl-hetarylfurocoumarins, aryl-substituted oxabenzindoles, and methanobenzindole frameworks.
Medicinal-chemistry intermediates: provides indole-containing fragments for MMP-inhibitor intermediates, substituted pyrimidines, tubulin-polymerisation-inhibitor intermediates, and related pharmaceutical research scaffolds.
Rhodium-catalysed conjugate addition: serves as a heteroaryl donor in 1,4-addition to unprotected maleimides, giving indolyl-substituted succinimide products.
Oxidative coupling and trifluoromethylation: participates in Pd- or Cu-mediated coupling with mercaptoacetylenes to access sulfur-containing alkynyl indole derivatives; the boronic acid or related boronate forms can also access 5-trifluoromethylindoles.
Materials and organic electronics: indole-containing building blocks are used in organic electronic materials, including hole-transport and emissive-layer architectures. 5-Functionalised indole derivatives can be incorporated into conjugated oligomers and copolymers to tune bandgap, HOMO/LUMO levels, and photophysical behaviour for photovoltaic, OLED, and fluorescence-sensor research.
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 | 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 |
