Description

5-Indolylboronic acid (CAS: 144104-59-6) is a high-purity boronic acid derivative widely utilized in pharmaceutical research, organic synthesis, and materials science. With the molecular formula C₈H₈BNO₂, this compound serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling the efficient construction of complex indole-containing scaffolds. Its exceptional reactivity and stability make it indispensable for medicinal chemistry applications, particularly in drug discovery and development.

This product is rigorously tested for quality, ensuring ≥95% purity (HPLC) with minimal impurities. Supplied as a white to off-white crystalline powder, it is packaged under inert conditions to maintain stability. Ideal for researchers and industrial scientists, 5-Indolylboronic acid is compatible with a wide range of solvents, including DMF, DMSO, and THF, facilitating seamless integration into diverse synthetic protocols.

Applications extend to the synthesis of bioactive molecules, agrochemicals, and advanced materials. Store in a cool, dry place (<20°C) under nitrogen or argon to prolong shelf life. Available in quantities ranging from milligrams to kilograms, tailored to meet both lab-scale and bulk production needs.

Properties

• CAS Number: 144104-59-6
• Complexity: 165
• IUPAC Name: 1H-indol-5-ylboronic acid
• InChI: InChI=1S/C8H8BNO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10-12H
• InChI Key: VHADYSUJZAPXOW-UHFFFAOYSA-N
• Exact Mass: 161.0648087
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.97
• SMILES: B(C1=CC2=C(C=C1)NC=C2)(O)O
• Topological: 56.3
• Monoisotopic Mass: 161.0648087
• Synonyms: 5-Indolylboronic acid, 627-180-9, 144104-59-6, Indole-5-boronic acid, (1H-indol-5-yl)boronic acid, 1H-indol-5-ylboronic Acid, 1h-indole-5-boronic acid, 5-indolyl boronic acid, 5-indolboronic acid, BORONIC ACID, B-1H-INDOL-5-YL-, MFCD01319013, 5-1H-indole boronic acid, CHEMBL342460, 1~{H}-indol-5-ylboronic acid, 1H-INDOL-5-YL-5-BORONIC ACID, Boronic acid, 1H-indol-5-yl-, 5-Indoleboronic acid, indol-5-boronic acid, indole 5-boronic acid, indole-5 boronic acid, 5-Indole boronic acid, 5-indolyl-boronic acid, indol-5-ylboronic acid, SCHEMBL5940, (1H-indol-5-yl)boronicacid, 1H-indol-5-yl boronic acid, 1H-indol-5-yl-boronic acid, DTXSID60370251, BCP00079, BBL100901, BDBM50067908, STL554695, AKOS002670086, CS-W020721, PB26056, PS-9518, SB10006, NCGC00249466-01, SY013664, DB-009559, 5-Indoleboronic acid, Indole-5-boronic acid, EN300-212500, Z1255403238, JDN

5-Indolylboronic acid is primarily employed in Suzuki-Miyaura cross-coupling reactions to synthesize indole-based pharmaceuticals and functional materials. It serves as a key intermediate in the development of kinase inhibitors, anticancer agents, and CNS-targeting drugs. Researchers also leverage its boronic acid moiety for bioconjugation and sensor development. Compatible with automated synthesis platforms, it accelerates high-throughput screening and combinatorial chemistry workflows.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.