Description

1H-Indol-6-ylboronic acid (CAS No. 147621-18-9) is a high-purity boronic acid derivative with the molecular formula C₈H₈BNO₂, widely used in organic synthesis and pharmaceutical research. This compound features an indole scaffold coupled with a boronic acid functional group, making it a versatile building block for Suzuki-Miyaura cross-coupling reactions. Its precise molecular weight of 160.97 g/mol and well-defined structure ensure consistent performance in synthetic applications. Suitable for researchers and scientists, this product is rigorously tested for purity (typically ≥95% by HPLC or NMR) and is available in various quantities to meet laboratory-scale or industrial demands. Store in a cool, dry place under inert conditions to maintain stability.

Properties

• CAS Number: 147621-18-9
• Complexity: 165
• IUPAC Name: 1H-indol-6-ylboronic acid
• InChI: InChI=1S/C8H8BNO2/c11-9(12)7-2-1-6-3-4-10-8(6)5-7/h1-5,10-12H
• InChI Key: ZVMHOIWRCCZGPZ-UHFFFAOYSA-N
• Exact Mass: 161.0648087
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.97
• SMILES: B(C1=CC2=C(C=C1)C=CN2)(O)O
• Topological: 56.3
• Monoisotopic Mass: 161.0648087
• Synonyms: 1H-indol-6-ylboronic Acid, 627-185-6, Indole-6-boronic acid, 147621-18-9, (1H-indol-6-yl)boronic acid, 6-Indolylboronic Acid, 6-Indoleboronic acid, Indole-6-BoronicAcid, 1H-INDOLE-6-BORONIC ACID, BORONIC ACID, B-1H-INDOL-6-YL-, 6-BORONOINDOLE, 1H-INDOL-6-YL-6-BORONIC ACID, 6-indole boronic acid, MFCD03095176, 1~{H}-indol-6-ylboronic acid, CHEMBL4071778, Boronic acid, 1H-indol-6-yl-, indol-6-boronic acid, SCHEMBL6091, 1H-indol-6-yl-boronic acid, 1H-indole-6-yl-boronic acid, DTXSID10376809, BCP27170, STR09340, INDOLE-6-BORONIC ACID 98%, BDBM50266944, SBB071314, AKOS005259574, PB15735, DB-000509, CS-0007655, I0803, EN300-212520, 6-Indoleboronic Acid (contains varying amounts of Anhydride pound(c), JB8

Application

1H-Indol-6-ylboronic acid is a key intermediate in the synthesis of indole-containing pharmaceuticals, agrochemicals, and functional materials. It is particularly valuable in Suzuki-Miyaura cross-coupling reactions to construct biaryl or heteroaryl structures. Researchers also utilize it in the development of kinase inhibitors and other bioactive molecules targeting indole-based pathways. Its boronic acid group enables efficient conjugation with halides or triflates under palladium catalysis.

Safety and Hazards

GHS Hazard Statements

• H315 (94.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (98.7%): 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 (94.7%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (98.7%)

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