Description

1H-Indole-4-boronic acid, pinacol ester (CAS No. 388116-27-6) is a high-purity boronic ester derivative of indole, designed for advanced research and synthetic applications. With the molecular formula C₁₄H₁₈BNO₂, this compound features a stable pinacol boronate group, making it an essential building block for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its IUPAC name, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, reflects its precise chemical structure, ensuring reproducibility in synthetic workflows. Ideal for pharmaceutical, agrochemical, and materials science research, this reagent is rigorously tested for quality, offering excellent solubility in common organic solvents like THF, DMF, and DMSO. Packaged under inert conditions to guarantee stability, it is a must-have for researchers seeking reliable and efficient boronic acid derivatives.

Properties

• CAS Number: 388116-27-6
• Complexity: 316
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• InChI: InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-6-5-7-12-10(11)8-9-16-12/h5-9,16H,1-4H3
• InChI Key: QDCIXBBEUHMLDN-UHFFFAOYSA-N
• Exact Mass: 243.1430590
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.11
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C3C=CNC3=CC=C2
• Topological: 34.3
• Monoisotopic Mass: 243.1430590
• Synonyms: 1H-Indole-4-boronic acid, pinacol ester, 695-961-1, 388116-27-6, Indole-4-boronic acid pinacol ester, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, Indole-4-boronic acid, pinacol ester, 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, MFCD08689896, 4-(4,4,5,5-tetramethyl(1,3,2]dioxaborolan-2-yl)-1H-indole, 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole, 1H-INDOLE, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, (1H-INDOL-4-YL)BORONIC ACID PINACOL ESTER, SCHEMBL476853, DTXSID20462343, QDCIXBBEUHMLDN-UHFFFAOYSA-N, 4-indole boronic acid pinacol ester, BBL103533, RB2036, SBB052589, STL557343, AKOS000283818, CS-W019752, PB34318, SY012840, Indole-4-boronic acid pinacol ester, 95%, DB-009193, EN300-6480642, Z2037316489, 2-indol-4-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)1H-indole, 4-(4,4,5,5tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole, 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 1H-indol-4-ylboronate, 4-(4,4,5 ,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, 4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane-2-yl)-1H-indole, 4-(4,4,5,5-tetra-methyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) 1H-indole, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, 4-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole

Application

1H-Indole-4-boronic acid, pinacol ester is widely used in palladium-catalyzed cross-coupling reactions, enabling the synthesis of complex indole-containing scaffolds for drug discovery and materials science. Its stability and reactivity make it a preferred choice for constructing biaryl and heteroaryl systems in medicinal chemistry. Researchers also employ it in the development of fluorescent probes and organic electronic materials due to its versatile indole core.

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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