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Atomfair 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole C14H18BNO2 CAS 269410-24-4

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 269410-24-4) is a high-purity boron-containing heterocyclic compound with the molecular formula C14H18BNO2. This advanced synthetic intermediate features a stable pinacol boronate ester group coupled to an indole scaffold, making it an invaluable reagent for Suzuki-Miyaura cross-coupling reactions in pharmaceutical research and materials science. The compound’s crystalline solid form (typically white to off-white) offers excellent handling stability under inert atmospheres. With >95% purity by HPLC, it is ideal for metal-catalyzed C-C bond formation , particularly in constructing complex biaryl systems for drug discovery. Proper storage at 2-8°C under nitrogen is recommended to maintain reactivity.

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Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 269410-24-4) is a high-purity boron-containing heterocyclic compound with the molecular formula C14H18BNO2. This advanced synthetic intermediate features a stable pinacol boronate ester group coupled to an indole scaffold, making it an invaluable reagent for Suzuki-Miyaura cross-coupling reactions in pharmaceutical research and materials science. The compound’s crystalline solid form (typically white to off-white) offers excellent handling stability under inert atmospheres. With >95% purity by HPLC, it is ideal for metal-catalyzed C-C bond formation, particularly in constructing complex biaryl systems for drug discovery. Proper storage at 2-8°C under nitrogen is recommended to maintain reactivity.

Properties

  • CAS Number: 269410-24-4
  • Complexity: 316
  • IUPAC Name: 5-(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)11-5-6-12-10(9-11)7-8-16-12/h5-9,16H,1-4H3
  • InChI Key: FATPQDPUKVVCLT-UHFFFAOYSA-N
  • Exact Mass: 243.1430590
  • Molecular Formula: C14H18BNO2
  • Molecular Weight: 243.11
  • SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)NC=C3
  • Topological: 34.3
  • Monoisotopic Mass: 243.1430590
  • Synonyms: 269410-24-4, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, DTXSID40370496, DTXCID10321531, 625-804-4, 5-Indoleboronic acid pinacol ester, Indole-5-boronic acid pinacol ester, INDOLE-5-BORONIC ACID, PINACOL ESTER, 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, 1H-Indole-5-boronic acid pinacol ester, 1H-Indole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, MFCD03789263, INDOLYL-5-BORONIC ACID PINACOL ESTER, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, (1H-INDOL-5-YL)BORONIC ACID PINACOL ESTER, 5-Indolylboronic acid, pinacol ester, SCHEMBL9918, 5-indole boronic acid pinacol ester, BCP10037, SBB099684, AKOS000283817, GS-6535, PB14363, 5-Indoleboronic acid pinacol ester, 97%, SY021939, DB-009206, CS-0041510, I0590, EN300-212557, Z1741960625, 2-indol-5-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole

Application

This boronate ester serves as a key building block for palladium-catalyzed cross-coupling reactions to create novel indole-containing pharmaceuticals. Researchers utilize it in the synthesis of kinase inhibitors and serotonin receptor modulators. The compound’s stability allows for multistep synthetic transformations in medicinal chemistry programs targeting CNS disorders and oncology therapeutics.

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 (97.7%): 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 (100%)
  • Eye Irrit. 2 (100%)
  • STOT SE 3 (97.7%)

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  • Strictly prohibited: Resale, repackaging, or formulation into commercial products.
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