Description

1-(Triisopropylsilyl)pyrrole-3-boronic acid (CAS No. 138900-55-7) is a high-purity boronic acid derivative featuring a triisopropylsilyl (TIPS) protecting group, designed for advanced synthetic applications in organic and medicinal chemistry. With the molecular formula C₁₃H₂₆BNO₂Si, this compound serves as a versatile building block for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecule synthesis. The TIPS group enhances stability and solubility, making it ideal for air- and moisture-sensitive reactions. This reagent is rigorously tested for quality, ensuring optimal performance in research and industrial settings. Suitable for use in pharmaceuticals, agrochemicals, and materials science, it is available in various packaging options to meet your laboratory needs.

Properties

• CAS Number: 138900-55-7
• Complexity: 250
• IUPAC Name: (1-triisopropylsilylpyrrol-3-yl)boronic acid
• InChI: InChI=1S/C13H26BNO2Si/c1-10(2)18(11(3)4,12(5)6)15-8-7-13(9-15)14(16)17/h7-12,16-17H,1-6H3
• InChI Key: HUBVAOMVEMGRFA-UHFFFAOYSA-N
• Exact Mass: 267.1825858
• Molecular Formula: C13H26BNO2Si
• Molecular Weight: 267.25
• SMILES: B(C1=CN(C=C1)[Si](C(C)C)(C(C)C)C(C)C)(O)O
• Topological: 45.4
• Monoisotopic Mass: 267.1825858
• Synonyms: 138900-55-7, 1-(Triisopropylsilyl)pyrrole-3-boronic acid, (1-(Triisopropylsilyl)-1H-pyrrol-3-yl)boronic acid, [1-tri(propan-2-yl)silylpyrrol-3-yl]boronic acid, MFCD01114667, 1-(TRIISOPROPYLSILYL)-1H-PYRROLE-3-BORONIC ACID, {1-[tris(propan-2-yl)silyl]-1H-pyrrol-3-yl}boronic acid, 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid, [1-[tris(1-Methylethyl)silyl]-1H-pyrrol-3-yl]-boronic acid, Boronic acid, B-[1-[tris(1-methylethyl)silyl]-1H-pyrrol-3-yl]-, 1-[Tris(isopropyl)silyl]-1H-pyrrole-3-boronic acid, [1-(triisopropylsilyl)-1H-pyrrol-3-yl]boronic acid, 3-Borono-1-[tris(isopropyl)silyl]-1H-pyrrole, SCHEMBL101282, DTXSID50376883, HUBVAOMVEMGRFA-UHFFFAOYSA-N, Boronic acid, [1-[tris(1-methylethyl)silyl]-1H-pyrrol-3-yl]-, AKOS004116477, FT10307, PB18534, SB10540, 1-triisopropylsilylpyrrol-3-boronic acid, 1-triisopropylsilylpyrrole-3-boronic acid, AC-30993, AS-50422, SY062735, N-triisopropylsilyl-3-pyrrole boronic acid, DB-009139, EN300-96648, triisopropylsilanyl-1H-pyrrole-3-boronic acid, 1-(Triisopropyl silyl) pyrrole-3-boronic acid, P10171, 1-triisopropylsilanyl-1H-pyrrole-3-boronic acid, 1-(triisopropylsilanyl)-1H-pyrrole-3-boronic acid, 1-(triisopropylsilyl)pyrrole-3-boronic acid, AldrichCPR, {1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}boronic acid, {1-[tris(1-methylethyl)silyl]-1H-pyrrol-3-yl}boronic acid

Application

1-(Triisopropylsilyl)pyrrole-3-boronic acid is widely used in palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura couplings, to construct biaryl and heteroaryl structures prevalent in drug discovery. Its TIPS-protected pyrrole core enables selective functionalization, making it valuable for synthesizing pharmaceutical intermediates and functional materials. Researchers also employ it in the development of organic electronic materials due to its stability and reactivity under diverse conditions.

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