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Atomfair 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole C19H36BNO2Si CAS 365564-11-0

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole (CAS No. 365564-11-0) is a highly specialized organoboron compound with the molecular formula C19H36BNO2Si. This advanced reagent features a unique combination of a pyrrole ring, a dioxaborolane group, and a tris(propan-2-yl)silyl protecting group, making it an invaluable tool for researchers in synthetic organic chemistry, particularly in Suzuki-Miyaura cross-coupling reactions. The compound is supplied as a high-purity solid, ensuring consistent performance in demanding applications. Its well-defined structure and stability under various reaction conditions make it ideal for the synthesis of complex heterocyclic compounds and pharmaceutical intermediates. Proper storage under inert conditions is recommended to maintain its reactivity and shelf life.

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Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole (CAS No. 365564-11-0) is a highly specialized organoboron compound with the molecular formula C19H36BNO2Si. This advanced reagent features a unique combination of a pyrrole ring, a dioxaborolane group, and a tris(propan-2-yl)silyl protecting group, making it an invaluable tool for researchers in synthetic organic chemistry, particularly in Suzuki-Miyaura cross-coupling reactions. The compound is supplied as a high-purity solid, ensuring consistent performance in demanding applications. Its well-defined structure and stability under various reaction conditions make it ideal for the synthesis of complex heterocyclic compounds and pharmaceutical intermediates. Proper storage under inert conditions is recommended to maintain its reactivity and shelf life.

Properties

  • CAS Number: 365564-11-0
  • Complexity: 413
  • IUPAC Name: triisopropyl-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane
  • InChI: InChI=1S/C19H36BNO2Si/c1-14(2)24(15(3)4,16(5)6)21-12-11-17(13-21)20-22-18(7,8)19(9,10)23-20/h11-16H,1-10H3
  • InChI Key: GWFIZBYDIHGZRJ-UHFFFAOYSA-N
  • Exact Mass: 349.2608361
  • Molecular Formula: C19H36BNO2Si
  • Molecular Weight: 349.4
  • SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(C=C2)[Si](C(C)C)(C(C)C)C(C)C
  • Topological: 23.4
  • Monoisotopic Mass: 349.2608361
  • Synonyms: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-[TRIS(1-METHYLETHYL)SILYL]-1H-PYRROLE, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(1-methylethyl)silyl)-1H-pyrrole, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole, 969-621-0, 365564-11-0, 1-TRIISOPROPYLSILANYL-1H-PYRROLE-3-BORONIC ACID PINACOL ESTER, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole, 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole, tri(propan-2-yl)-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane, MFCD08063117, 1-(TRIISOPROPYLSILYL)-1H-PYRROLE-3-BORONIC ACID PINACOL ESTER, N-TIPS PYRROLE-3-BORONIC ACID PINACOL ESTER, C19H36BNO2Si, SCHEMBL28739, 1-(Triisopropylsilyl)pyrrole-3-boronic Acid Pinacol Ester, DTXSID60466340, GWFIZBYDIHGZRJ-UHFFFAOYSA-N, QPA56411, (1-(TRIISOPROPYLSILYL)-1H-PYRROL-3-YL)BORONIC ACID PINACOL ESTER, AKOS015946696, PB20241, Pyrrole-3-boronic acid, pinacol ester;, AS-55586, DA-30511, SY025049, CS-0051659, EN300-212692, 1-Triisopropylsilanyl-1H-pyrrole-3-boronic acid, pinacol ester, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-pyrrole, 1H-PYRROLE, 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-[TRIS(1-METHYLETHYL)SILYL]-

Application

This compound is primarily used as a key intermediate in palladium-catalyzed cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex organic syntheses. It finds particular utility in medicinal chemistry for the construction of biologically active pyrrole-containing compounds. The tris(propan-2-yl)silyl group enhances the compound’s stability while allowing for selective deprotection when needed. Researchers also employ this reagent in materials science for the development of novel conjugated polymers with tailored electronic properties.

Safety and Hazards

GHS Hazard Statements

  • H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
  • H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
  • H318 (100%): Causes serious eye damage [Danger 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, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

  • Acute Tox. 4 (100%)
  • Skin Irrit. 2 (100%)
  • Eye Dam. 1 (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.

Disclaimer

Intended Use & Restrictions

This product is sold exclusively for laboratory research, analytical testing, or non-commercial purposes.

  • Strictly prohibited: Resale, repackaging, or formulation into commercial products.
  • Not approved for human/animal use, diagnostics, or manufacturing (including pharmaceuticals, agrochemicals, or consumer goods).

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Certain molecules may be protected by active patents or regulatory restrictions.

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  • Use this product only as permitted by law.
  • Indemnify Atomfair LLC against all claims arising from misuse, patent infringement, or regulatory violations.

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