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Atomfair (E)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane trans-Crotylboronic acid pinacol ester, E-CrotylBPin C10H19BO2 CAS 69611-02-5

(E)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 69611-02-5) is a high-purity organoboron compound widely used in organic synthesis and pharmaceutical research. This reagent, with the molecular formula C10H19BO2, is a stable, crystalline solid under standard conditions, offering excellent reactivity in cross-coupling reactions such as Suzuki-Miyaura couplings. Its IUPAC name, 2-[(E)-but-2-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane , reflects its structural precision, featuring a pinacol-protected boronate ester group and a trans-crotyl moiety. This compound is rigorously tested for purity (typically ≥95% by GC or NMR) and is packaged under inert gas to ensure stability. Ideal for researchers seeking reliable boron-based building blocks for C-C bond formation, catalysis, or material science applications.

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Description

(E)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 69611-02-5) is a high-purity organoboron compound widely used in organic synthesis and pharmaceutical research. This reagent, with the molecular formula C10H19BO2, is a stable, crystalline solid under standard conditions, offering excellent reactivity in cross-coupling reactions such as Suzuki-Miyaura couplings. Its IUPAC name, 2-[(E)-but-2-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, reflects its structural precision, featuring a pinacol-protected boronate ester group and a trans-crotyl moiety. This compound is rigorously tested for purity (typically ≥95% by GC or NMR) and is packaged under inert gas to ensure stability. Ideal for researchers seeking reliable boron-based building blocks for C-C bond formation, catalysis, or material science applications.

Properties

  • CAS Number: 69611-02-5
  • Complexity: 193
  • IUPAC Name: 2-[(E)-but-2-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • InChI: InChI=1S/C10H19BO2/c1-6-7-8-11-12-9(2,3)10(4,5)13-11/h6-7H,8H2,1-5H3/b7-6+
  • InChI Key: ARSSMJZIAKUXEW-VOTSOKGWSA-N
  • Exact Mass: 182.1478100
  • Molecular Formula: C10H19BO2
  • Molecular Weight: 182.07
  • SMILES: B1(OC(C(O1)(C)C)(C)C)C/C=C/C
  • Topological: 18.5
  • Monoisotopic Mass: 182.1478100
  • Synonyms: 69611-02-5, trans-Crotylboronic acid pinacol ester, (E)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 167773-12-8, E-Crotylboronic acid pinacol ester, 2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-[(E)-but-2-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-[(2E)-BUT-2-EN-1-YL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, 1,3,2-Dioxaborolane, 2-(2-buten-1-yl)-4,4,5,5-tetramethyl-, 2-[(2Z)-But-2-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, SCHEMBL11941627, ARSSMJZIAKUXEW-VOTSOKGWSA-N, AKOS030623157, AS-63883, DB-319266, CS-0129386, trans-Crotylboronic acid pinacol ester, 95%, E76842

Application

This compound is primarily employed in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex organic molecules with high stereoselectivity. It serves as a key intermediate in pharmaceutical research for constructing bioactive compounds with olefinic motifs. Additionally, it is used in materials science for designing boron-containing polymers and functionalized surfaces.

Safety and Hazards

GHS Hazard Statements

  • H227 (100%): Combustible liquid [Warning Flammable liquids]
  • 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

  • P210, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, and P501

Hazard Classes and Categories

  • Flam. Liq. 4 (100%)
  • Skin Irrit. 2 (100%)
  • Eye Irrit. 2A (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).

Patent & Regulatory Compliance

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

  • Buyers must independently verify patent status (e.g., via USPTO/EPO/CNIPA) and comply with local laws.
  • Atomfair LLC does not provide legal assurances regarding patent non-infringement or jurisdictional compliance.

Liability Release

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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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