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Atomfair 2-(2-Methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane C13H18BNO5 CAS 677746-34-8

2-(2-Methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 677746-34-8) is a high-purity boronic ester compound widely used in organic synthesis and pharmaceutical research. With the molecular formula C13H18BNO5, this reagent serves as a versatile building block for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecular architectures. The presence of both methoxy and nitro functional groups enhances its reactivity and selectivity in palladium-catalyzed transformations. This compound is supplied as a crystalline solid with exceptional stability under inert conditions, ensuring reliable performance in sensitive synthetic applications. Ideal for researchers in medicinal chemistry and materials science, it is rigorously tested for purity (typically >95%…

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Description

2-(2-Methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 677746-34-8) is a high-purity boronic ester compound widely used in organic synthesis and pharmaceutical research. With the molecular formula C13H18BNO5, this reagent serves as a versatile building block for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecular architectures. The presence of both methoxy and nitro functional groups enhances its reactivity and selectivity in palladium-catalyzed transformations. This compound is supplied as a crystalline solid with exceptional stability under inert conditions, ensuring reliable performance in sensitive synthetic applications. Ideal for researchers in medicinal chemistry and materials science, it is rigorously tested for purity (typically >95% by HPLC) and packaged under nitrogen to prevent degradation.

Properties

  • CAS Number: 677746-34-8
  • Complexity: 365
  • IUPAC Name: 2-(2-methoxy-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • InChI: InChI=1S/C13H18BNO5/c1-12(2)13(3,4)20-14(19-12)10-8-9(15(16)17)6-7-11(10)18-5/h6-8H,1-5H3
  • InChI Key: DLBHUTKTPNNASR-UHFFFAOYSA-N
  • Exact Mass: 279.1278028
  • Molecular Formula: C13H18BNO5
  • Molecular Weight: 279.10
  • SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)[N+](=O)[O-])OC
  • Topological: 73.5
  • Monoisotopic Mass: 279.1278028
  • Synonyms: 677746-34-8, 2-(2-Methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 968-471-3, 2-Methoxy-5-nitrophenylboronic acid pinacol ester, MFCD20327978, SCHEMBL20303461, CCB74634, XH0344, 2-(2-methoxy-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, BS-29328, SY057009, CS-0107359, D76731, EN300-7421963, Z2049993186

Application

This boronic ester is primarily employed in Suzuki-Miyaura cross-coupling reactions to synthesize biaryl compounds for pharmaceutical intermediates and functional materials. Its electron-withdrawing nitro group facilitates oxidative addition in palladium-catalyzed processes, while the pinacol ester moiety ensures improved handling stability compared to free boronic acids. Researchers utilize it to construct conjugated systems in OLED materials and bioactive molecules. The methoxy substituent offers additional site-specific modification opportunities in multi-step syntheses.

Safety and Hazards

GHS Hazard Statements

  • H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
  • 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, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

  • Acute Tox. 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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