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2-(4-Iodophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

CAS 1257649-56-1Formula C11H11BINO4MW 358.93PubChem 71310644

This compound is a MIDA ester of 4-iodophenylboronic acid, serving as a stable and versatile building block for Suzuki-Miyaura cross-coupling reactions and other synthetic transformations in organic chemistry research. Its protected boronic acid form offers improved handling and stability.

Loading RDKit molecule structure...
InChIKey: KIKNJEGAWBNFLW-UHFFFAOYSA-NC11H11BINO4 | MW 358.93

Chemical Identity

Molecular Formula

C11H11BINO4

Molecular Weight

358.93 g/mol

Exact Mass

358.98259

PubChem CID

71310644

SMILES String

CN1CC(=O)OB(c2ccc(I)cc2)OC(=O)C1

Names & Synonyms

4-Iodophenylboronic acid MIDA ester4-Iodophenylboronic acid MIDA ester, 97%
External Identifiers
DTXSID20746271RefChem:252438DTXCID00697015MFCD11215234AKOS022168234AS-2788CS-0443792

Catalog Overview

2-(4-Iodophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, also known as 4-Iodophenylboronic acid MIDA ester, is a protected form of 4-iodophenylboronic acid. MIDA (N-methyliminodiacetic acid) esters are highly valued in organic synthesis for their enhanced stability, crystallinity, and air-stability compared to free boronic acids, making them convenient and robust reagents. The presence of the iodine atom at the para-position of the phenyl ring provides a reactive site for palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura couplings, enabling the efficient formation of new carbon-carbon bonds. This...

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Read more catalog context

2-(4-Iodophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, also known as 4-Iodophenylboronic acid MIDA ester, is a protected form of 4-iodophenylboronic acid. MIDA (N-methyliminodiacetic acid) esters are highly valued in organic synthesis for their enhanced stability, crystallinity, and air-stability compared to free boronic acids, making them convenient and robust reagents. The presence of the iodine atom at the para-position of the phenyl ring provides a reactive site for palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura couplings, enabling the efficient formation of new carbon-carbon bonds. This compound serves as a versatile building block in medicinal chemistry, agrochemical research, and materials science for synthesizing complex molecules and advanced intermediates.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

white solid

Physical State

solid

Melting Point

110.0 °C

Boiling Point

348.0 °C

Density

1.7 g/cm³

Water Solubility

3.31 × 10⁻⁴ mol/L

Flash Point

165.0 °C

Applications / Classifications

Research intermediateCustom synthesis building block

Biological Target Reference

No verified biological target assignment. This compound is listed primarily as a research or synthetic intermediate.

Preliminary Safety-Style Reference

Preliminary

Preliminary safety-style information for reference only. Not a supplier SDS.

Handling and Storage
  • Handle with appropriate personal protective equipment, including chemical-resistant gloves, eye protection, and a lab coat. Use in a well-ventilated area or a certified fume hood to minimize exposure to dust or vapors. Avoid inhalation, ingestion, and contact with skin and eyes. Refer to the Safety Data Sheet (SDS) for comprehensive hazard information, first-aid measures, and safe handling and storage procedures. Store in a cool, dry place, away from incompatible materials.

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