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

CAS 943552-04-3Formula C11H11BBrNO4MW 311.93PubChem 44542259

2-(4-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, also known as 4-Bromophenylboronic acid MIDA ester, is a functionalized boronate ester. This compound serves as a stable and versatile building block in organic synthesis, particularly for Suzuki-Miyaura cross-coupling reactions, where it acts as a protected equivalent of 4-bromophenylboronic acid for research applications.

Loading RDKit molecule structure...
InChIKey: ZKMPNCNELZIKDC-UHFFFAOYSA-NC11H11BBrNO4 | MW 311.93

Chemical Identity

Molecular Formula

C11H11BBrNO4

Molecular Weight

311.93 g/mol

Exact Mass

310.99645

PubChem CID

44542259

SMILES String

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

Names & Synonyms

4-Bromophenylboronic acid MIDA ester4-Bromophenylboronic acid MIDA ester, 97%
External Identifiers
DTXSID70659281RefChem:252038DTXCID30610030MFCD11215230AKOS022168233AS-2802

Catalog Overview

2-(4-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, with CAS 943552-04-3, is a MIDA (N-methyliminodiacetic acid) boronate ester featuring a 4-bromophenyl group. MIDA boronates are cyclic boronate esters known for their enhanced stability compared to free boronic acids, making them easier to handle and purify. The presence of the bromine atom on the phenyl ring provides a reactive site for further functionalization, while the MIDA protecting group allows for controlled release of the boronic acid functionality under specific conditions, typically mild basic hydrolysis. This compound is a valuable intermediate in the...

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Read more catalog context

2-(4-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, with CAS 943552-04-3, is a MIDA (N-methyliminodiacetic acid) boronate ester featuring a 4-bromophenyl group. MIDA boronates are cyclic boronate esters known for their enhanced stability compared to free boronic acids, making them easier to handle and purify. The presence of the bromine atom on the phenyl ring provides a reactive site for further functionalization, while the MIDA protecting group allows for controlled release of the boronic acid functionality under specific conditions, typically mild basic hydrolysis. This compound is a valuable intermediate in the synthesis of complex organic molecules, enabling sequential cross-coupling reactions for research purposes.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

white solid

Physical State

solid

Melting Point

105.0 °C

Boiling Point

346.0 °C

Density

1.6 g/cm³

Water Solubility

1.58 × 10⁻³ mol/L

Flash Point

200.0 °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 gloves, eye protection, and a lab coat. Use in a well-ventilated area or fume hood to avoid inhalation. Avoid contact with skin and eyes. In case of contact, rinse immediately with plenty of water. Store in a cool, dry place, away from incompatible materials. Consult the Safety Data Sheet (SDS) for detailed hazard information and precautions before use.

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