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

CAS 1257649-57-2Formula C11H11BBrNO4MW 311.93PubChem 71310655

2-(2-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, also known as 2-Bromophenylboronic acid MIDA ester, is a functionalized intermediate primarily used in organic synthesis. It serves as a stable and protected boronic acid equivalent, particularly valuable in Suzuki-Miyaura cross-coupling reactions for forming carbon-carbon bonds in research settings.

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

Chemical Identity

Molecular Formula

C11H11BBrNO4

Molecular Weight

311.93 g/mol

Exact Mass

310.99645

PubChem CID

71310655

SMILES String

CN1CC(=O)OB(c2ccccc2Br)OC(=O)C1

Names & Synonyms

2-Bromophenylboronic acid MIDA ester2-(2-Bromophenyl)-6-methyl-1,3,6,2-dioxazaboracane-4,8-dione2-Bromophenylboronic acid MIDA ester, 95%Boron, (2-bromophenyl)[N-[(carboxy-kappaO)methyl]-N-methylglycinato(2-)-kappaN,kappaO]-, (T-4)-
External Identifiers
DTXSID40746278RefChem:250496DTXCID70697022MFCD11215210SY038356

Catalog Overview

2-(2-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, with CAS 1257649-57-2, is a versatile organoboron compound. It is a MIDA (N-methyliminodiacetic acid) ester of 2-bromophenylboronic acid, characterized by its unique dioxazaborocane ring structure. This compound acts as a stable and protected form of 2-bromophenylboronic acid, which is otherwise prone to decomposition or undesired side reactions. The presence of both a boronate ester and a bromo-substituted phenyl group makes it a key building block in complex organic synthesis, especially for palladium-catalyzed cross-coupling reactions like the Suzuki-Miyaura...

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Read more catalog context

2-(2-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione, with CAS 1257649-57-2, is a versatile organoboron compound. It is a MIDA (N-methyliminodiacetic acid) ester of 2-bromophenylboronic acid, characterized by its unique dioxazaborocane ring structure. This compound acts as a stable and protected form of 2-bromophenylboronic acid, which is otherwise prone to decomposition or undesired side reactions. The presence of both a boronate ester and a bromo-substituted phenyl group makes it a key building block in complex organic synthesis, especially for palladium-catalyzed cross-coupling reactions like the Suzuki-Miyaura coupling, enabling the introduction of a 2-bromophenyl moiety into various molecular architectures. It is intended for research use only.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White solid

Physical State

Solid

Melting Point

110.0 °C

Boiling Point

346.0 °C

Density

1.5 g/cm³

Water Solubility

1.58 × 10⁻³ mol/L

Flash Point

230.0 °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
  • For research use only. Handle 2-(2-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione in a well-ventilated area or fume hood. Wear appropriate personal protective equipment, including gloves, eye protection, and a lab coat. Avoid inhalation, ingestion, and skin contact. In case of contact, wash thoroughly with soap and water. Consult the Safety Data Sheet (SDS) for detailed hazard information and emergency procedures.

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