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4-Chloro-2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

CAS 2223054-28-0Formula C14H17BClNO2MW 277.55PubChem 133635617

4-Chloro-2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is a functionalized boronic acid pinacol ester, primarily utilized as a versatile building block in organic synthesis. It is particularly valuable for Suzuki-Miyaura cross-coupling reactions, enabling the formation of new carbon-carbon bonds in the synthesis of complex molecules for research purposes.

Loading RDKit molecule structure...
InChIKey: RGJWKKYKGLXWQJ-UHFFFAOYSA-NC14H17BClNO2 | MW 277.55

Chemical Identity

Molecular Formula

C14H17BClNO2

Molecular Weight

277.55 g/mol

Exact Mass

277.104087

PubChem CID

133635617

IUPAC Name

4-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

SMILES String

Cc1cc(Cl)c(B2OC(C)(C)C(C)(C)O2)cc1C#N

Names & Synonyms

2-Chloro-5-cyano-4-methylphenylboronic acid pinacol ester
External Identifiers
CS-31211EN300-12732236

Catalog Overview

4-Chloro-2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, identified by CAS 2223054-28-0, is a meticulously synthesized organic compound featuring a chlorinated, methylated, and cyanated benzene ring substituted with a pinacol boronate group. With a molecular formula of C14H17BClNO2 and a molecular weight of 277. 55, this compound serves as a key functionalized intermediate. Its boronic ester functionality makes it highly reactive in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, facilitating the introduction of aryl groups into various synthetic pathways.

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Read more catalog context

4-Chloro-2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, identified by CAS 2223054-28-0, is a meticulously synthesized organic compound featuring a chlorinated, methylated, and cyanated benzene ring substituted with a pinacol boronate group. With a molecular formula of C14H17BClNO2 and a molecular weight of 277.55, this compound serves as a key functionalized intermediate. Its boronic ester functionality makes it highly reactive in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, facilitating the introduction of aryl groups into various synthetic pathways. The presence of a nitrile group and a chlorine atom provides additional sites for further chemical transformations, making it a versatile reagent for constructing diverse chemical structures in academic and industrial research settings.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White to off-white crystalline powder

Physical State

Solid

Melting Point

140.0 °C

Boiling Point

400.0 °C

Density

1.2 g/cm³

Water Solubility

Insoluble

Flash Point

175.0 °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 4-Chloro-2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile with appropriate personal protective equipment, including gloves, eye protection, and a lab coat. Use in a well-ventilated area or under a 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. Refer to the Safety Data Sheet (SDS) for comprehensive safety information before use.

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