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

CAS 863868-19-3Formula C13H15BClNO2MW 263.53PubChem 70851456

4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is a versatile research chemical featuring a chlorobenzonitrile core functionalized with a pinacol boronate ester. It serves as a key building block in organic synthesis, particularly for Suzuki-Miyaura cross-coupling reactions, enabling the formation of new carbon-carbon bonds in the development of complex molecules for various research applications.

Loading RDKit molecule structure...
InChIKey: GCMXNGTXQFEURI-UHFFFAOYSA-NC13H15BClNO2 | MW 263.53

Chemical Identity

Molecular Formula

C13H15BClNO2

Molecular Weight

263.53 g/mol

Exact Mass

263.088437

PubChem CID

70851456

SMILES String

CC1(C)OB(c2cc(Cl)ccc2C#N)OC1(C)C

Names & Synonyms

967-250-9Benzonitrile, 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileF83794F758001
Show all synonyms
4-CHLORO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZONITRILE
External Identifiers
RefChem:520925MFCD18729918SCHEMBL13183400CS-31054DB-195435CS-0368462EN300-12595373

Catalog Overview

4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, with CAS 863868-19-3 and molecular formula C13H15BClNO2, is a highly functionalized aromatic compound. It incorporates a chlorine atom and a nitrile group on a benzene ring, alongside a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (pinacol boronate) moiety. This structure makes it an excellent reagent for palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, where the boronate ester acts as a nucleophilic coupling partner. The presence of the nitrile group allows for further derivatization, including hydrolysis to carboxylic acids or...

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4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, with CAS 863868-19-3 and molecular formula C13H15BClNO2, is a highly functionalized aromatic compound. It incorporates a chlorine atom and a nitrile group on a benzene ring, alongside a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (pinacol boronate) moiety. This structure makes it an excellent reagent for palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, where the boronate ester acts as a nucleophilic coupling partner. The presence of the nitrile group allows for further derivatization, including hydrolysis to carboxylic acids or reduction to amines, while the chloro substituent can also participate in other coupling reactions or nucleophilic aromatic substitutions. This compound is primarily intended for research and development purposes in synthetic organic chemistry.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White solid

Physical State

Solid

Melting Point

56.0 °C

Boiling Point

307.0 °C

Density

1.3 g/cm³

Water Solubility

2.63 × 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 4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile in a well-ventilated area or fume hood. Wear appropriate personal protective equipment, including safety goggles, gloves, and a lab coat. Avoid inhalation of dust or vapors, and prevent contact with skin and eyes. In case of contact, rinse thoroughly with 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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