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

CAS 1246632-86-9Formula C13H15BClNO2MW 263.53PubChem 68182102

This compound is a chlorinated benzonitrile derivative featuring a pinacol boronate ester group. It is primarily used as a versatile building block in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions for forming carbon-carbon bonds.

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

Chemical Identity

Molecular Formula

C13H15BClNO2

Molecular Weight

263.53 g/mol

Exact Mass

263.088437

PubChem CID

68182102

SMILES String

CC1(C)OB(c2ccc(Cl)cc2C#N)OC1(C)C

Names & Synonyms

Benzonitrile, 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileG41440F758008Z2049759798
External Identifiers
SCHEMBL11971323SCHEMBL30722717DTXSID701160127MFCD18779812DB-100260CS-0368477EN300-12602381

Catalog Overview

5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is an organoboron compound characterized by a chlorobenzonitrile core substituted with a pinacol boronate ester at the ortho position to the nitrile group and a chlorine atom at the meta position. With a molecular formula of C13H15BClNO2 and a molecular weight of 263.53 g/mol, this compound serves as a key functionalized intermediate in synthetic chemistry. The pinacol boronate group is highly reactive in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, enabling the introduction of the substituted benzonitrile moiety into complex...

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5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is an organoboron compound characterized by a chlorobenzonitrile core substituted with a pinacol boronate ester at the ortho position to the nitrile group and a chlorine atom at the meta position. With a molecular formula of C13H15BClNO2 and a molecular weight of 263.53 g/mol, this compound serves as a key functionalized intermediate in synthetic chemistry. The pinacol boronate group is highly reactive in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, enabling the introduction of the substituted benzonitrile moiety into complex molecular structures. The nitrile group can be further transformed, and the chlorine atom provides another site for potential functionalization or substitution reactions. This makes it a valuable reagent for constructing diverse organic molecules, including potential pharmaceutical intermediates and materials science compounds, within a research-use context.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White to off-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

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 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 of dust or vapors. 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 comprehensive safety information before handling.

Related Products / Graph Discovery

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