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

CAS 1220696-59-2Formula C14H16BF2NO2MW 279.09PubChem 59535357

This is a difluoromethylated benzonitrile derivative featuring a boronic ester (pinacolborane) group. It serves as a versatile building block in organic synthesis, particularly for Suzuki-Miyaura cross-coupling reactions, enabling the introduction of difluoromethylated aryl groups for research purposes.

Loading RDKit molecule structure...
InChIKey: OHECEKWRPPLHPJ-UHFFFAOYSA-NC14H16BF2NO2 | MW 279.09

Chemical Identity

Molecular Formula

C14H16BF2NO2

Molecular Weight

279.09 g/mol

Exact Mass

279.124215

PubChem CID

59535357

SMILES String

CC1(C)OB(c2cc(C#N)cc(C(F)F)c2)OC1(C)C

Names & Synonyms

TQU0174
External Identifiers
SCHEMBL2432585DTXSID601137515

Catalog Overview

3-(Difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, identified by CAS 1220696-59-2, is a highly functionalized organic compound. It combines a difluoromethyl group, a cyano group, and a pinacolborane moiety on a benzene ring. The boronic ester functionality makes it an excellent reagent for carbon-carbon bond formation, especially in palladium-catalyzed Suzuki-Miyaura coupling reactions, allowing for the facile attachment of the difluoromethylated benzonitrile scaffold to various organic substrates. The difluoromethyl group can impart unique physicochemical properties, such as lipophilicity and...

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Read more catalog context

3-(Difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, identified by CAS 1220696-59-2, is a highly functionalized organic compound. It combines a difluoromethyl group, a cyano group, and a pinacolborane moiety on a benzene ring. The boronic ester functionality makes it an excellent reagent for carbon-carbon bond formation, especially in palladium-catalyzed Suzuki-Miyaura coupling reactions, allowing for the facile attachment of the difluoromethylated benzonitrile scaffold to various organic substrates. The difluoromethyl group can impart unique physicochemical properties, such as lipophilicity and metabolic stability, to target molecules, while the nitrile group offers further synthetic handles for transformations like hydrolysis to carboxylic acids or reduction to amines. This compound is primarily intended for research and development applications in synthetic chemistry.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White to off-white crystalline powder

Physical State

Solid

Melting Point

87.0 °C

Boiling Point

288.0 °C

Density

1.35 g/cm³

Water Solubility

1.51 × 10⁻⁴ mol/L

Flash Point

135.0 °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 safety information before use. This product is for research use only and not for human or animal therapeutic or diagnostic use.

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