Chemical Identity
Molecular Formula
C13H15BClNO2
Molecular Weight
263.53 g/mol
Exact Mass
263.088437
PubChem CID
57926113
IUPAC Name
2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
SMILES String
CC1(C)OB(c2ccc(C#N)c(Cl)c2)OC1(C)C
Names & Synonyms
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External Identifiers
Catalog Overview
2-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is an organic compound featuring a chlorobenzonitrile core substituted with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (pinacol boronic ester) group. This structure makes it a highly valuable reagent in synthetic organic chemistry, particularly for forming new carbon-carbon bonds. The pinacol boronic ester moiety is stable and readily participates in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura reaction, allowing for the introduction of diverse aryl or heteroaryl groups. The presence of the chloro and cyano functionalities provides...
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2-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is an organic compound featuring a chlorobenzonitrile core substituted with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (pinacol boronic ester) group. This structure makes it a highly valuable reagent in synthetic organic chemistry, particularly for forming new carbon-carbon bonds. The pinacol boronic ester moiety is stable and readily participates in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura reaction, allowing for the introduction of diverse aryl or heteroaryl groups. The presence of the chloro and cyano functionalities provides additional handles for further chemical transformations, making this compound a flexible intermediate for constructing intricate molecular architectures relevant to medicinal chemistry, agrochemicals, and materials science research.
Physical Data
EstimatedEstimated / predicted physical property values for catalog reference.
Appearance
White to off-white crystalline solid
Physical State
Solid
Melting Point
56.0 °C
Boiling Point
307.0 °C
Density
1.3 g/cm³
Water Solubility
2.95 × 10⁻⁴ mol/L
Flash Point
200.0 °C
Applications / Classifications
Biological Target Reference
No verified biological target assignment. This compound is listed primarily as a research or synthetic intermediate.
Preliminary Safety-Style Reference
PreliminaryPreliminary safety-style information for reference only. Not a supplier SDS.
Handling and Storage
- Handle with appropriate personal protective equipment (PPE) including gloves, eye protection, and a lab coat. Work 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. Dispose of waste according to local regulations for chemical waste.
Related Products / Graph Discovery
Related products, derivatives, keywords, and application cues for catalog discovery.
Related products and analog discovery will be available as catalog graph data is expanded.