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

CAS 548797-51-9Formula C13H15BClNO2MW 263.53PubChem 57926113

2-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is a versatile boronic acid pinacol ester, widely employed as a key building block in Suzuki-Miyaura cross-coupling reactions for the synthesis of complex organic compounds in research settings.

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InChIKey: ZOSROBSLLRBHDG-UHFFFAOYSA-NC13H15BClNO2 | MW 263.53

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

833-145-03-Chloro-4-cyanophenylboronic acid pinacol esterZOSROBSLLRBHDG-UHFFFAOYSA-NZB1842BENZONITRILE, 2-CHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-
Show all synonyms
C15973F244108Z18278932692-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile
External Identifiers
RefChem:468922MFCD16996249SCHEMBL748654SCHEMBL30015551DTXSID70728300AKOS016010857MB20307NCGC00662539-01BS-28668SY009355DB-355601CS-0112716EN300-176016

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

Estimated

Estimated / 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

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 (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.

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