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

CAS 1035235-29-0Formula C13H15BFNO2MW 247.07PubChem 44755210

3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is a fluorinated benzonitrile derivative featuring a pinacol boronate ester group. It is primarily used as a versatile building block in organic synthesis, particularly for Suzuki-Miyaura cross-coupling reactions to introduce fluorinated aryl groups into complex molecular structures for research purposes.

Loading RDKit molecule structure...
InChIKey: FEUINZSEHIJUBU-UHFFFAOYSA-NC13H15BFNO2 | MW 247.07

Chemical Identity

Molecular Formula

C13H15BFNO2

Molecular Weight

247.07 g/mol

Exact Mass

247.117987

PubChem CID

44755210

SMILES String

CC1(C)OB(c2ccc(C#N)cc2F)OC1(C)C

Names & Synonyms

3-fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile690-897-04-CYANO-2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER4-Cyano-2-fluorophenylboronic acid pinacol ester4-Cyano-2-fluorobenzeneboronic acid, pinacol ester
Show all synonyms
4-Cyano-2-fluorophenylboronicAcidPinacolEsterFEUINZSEHIJUBU-UHFFFAOYSA-NAC17753-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile3-Cyano-2-fluorobenzeneboronic acid, pinacol esterF2284074-CYANO-2-FLUOROBENZENEBORONIC ACID PINACOL ESTERZ17419808724-Cyano-2-fluorophenylboronic acid pinacol ester, AldrichCPR3-fluoro-4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzenecarbonitrile
External Identifiers
DTXSID10660654RefChem:501708DTXCID50611403MFCD09998162SCHEMBL156525SCHEMBL29358185SBB100210AKOS015960168MB08382PS-9709SY032567EN300-316723

Catalog Overview

3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, with CAS 1035235-29-0 and molecular formula C13H15BFNO2, is a highly functionalized intermediate. It combines a fluorinated benzonitrile core with a pinacol boronate ester. The boronate ester group makes it an excellent reagent for carbon-carbon bond formation, especially in Suzuki-Miyaura coupling reactions, allowing for the facile introduction of a 3-fluoro-4-cyanophenyl moiety into various molecular architectures. The presence of fluorine can impart unique physicochemical properties, such as altered pKa, lipophilicity, and metabolic stability, to target...

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3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, with CAS 1035235-29-0 and molecular formula C13H15BFNO2, is a highly functionalized intermediate. It combines a fluorinated benzonitrile core with a pinacol boronate ester. The boronate ester group makes it an excellent reagent for carbon-carbon bond formation, especially in Suzuki-Miyaura coupling reactions, allowing for the facile introduction of a 3-fluoro-4-cyanophenyl moiety into various molecular architectures. The presence of fluorine can impart unique physicochemical properties, such as altered pKa, lipophilicity, and metabolic stability, to target molecules. The nitrile group offers further synthetic handles for transformations like hydrolysis to carboxylic acids or reduction to amines. This compound is valuable in medicinal chemistry and materials science research for synthesizing complex organic molecules.

Physical Data

Estimated

Estimated / predicted physical property values for catalog reference.

Appearance

White solid

Physical State

Solid

Melting Point

47.0 °C

Boiling Point

272.0 °C

Density

1.3 g/cm³

Water Solubility

1.32 × 10⁻³ 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 under a 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 hazard information and safe handling procedures. This product is for research use only and not for human or animal therapeutic or diagnostic use.

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