Description

2-Chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (CAS: 883899-06-7) is a high-purity boronic ester derivative with the molecular formula C₁₂H₁₃BClNO₂. This compound features a reactive boronate group stabilized by a neopentyl glycol (5,5-dimethyl-1,3,2-dioxaborinane) moiety, making it an excellent intermediate for Suzuki-Miyaura cross-coupling reactions. The presence of both chloro and cyano substituents on the benzene ring enhances its versatility in organic synthesis, particularly in pharmaceutical and agrochemical research. With a purity of ≥95% (HPLC), this reagent is ideal for constructing complex aromatic frameworks. Store under inert conditions to maintain stability.

Properties

• CAS Number: 883899-06-7
• Complexity: 318
• IUPAC Name: 2-chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile
• InChI: InChI=1S/C12H13BClNO2/c1-12(2)7-16-13(17-8-12)10-4-3-5-11(14)9(10)6-15/h3-5H,7-8H2,1-2H3
• InChI Key: DILJKRGCLPAOLL-UHFFFAOYSA-N
• Exact Mass: 249.0727865
• Molecular Formula: C12H13BClNO2
• Molecular Weight: 249.50
• SMILES: B1(OCC(CO1)(C)C)C2=C(C(=CC=C2)Cl)C#N
• Topological: 42.3
• Monoisotopic Mass: 249.0727865
• Synonyms: 883899-06-7, 2-chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, 3-CHLORO-2-CYANOPHENYLBORONIC ACID NEOPENTYL GLYCOL ESTER, MFCD08669560, DTXSID40469612, Benzonitrile, 2-chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-, AKOS015999636, AB45904, BS-22884, CS-0174393, E90145

Application

2-Chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile is widely used as a key building block in palladium-catalyzed cross-coupling reactions, enabling the synthesis of biaryl structures for drug discovery. Its boronate ester group offers improved stability compared to boronic acids, simplifying handling and storage. Researchers leverage this compound in the development of kinase inhibitors and other bioactive molecules. It is also employed in material science for creating conjugated polymers with tailored electronic properties.

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