[4-[(Pyridin-2-yl)carbamoyl]phenyl]boronic acid
[CAS 850568-25-1]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: [4-[(Pyridin-2-yl)carbamoyl]phenyl]boronic acid
• Molecular Formula: C₁₂H₁₁BN₂O₃
• Molecular Weight: 242.04
• CAS Registry Number: 850568-25-1
• EC Number: 689-936-4
• SMILES: B(C1=CC=C(C=C1)C(=O)NC2=CC=CC=N2)(O)O

Properties

• Solubility: Slightly soluble (1.8 g/L) (25 $degree$C), Calc.^*
• Density: 1.33$+/-$0.1 g/cm³ (20 $degree$C 760 Torr), Calc.^*
• Melting point: 124 - 128 $degree$C (Expl.)
• Index of refraction: 1.627 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H341
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

[4-[(Pyridin-2-yl)carbamoyl]phenyl]boronic acid is a functionalized aromatic boronic acid in which a phenyl ring is substituted at the 4-position with a pyridin-2-yl carbamoyl group and a boronic acid moiety (–B(OH)₂). Boronic acids are widely used in organic synthesis, medicinal chemistry, and material science due to their unique ability to undergo reversible covalent interactions, participate in cross-coupling reactions, and form hydrogen bonds. The presence of a carbamoyl-linked pyridine provides additional hydrogen-bonding sites and electron-withdrawing effects that influence reactivity and binding properties.

Structurally, the molecule consists of a phenyl ring bearing a boronic acid at the para position relative to a carbamoyl group attached to a pyridin-2-yl substituent. The boronic acid contains a trigonal planar boron atom bonded to two hydroxyl groups, which can form esters with diols or participate in Suzuki–Miyaura cross-coupling reactions. The pyridinyl carbamoyl group introduces both planarity and hydrogen-bonding capability, which can stabilize interactions in both synthetic and biological contexts. The electronic effects of the pyridine nitrogen and the carbamoyl oxygen influence the acidity of the boronic acid and modulate its reactivity in coupling reactions.

The synthesis of [4-[(pyridin-2-yl)carbamoyl]phenyl]boronic acid typically involves amide formation between 4-aminophenylboronic acid and 2-pyridinecarboxylic acid derivatives using standard coupling agents, followed by purification under conditions that preserve the sensitive boronic acid functionality. Careful control of solvent, temperature, and pH is required to prevent boronic acid oxidation or undesired side reactions. The product is usually isolated as a stable, crystalline solid suitable for further synthetic use.

In medicinal chemistry, boronic acid derivatives such as this compound are important as enzyme inhibitors, particularly for proteases and other enzymes with nucleophilic active site residues. The boronic acid can form reversible covalent adducts with hydroxyl or amino groups in target proteins, while the pyridinyl carbamoyl moiety provides additional hydrogen-bonding interactions and electronic modulation to enhance binding affinity and selectivity. This combination of boron-centered reactivity and heterocyclic functionality enables the design of potent bioactive molecules.

Beyond pharmaceutical applications, [4-[(pyridin-2-yl)carbamoyl]phenyl]boronic acid is a versatile intermediate in organic synthesis. The boronic acid group participates in Suzuki–Miyaura cross-coupling to form biaryl compounds, while the amide linkage can be modified to produce diverse derivatives. This makes the molecule useful for constructing complex aromatic scaffolds, functionalized materials, and heterocyclic systems for chemical biology or material science applications.

Overall, [4-[(pyridin-2-yl)carbamoyl]phenyl]boronic acid is a multifunctional aromatic boronic acid featuring a pyridinyl carbamoyl substituent. Its combination of hydrogen-bonding, boron-centered reactivity, and electronic modulation makes it a valuable intermediate for organic synthesis, medicinal chemistry, and the preparation of bioactive or functionalized aromatic compounds.

References

2018. Acalabrutinib. Pharmaceutical Substances.
PubChem Literature ID: 906196375