structure of 2-Chloro-6-isopropylpyridine-3-boronic acid

2-Chloro-6-isopropylpyridine-3-boronic acid

CAS No.: 1003043-37-5
M. Wt: 199.44200
M. Fa: C8H11BClNO2
InChI Key: FBLHWIQSYHMHSK-UHFFFAOYSA-N
Appearance: White To Yellow Solid

Names and Identifiers of 1003043-37-5

CAS Number

1003043-37-5

MDL Number

MFCD08274472

IUPAC Name

(2-chloro-6-propan-2-ylpyridin-3-yl)boronic acid

InChI

InChI=1S/C8H11BClNO2/c1-5(2)7-4-3-6(9(12)13)8(10)11-7/h3-5,12-13H,1-2H3

InChIKey

FBLHWIQSYHMHSK-UHFFFAOYSA-N

Canonical SMILES

B(C1=C(N=C(C=C1)C(C)C)Cl)(O)O

UNSPSC Code

12352100

Physical and chemical properties of 1003043-37-5

Exact Mass

199.05700

LogP

0.53820

Molecular Formula

C8H11BClNO2

Molecular Weight

199.44200

PSA

53.35000

Safety Information of 1003043-37-5

Pictograms

Signal Word

Warning

Safety Data Sheet

Supports customized editing of SDS information and downloading in PDF documents.

Applications of 1003043-37-5

2-Chloro-6-isopropylpyridine-3-boronic acid finds applications in various fields:

  • Pharmaceutical intermediates: It serves as a building block in the synthesis of complex drug molecules, particularly those containing functionalized pyridine rings.
  • Agrochemicals: The compound can be used in the development of novel pesticides and herbicides.
  • Materials science: It may be employed in the synthesis of advanced materials, such as organic semiconductors or ligands for metal-organic frameworks.

Interaction Studies of 1003043-37-5

Interaction studies involving 2-Chloro-6-isopropylpyridine-3-boronic acid may focus on:

  • Hydrogen bonding: The boronic acid group can form hydrogen bonds with various biological targets or other molecules.
  • Metal complexation: The pyridine nitrogen and boronic acid oxygen atoms can coordinate with metal ions, forming stable complexes.
  • Protein binding: Potential interactions with specific protein targets, such as enzymes or receptors, may be investigated for drug discovery purposes.
Similar Compounds

Several compounds share structural similarities with 2-Chloro-6-isopropylpyridine-3-boronic acid:

  • 3-Pyridineboronic acid: A simpler analog lacking the chloro and isopropyl substituents.
  • 2-Chloropyridine-3-boronic acid: Similar structure without the isopropyl group.
  • 2-Chloro-6-methylpyridine-3-boronic acid: Contains a methyl group instead of an isopropyl group.
  • 2-Fluoro-6-isopropylpyridine-3-boronic acid: Fluorine replaces chlorine at position 2.
  • 2-Chloro-4-isopropylpyridine-3-boronic acid: Isopropyl group at position 4 instead of 6.

The uniqueness of 2-Chloro-6-isopropylpyridine-3-boronic acid lies in its specific substitution pattern, combining the reactivity of boronic acids with the electronic properties of chloropyridines and the steric effects of the isopropyl group. This combination allows for selective transformations and tailored reactivity in various synthetic applications.

Biological Activity of 1003043-37-5

While specific biological activities of 2-Chloro-6-isopropylpyridine-3-boronic acid are not extensively reported, boronic acids, in general, have shown potential in various biological applications:

  • Enzyme inhibition: Boronic acids can form reversible covalent bonds with active site residues of certain enzymes, making them potential inhibitors.
  • Antibacterial properties: Some boronic acid derivatives exhibit antibacterial activity by interfering with bacterial cell wall synthesis.
  • Potential anticancer activity: Boronic acid-containing compounds have been explored as proteasome inhibitors and kinase inhibitors in cancer research.

Physical sample testing spectrum (NMR) of 1003043-37-5

Physical sample testing spectrum (NMR) of 1003043-37-5