For chemists engaged in organic synthesis, understanding the fundamental properties and synthesis pathways of key intermediates is critical for successful project execution. 4-Amino-2-bromopyridine (CAS 7598-35-8) is a prime example of such a compound, offering a unique combination of functional groups that make it invaluable in a multitude of synthetic strategies.

Understanding the Molecular Structure and Properties

4-Amino-2-bromopyridine, with the chemical formula C5H5BrN2 and a molecular weight of 173.01 g/mol, is a substituted pyridine. Its structure features:

  • A Pyridine Ring: A six-membered aromatic heterocycle containing one nitrogen atom, which influences its electronic properties and reactivity.
  • An Amino Group (-NH2) at position 4: This group can act as a nucleophile, a base, or participate in various derivatization reactions like acylation or alkylation. It also affects the electron density of the pyridine ring.
  • A Bromine Atom (-Br) at position 2: This halogen atom is an excellent leaving group and a versatile handle for carbon-carbon and carbon-heteroatom bond formation via transition metal-catalyzed cross-coupling reactions (e.g., Suzuki, Stille, Heck, Buchwald-Hartwig couplings).

Physically, it typically appears as an off-white to white powder, with a melting point ranging from 92-96°C. Its solubility is generally good in common organic solvents such as ethanol, ethyl acetate, and DMSO, but limited in water.

Synthesis Routes for 4-Amino-2-bromopyridine

The synthesis of 4-Amino-2-bromopyridine commonly involves the reduction of a nitro group on a pre-existing brominated pyridine derivative. A standard method starts with 2-bromo-4-nitropyridine. The nitro group can be reduced to an amino group using various reducing agents. Common reduction systems include:

  • Metal and Acid: For instance, iron powder in acetic acid is a frequently employed method. This reaction typically requires elevated temperatures and careful pH adjustment during workup to liberate the free amine from its salt form.
  • Catalytic Hydrogenation: Using hydrogen gas in the presence of a catalyst like palladium on carbon (Pd/C) can also effectively reduce the nitro group.
  • Other Reductions: Reagents like tin(II) chloride (SnCl2) or sodium hydrosulfite can also be utilized depending on the specific reaction conditions and desired purity.

The choice of synthesis method often depends on factors such as cost of reagents, scalability, yield, purity requirements, and environmental considerations. Manufacturers like NINGBO INNO PHARMCHEM CO.,LTD. optimize these processes to ensure consistent supply of high-quality 4-Amino-2-bromopyridine.

Applications and Sourcing for Researchers and Manufacturers

This intermediate is crucial for building complex molecules in pharmaceutical drug discovery, agrochemical development, and materials science. For those looking to buy 4-Amino-2-bromopyridine, sourcing from reputable manufacturers is key to guarantee purity and reliability. Understanding its chemical properties aids in designing efficient synthetic routes and troubleshooting potential issues. We, at NINGBO INNO PHARMCHEM CO.,LTD., are dedicated to providing this essential intermediate with the high purity and consistent quality that researchers and manufacturers require to drive innovation forward.