Cas no 1381936-86-2 (4-Amino-2-chloro-3-phenylpyridine)

4-Amino-2-chloro-3-phenylpyridine is a heterocyclic organic compound featuring a pyridine core substituted with an amino group at the 4-position, a chlorine atom at the 2-position, and a phenyl ring at the 3-position. This structure imparts versatility as a key intermediate in pharmaceutical and agrochemical synthesis. The amino and chloro functional groups enhance reactivity, enabling selective modifications for the development of bioactive molecules. Its phenyl substitution contributes to increased lipophilicity, improving compatibility in organic synthesis. The compound is particularly valuable in medicinal chemistry for constructing nitrogen-containing scaffolds. High purity grades ensure consistent performance in research and industrial applications.
4-Amino-2-chloro-3-phenylpyridine structure
1381936-86-2 structure
Product Name:4-Amino-2-chloro-3-phenylpyridine
CAS No:1381936-86-2
MF:C11H9ClN2
MW:204.655561208725
CID:4899133
Update Time:2025-05-19

4-Amino-2-chloro-3-phenylpyridine Chemical and Physical Properties

Names and Identifiers

    • 4-Amino-2-chloro-3-phenylpyridine
    • Inchi: 1S/C11H9ClN2/c12-11-10(9(13)6-7-14-11)8-4-2-1-3-5-8/h1-7H,(H2,13,14)
    • InChI Key: YYWCCKJSYOJOJC-UHFFFAOYSA-N
    • SMILES: ClC1C(=C(C=CN=1)N)C1C=CC=CC=1

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 180
  • XLogP3: 2.8
  • Topological Polar Surface Area: 38.9

4-Amino-2-chloro-3-phenylpyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A029015757-250mg
4-Amino-2-chloro-3-phenylpyridine
1381936-86-2 95%
250mg
$960.40 2022-04-02
Alichem
A029015757-1g
4-Amino-2-chloro-3-phenylpyridine
1381936-86-2 95%
1g
$2,808.15 2022-04-02

Additional information on 4-Amino-2-chloro-3-phenylpyridine

Introduction to 4-Amino-2-chloro-3-phenylpyridine (CAS No. 1381936-86-2)

4-Amino-2-chloro-3-phenylpyridine, identified by its Chemical Abstracts Service (CAS) number 1381936-86-2, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. This heterocyclic aromatic amine has garnered attention due to its structural versatility and potential applications in the development of novel therapeutic agents. The compound's unique framework, featuring a pyridine core substituted with an amino group, a chloro group, and a phenyl ring, positions it as a valuable intermediate in synthetic chemistry and drug discovery.

The structural attributes of 4-Amino-2-chloro-3-phenylpyridine make it a compelling candidate for further exploration in medicinal chemistry. The presence of both electron-donating and electron-withdrawing groups on the pyridine ring influences its reactivity and binding properties, which are critical factors in drug design. Specifically, the amino group enhances nucleophilic substitution reactions, while the chloro substituent can participate in various coupling reactions, such as Suzuki or Buchwald-Hartwig couplings. These characteristics allow chemists to modify the compound's structure systematically, leading to the synthesis of diverse derivatives with tailored pharmacological profiles.

In recent years, there has been growing interest in exploring the pharmacological potential of pyridine derivatives. Studies have demonstrated that compounds incorporating the pyridine scaffold exhibit a wide range of biological activities, including antimicrobial, anti-inflammatory, and anticancer effects. Among these derivatives, 4-Amino-2-chloro-3-phenylpyridine has shown promise as a precursor for molecules targeting specific disease pathways. For instance, researchers have investigated its role in developing inhibitors for kinases and other enzymes involved in cancer progression.

One of the most notable areas of research involving 4-Amino-2-chloro-3-phenylpyridine is its application in oncology. The compound's ability to interact with biological targets such as tyrosine kinases has been exploited to create novel anticancer agents. Preclinical studies have indicated that derivatives of this compound can disrupt signaling pathways essential for tumor growth and survival. While further research is needed to fully elucidate their therapeutic efficacy and safety profiles, these findings underscore the compound's potential as a lead molecule in oncology drug development.

Additionally, 4-Amino-2-chloro-3-phenylpyridine has been explored for its antimicrobial properties. The combination of an amino group and a phenyl ring creates a favorable environment for disrupting bacterial cell wall synthesis or inhibiting key metabolic enzymes. Preliminary studies have shown that certain derivatives exhibit activity against Gram-positive bacteria, making them attractive candidates for developing new antibiotics to combat antibiotic-resistant strains.

The synthesis of 4-Amino-2-chloro-3-phenylpyridine involves multi-step organic reactions that highlight the compound's synthetic utility. One common synthetic route involves the chlorination of an appropriately substituted pyridine derivative followed by nucleophilic substitution with an amine source. Alternatively, palladium-catalyzed cross-coupling reactions can be employed to introduce the phenyl ring onto a halogenated pyridine precursor. These synthetic strategies not only demonstrate the versatility of 4-Amino-2-chloro-3-phenylpyridine as a building block but also provide valuable insights into optimizing reaction conditions for high yields and purity.

The pharmaceutical industry continues to leverage advanced computational methods to accelerate drug discovery processes involving compounds like 4-Amino-2-chloro-3-phenylpyridine. Molecular docking simulations and virtual screening techniques enable researchers to predict binding interactions between the compound and target proteins with high accuracy. These computational approaches complement traditional experimental methods by identifying promising candidates for further validation, thereby reducing the time and cost associated with drug development.

In conclusion, 4-Amino-2-chloro-3-phenylpyridine (CAS No. 1381936-86-2) represents a structurally intriguing and biologically relevant compound with significant potential in pharmaceutical research. Its unique combination of functional groups makes it a versatile intermediate for synthesizing novel therapeutic agents targeting various diseases, particularly cancer and infectious disorders. As research progresses, further exploration of this compound's pharmacological properties will likely yield valuable insights into developing next-generation drugs with improved efficacy and reduced side effects.

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