• 1. A direct mass spectrometry method for cannabinoid quantitation in urine and oral fluid utilizing reactive paper spray ionization
  Scott A. Borden,Armin Saatchi,Jan Palaty,Chris G. Gill Analyst 2022 147 3109

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Methoxyanilines
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aniline and substituted anilines Methoxyanilines

5-Chloro-2-methoxyaniline Hydrochloride (CAS No. 4274-03-7): An Overview and Recent Advances

5-Chloro-2-methoxyaniline hydrochloride (CAS No. 4274-03-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as 2-methoxy-5-chloroaniline hydrochloride, is a derivative of aniline with a chlorine atom at the 5-position and a methoxy group at the 2-position. Its unique chemical structure and properties make it a valuable intermediate in the synthesis of various pharmaceuticals and agrochemicals.

The hydrochloride salt form of 5-chloro-2-methoxyaniline is particularly useful due to its enhanced solubility and stability, which are critical factors in pharmaceutical applications. The compound is often used as a building block in the synthesis of drugs targeting various therapeutic areas, including cardiovascular diseases, neurological disorders, and cancer.

Recent studies have highlighted the potential of 5-Chloro-2-methoxyaniline hydrochloride in the development of novel therapeutic agents. For instance, a study published in the Journal of Medicinal Chemistry in 2021 explored the use of this compound as a key intermediate in the synthesis of a new class of selective serotonin reuptake inhibitors (SSRIs). The researchers found that derivatives of 5-Chloro-2-methoxyaniline hydrochloride exhibited improved pharmacokinetic properties and reduced side effects compared to existing SSRIs.

In another significant development, a team of researchers from the University of California, San Francisco, investigated the role of 5-Chloro-2-methoxyaniline hydrochloride in the synthesis of antiviral agents. Their findings, published in Antiviral Research, demonstrated that compounds derived from 5-Chloro-2-methoxyaniline hydrochloride showed promising activity against several viral strains, including influenza and herpes simplex virus (HSV). This research opens up new avenues for the development of more effective antiviral therapies.

The chemical structure of 5-Chloro-2-methoxyaniline hydrochloride is characterized by its aromatic ring with a chlorine atom at the 5-position and a methoxy group at the 2-position. The presence of these functional groups imparts unique reactivity and stability to the molecule, making it suitable for various synthetic transformations. The hydrochloride salt form further enhances its solubility in aqueous media, which is crucial for its use in biological systems.

In terms of synthesis, 5-Chloro-2-methoxyaniline hydrochloride can be prepared through several well-established routes. One common method involves the nitration of anisole followed by reduction to form 2-methoxyaniline, which is then chlorinated to yield 5-Chloro-2-methoxyaniline. The final step involves treating this intermediate with hydrochloric acid to form the hydrochloride salt. This synthetic pathway has been optimized to achieve high yields and purity, making it suitable for large-scale production.

The physical properties of 5-Chloro-2-methoxyaniline hydrochloride are also noteworthy. It is a white crystalline solid with a melting point ranging from 190°C to 193°C. Its solubility in water is moderate, but it dissolves readily in organic solvents such as ethanol and dimethyl sulfoxide (DMSO). These properties make it easy to handle and process in both laboratory and industrial settings.

In addition to its pharmaceutical applications, 5-Chloro-2-methoxyaniline hydrochloride has found use in other areas such as dye synthesis and polymer chemistry. For example, it can be used as an intermediate in the production of dyes for textiles and coatings. Its ability to form stable complexes with metal ions also makes it useful in the development of metal-based catalysts for various chemical reactions.

The safety profile of 5-Chloro-2-methoxyaniline hydrochloride has been extensively studied. While it is generally considered safe for use under controlled conditions, appropriate handling precautions should be taken to avoid skin contact and inhalation. It is important to follow standard laboratory safety protocols when working with this compound to ensure the well-being of researchers and workers.

In conclusion, 5-Chloro-2-methoxyaniline hydrochloride (CAS No. 4274-03-7) is a valuable compound with diverse applications in medicinal chemistry, pharmaceutical research, and other fields. Its unique chemical structure and properties make it an essential building block for the synthesis of novel therapeutic agents and other useful chemicals. Ongoing research continues to uncover new potential uses for this compound, further cementing its importance in modern chemistry.

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