4-Chlorophthalimide - 7147-90-2

4-Chlorophthalimide

Catalog Number: EVT-3161829
CAS Number: 7147-90-2
Molecular Formula: C8H4ClNO2
Molecular Weight: 181.57 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4-Chlorophthalimide, also known as 4-Chloro-1,2-benzenedicarboximide, is an organic compound with the molecular formula C8H4ClNO2. It belongs to the class of phthalimide derivatives and is widely used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and dyes. The compound exhibits interesting biological activity and has shown potential in different research areas.
Applications in Various Fields
In Medical Research, 4-Chlorophthalimide has been investigated for its role in drug development. It has shown promise as a lead compound for the development of novel antimicrobial agents, anti-inflammatory drugs, and anticancer therapies. Clinical trials are underway to evaluate the efficacy and safety of 4-Chlorophthalimide-based drugs in various disease conditions.
In Environmental Research, 4-Chlorophthalimide has been studied for its effects on ecosystems. It has been found to have toxic effects on aquatic organisms, highlighting the need for proper management and regulation of its use. Additionally, 4-Chlorophthalimide has been explored for its potential role in pollution management, particularly in the degradation of organic pollutants in contaminated environments.
In Industrial Research, 4-Chlorophthalimide has found applications in manufacturing processes. It is used as a key intermediate in the synthesis of agrochemicals, dyes, and other specialty chemicals. Its inclusion in manufacturing processes has been shown to improve product quality and efficiency. However, health and safety considerations must be taken into account to ensure the safe handling and disposal of 4-Chlorophthalimide.

Properties

CAS Number

7147-90-2

Product Name

4-Chlorophthalimide

IUPAC Name

5-chloroisoindole-1,3-dione

Molecular Formula

C8H4ClNO2

Molecular Weight

181.57 g/mol

InChI

InChI=1S/C8H4ClNO2/c9-4-1-2-5-6(3-4)8(12)10-7(5)11/h1-3H,(H,10,11,12)

InChI Key

BGJNRQSGJHVURK-UHFFFAOYSA-N

SMILES

C1=CC2=C(C=C1Cl)C(=O)NC2=O

Canonical SMILES

C1=CC2=C(C=C1Cl)C(=O)NC2=O
Method of Synthesis or Extraction
Several methods have been developed for the synthesis of 4-Chlorophthalimide. One commonly used method involves the reaction of phthalic anhydride with chlorine gas in the presence of a catalyst, such as aluminum chloride. This method offers a high yield of 4-Chlorophthalimide and is relatively efficient. However, it requires careful handling of chlorine gas, which poses safety and environmental concerns.
Another synthesis method involves the reaction of phthalic anhydride with thionyl chloride followed by treatment with ammonium hydroxide. This method also provides a good yield of 4-Chlorophthalimide and is considered safer than the chlorine gas method. However, it requires the use of thionyl chloride, which is a toxic and corrosive reagent.
Chemical Structure and Biological Activity
The chemical structure of 4-Chlorophthalimide consists of a chloro-substituted phthalimide moiety. This structural modification imparts unique properties to the compound, including enhanced biological activity. The mechanism of action of 4-Chlorophthalimide involves its interaction with specific biological targets, such as enzymes or receptors, leading to modulation of their activity.
Studies have shown that 4-Chlorophthalimide exhibits potent antimicrobial activity against various bacterial and fungal strains. It has also demonstrated anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines. Additionally, 4-Chlorophthalimide has shown promising anticancer activity by inducing apoptosis in cancer cells.
Biological Effects
The effects of 4-Chlorophthalimide on cell function and signal transduction pathways have been extensively studied. It has been found to interfere with cellular processes, such as DNA replication, protein synthesis, and cell cycle progression. Moreover, 4-Chlorophthalimide has been shown to modulate various signaling pathways involved in cell growth, differentiation, and survival.
While 4-Chlorophthalimide exhibits potential therapeutic effects, it is important to consider its potential toxic effects. Studies have indicated that high concentrations of 4-Chlorophthalimide can induce cytotoxicity and genotoxicity in certain cell types. Therefore, careful evaluation of its toxicity profile is necessary before considering its use in therapeutic applications.
Future Perspectives and Challenges
Despite the potential applications of 4-Chlorophthalimide, there are certain limitations in its use and study. The compound's stability, solubility, and bioavailability need to be further optimized to enhance its efficacy as a therapeutic agent. Additionally, more research is required to fully understand its mechanism of action and potential side effects.
Possible solutions and improvements include the development of novel synthesis methods that are more environmentally friendly and efficient. Furthermore, the identification of specific biological targets and elucidation of the molecular mechanisms underlying the biological activity of 4-Chlorophthalimide will contribute to its rational design and optimization.
Future trends and prospects in the application of 4-Chlorophthalimide in scientific research include the exploration of its potential in combination therapies, drug delivery systems, and targeted therapies. Additionally, the integration of computational approaches and high-throughput screening techniques will facilitate the discovery of new derivatives with improved bioactivity and reduced toxicity.
In conclusion, 4-Chlorophthalimide is a versatile compound with diverse applications in medical, environmental, and industrial research. Its synthesis methods, chemical structure, biological activity, and potential therapeutic and toxic effects have been discussed. Despite current limitations, future perspectives and challenges offer opportunities for further exploration and optimization of 4-Chlorophthalimide in scientific research.

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