2-Amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene
[CAS# 50508-66-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 2-Amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene
• Synonyms: [2-Amino-4,5-di(methyl)thiophen-3-yl](4-chlorophenyl)methanone
• Molecular Formula: C₁₃H₁₂ClNOS
• Molecular Weight: 265.76
• CAS Registry Number: 50508-66-2
• SMILES: CC1=C(SC(=C1C(=O)C2=CC=C(C=C2)Cl)N)C

Properties

• Solubility: Insoluble (7.2E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.303±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.638, Calc.^*
• Boiling Point: 435.4±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 217.1±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

2-Amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene is a chemical compound that combines a thiophene ring with both an amino group and a 4-chlorobenzoyl group, making it an interesting structure for synthetic and pharmaceutical chemistry. Thiophenes are aromatic heterocycles known for their presence in various biologically active molecules and organic materials. The incorporation of functional groups such as an amino group and a benzoyl moiety further enhances the compound's reactivity and potential for applications in drug development and materials science.

The discovery of thiophene derivatives, including 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene, can be traced back to the 19th century, when thiophene was first isolated from coal tar. Over time, chemists have developed numerous methods to functionalize the thiophene ring, incorporating a wide range of substituents to tailor its chemical properties for specific applications. In the case of 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene, the amino group and 4-chlorobenzoyl substituent are key features that contribute to its biological and chemical activity.

One of the primary applications of 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene is in the field of medicinal chemistry. The presence of both an amino group and a benzoyl group makes the compound a promising candidate for developing bioactive molecules, particularly those with antimicrobial, anti-inflammatory, or anticancer properties. Many thiophene derivatives have shown activity against various biological targets, and the ability to modify the functional groups attached to the ring structure allows for further optimization of their pharmacological properties. The chlorobenzoyl group can potentially enhance the compound's ability to interact with specific receptors or enzymes, making it an attractive target for drug discovery.

In addition to its medicinal applications, 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene can also be used as an intermediate in organic synthesis. The amino group is a versatile functional group, often employed in the creation of more complex molecules, including those used in materials science, polymers, and agrochemicals. Furthermore, the thiophene ring itself is a useful scaffold in the design of organic semiconductors and conductive materials. The ability to modify the structure by introducing different substituents allows for the creation of materials with tailored electronic properties, which could be beneficial for applications in optoelectronics and organic photovoltaics.

The reactivity of the 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene compound also makes it valuable in the field of catalysis. Thiophene derivatives are often used as ligands in transition metal catalysis due to their ability to coordinate with metal centers and participate in a variety of reactions, including cross-coupling reactions, polymerization, and other processes in synthetic chemistry. This compound, with its unique combination of functional groups, could be utilized as a catalyst or a precursor to more complex catalytic systems in organic reactions.

In summary, 2-amino-3-(4-chlorobenzoyl)-4,5-dimethylthiophene is a versatile and reactive compound with significant potential in medicinal chemistry, organic synthesis, and materials science. Its combination of functional groups, including the amino and chlorobenzoyl moieties, opens up a wide range of applications, from drug development to the creation of novel materials. As research continues to explore the properties and reactivity of thiophene derivatives, this compound could play a key role in the development of new therapeutic agents and advanced materials.