2,4-Dichloro-5,7-dihydrothieno[3,4-D]pyrimidine
[CAS# 74901-71-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 2,4-Dichloro-5,7-dihydrothieno[3,4-D]pyrimidine
• Molecular Formula: C₆H₄Cl₂N₂S
• Molecular Weight: 207.08
• CAS Registry Number: 74901-71-6
• EC Number: 888-929-5
• SMILES: C1C2=C(CS1)N=C(N=C2Cl)Cl

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.670, Calc.^*
• Boiling Point: 371.7±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 178.6±27.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2,4-Dichloro-5,7-dihydrothieno[3,4-D]pyrimidine is a heterocyclic compound characterized by a fused pyrimidine and thiophene ring structure. This compound has gained attention in various fields due to its unique properties and potential applications, particularly in the realm of medicinal chemistry.

The discovery of 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine can be traced back to research aimed at synthesizing new classes of bioactive compounds. The development of this compound is part of the ongoing exploration of thiophene-containing heterocycles, which have been recognized for their diverse biological activities. The structural features of 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine contribute to its potential as a lead compound for drug development.

The compound's synthesis typically involves cyclization reactions of suitable precursors, leading to the formation of the thieno[3,4-D]pyrimidine framework. Various synthetic strategies have been developed to optimize yield and purity, reflecting the compound's importance in research.

One of the most significant applications of 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine lies in its pharmacological properties. Research has shown that this compound exhibits various biological activities, including antimicrobial, antiviral, and anti-inflammatory effects. These attributes make it a candidate for further investigation as a potential therapeutic agent. In particular, its antiviral properties have been explored in the context of developing treatments for viral infections, as it may inhibit the replication of certain viruses.

Furthermore, studies have indicated that derivatives of 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine may demonstrate selective inhibition of specific enzymes, such as kinases, which are crucial targets in cancer therapy. This suggests that modifications to its structure could lead to novel anticancer agents.

The compound has also been evaluated in the field of agrochemicals. Its potential as a pesticide or herbicide is of particular interest due to its ability to inhibit specific biological pathways in pests and weeds. This application is supported by its chemical stability and efficacy in various formulations, which are essential characteristics for agricultural use.

In addition to its medicinal and agricultural applications, 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine serves as a valuable intermediate in organic synthesis. Its unique structure allows for further modifications, enabling the development of new compounds with tailored properties. Researchers are actively exploring its potential as a building block for creating complex molecular architectures that can be utilized in various chemical domains.

Ongoing research aims to deepen the understanding of the biological mechanisms underlying the activity of 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine, with a focus on elucidating its interactions at the molecular level. Investigating its structure-activity relationships is essential for optimizing its efficacy and safety profile in potential therapeutic applications.

In summary, 2,4-dichloro-5,7-dihydrothieno[3,4-D]pyrimidine is a compound of significant interest due to its diverse biological activities and potential applications in medicine and agriculture. Its discovery reflects the broader effort to explore the pharmacological potential of thiophene-containing heterocycles, making it a promising candidate for future research and development.

References

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