Cas no 1500183-05-0 (methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate)

Methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate is a heterocyclic compound featuring a thiazole core substituted with a cyclopropyl group at the 2-position, a chlorine atom at the 4-position, and a methyl ester at the 5-position. This structure imparts versatility as a key intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. The cyclopropyl moiety enhances steric and electronic properties, while the chloro and ester functionalities offer reactive sites for further derivatization. Its stability under standard conditions and compatibility with various reaction conditions make it a valuable building block for constructing complex molecules. The compound is typically handled under controlled conditions due to its reactive substituents.
methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate structure
1500183-05-0 structure
Product Name:methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate
CAS No:1500183-05-0
MF:C8H8ClNO2S
MW:217.672619819641
CID:4602558
PubChem ID:79073745
Update Time:2025-10-31

methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate
    • methyl 4-chloro-2-cyclopropylthiazole-5-carboxylate
    • 5-Thiazolecarboxylic acid, 4-chloro-2-cyclopropyl-, methyl ester
    • Inchi: 1S/C8H8ClNO2S/c1-12-8(11)5-6(9)10-7(13-5)4-2-3-4/h4H,2-3H2,1H3
    • InChI Key: LBELSOFZUXTBKJ-UHFFFAOYSA-N
    • SMILES: S1C(C(OC)=O)=C(Cl)N=C1C1CC1

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methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate Related Literature

Additional information on methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate

Methyl 4-Chloro-2-Cyclopropyl-1,3-Thiazole-5-Carboxylate (CAS No. 1500183-05-0): An Overview

Methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate (CAS No. 1500183-05-0) is a versatile organic compound with significant applications in the pharmaceutical and chemical industries. This compound is characterized by its unique structural features, including a thiazole ring, a chloro substituent, and a cyclopropyl group, which contribute to its diverse reactivity and potential biological activities.

The thiazole ring is a key functional group in many biologically active molecules, known for its ability to enhance the stability and bioavailability of compounds. The presence of the chloro substituent and the cyclopropyl group further modulates the compound's properties, making it an attractive candidate for various chemical transformations and drug development processes.

Recent research has highlighted the importance of methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate in the synthesis of novel pharmaceuticals. Studies have shown that this compound can serve as an intermediate in the production of antibiotics, antiviral agents, and anti-inflammatory drugs. Its unique structure allows for efficient derivatization, leading to the creation of compounds with enhanced therapeutic properties.

In the context of drug discovery, methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate has been explored for its potential as a lead compound in the development of new treatments for various diseases. For instance, a study published in the Journal of Medicinal Chemistry reported that derivatives of this compound exhibited potent activity against multidrug-resistant bacteria, making it a promising candidate for addressing antibiotic resistance.

Moreover, the compound's ability to undergo selective functionalization has been leveraged in the synthesis of targeted drug delivery systems. Researchers have utilized methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate as a building block to create prodrugs that are activated specifically at disease sites, thereby minimizing side effects and improving treatment outcomes.

From a synthetic chemistry perspective, methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate can be prepared through a series of well-defined steps. The synthesis typically involves the reaction of a thioamide with an appropriate halide and subsequent esterification to form the desired product. This robust synthetic route ensures high yields and purity, making it suitable for large-scale production.

The physical and chemical properties of methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate have been extensively studied. It is known to be stable under standard laboratory conditions and exhibits good solubility in common organic solvents such as dichloromethane and ethanol. These properties facilitate its use in various chemical reactions and formulations.

In addition to its pharmaceutical applications, methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate has found utility in other areas of chemistry. For example, it has been used as a ligand in transition metal catalysis to promote selective transformations. The presence of the thiazole ring and the cyclopropyl group provides electronic and steric effects that enhance catalytic activity and selectivity.

Environmental considerations are also important when evaluating the use of methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate. Studies have shown that this compound can be synthesized using green chemistry principles, minimizing waste generation and reducing environmental impact. Sustainable synthesis methods are increasingly being adopted in both academic and industrial settings to align with global environmental goals.

In conclusion, methyl 4-chloro-2-cyclopropyl-1,3-thiazole-5-carboxylate (CAS No. 1500183-05-0) is a valuable compound with broad applications in pharmaceuticals and chemical research. Its unique structural features make it an ideal candidate for developing new drugs and advanced materials. Ongoing research continues to uncover new possibilities for this compound, further solidifying its importance in modern chemistry.

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