Ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate
[CAS# 473927-63-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: Ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate
• Synonyms: Ethyl (2cis)-chloro[(4-methoxyphenyl)hydrazono]acetate; (2Z)-2-Chloro-2-[2-(4-methoxyphenyl)hydrazinylidene]acetic acid ethyl ester
• Molecular Formula: C₁₁H₁₃ClN₂O₃
• Molecular Weight: 256.69
• CAS Registry Number: 473927-63-8
• EC Number: 696-101-8
• SMILES: CCOC(=O)C(=NNC1=CC=C(C=C1)OC)Cl

Properties

• Density: 1.23

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

Ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate is a derivative of hydrazones, a class of compounds known for their versatile applications in organic synthesis and drug discovery. The structure of this compound features an ethyl ester, a chloro group, and a hydrazono moiety connected to a 4-methoxyphenyl group. Its Z-configuration refers to the positioning of the substituents around the hydrazono group, contributing to its chemical behavior in various reactions.

The discovery of ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate stems from advances in hydrazone chemistry, which became significant during the 20th century as researchers explored the reactivity of these compounds in different condensation reactions. The synthesis typically involves the condensation of ethyl chloroacetate with a 4-methoxyphenylhydrazine derivative. Hydrazones, including this compound, are particularly useful as intermediates in organic synthesis due to their ability to form a variety of heterocyclic compounds.

One of the notable applications of ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate is its use in the synthesis of nitrogen-containing heterocycles. These heterocyclic compounds are of significant interest in medicinal chemistry, as many exhibit bioactive properties such as antimicrobial, anticancer, and antiviral activities. The presence of the hydrazono group facilitates cyclization reactions, which can lead to the formation of five- or six-membered rings with potential biological activity. The compound also plays a role in the synthesis of azo compounds and other hydrazone derivatives used in dyes, pigments, and pharmaceuticals.

In addition to its utility in synthesis, ethyl (2Z)-chloro[(4-methoxyphenyl)hydrazono]acetate has potential applications in materials science, where hydrazone derivatives are used in the development of functional materials such as sensors and molecular switches. The reversible nature of the hydrazone linkage makes these compounds ideal candidates for stimuli-responsive materials. Further research continues to explore the full range of applications of this compound, particularly in fields that benefit from its reactivity and functional versatility.

References

2019. Analytical Quality by Design Approach for a Stability-Indicating Method to Determine Apixaban and Its Related Impurities. Chromatographia, 82(11).
DOI: 10.1007/s10337-019-03815-9

2008. Synthesis and molecular structure of [2,3,4,5-tetrafluoro-6-(p-methoxyphenylamino)phenyl]diphenylphosphine. Russian Journal of General Chemistry, 78(6).
DOI: 10.1134/s1070363208060121