Ethyl chloro[(4-methoxyphenyl)hydrazono]acetate
[CAS# 27143-07-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: Ethyl chloro[(4-methoxyphenyl)hydrazono]acetate
• Synonyms: Chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester
• Molecular Formula: C₁₁H₁₃ClN₂O₃
• Molecular Weight: 256.69
• CAS Registry Number: 27143-07-3
• EC Number: 608-053-7
• SMILES: CCOC(=O)/C(=N/NC1=CC=C(C=C1)OC)/Cl

Properties

• Density: 1.23
• Melting point: 94 °C

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

Discovery and Applications

Ethyl chloro[(4-methoxyphenyl)hydrazinyl]acetate is a compound belonging to the class of hydrazones, known for its reactivity and wide range of applications in organic synthesis. The structure of the compound consists of an ester group (ethyl acetate), a chlorine group attached to the central carbon, and a hydrazone portion formed with 4-methoxyphenylhydrazine. The introduction of the hydrazine group enhances the reactivity of the molecule, especially in coupling and condensation reactions.

The discovery of compounds such as ethyl chloro[(4-methoxyphenyl)hydrazinyl]acetate can be traced back to the development of hydrazone chemistry in the early 20th century, which highlights their importance in synthetic organic chemistry. Hydrazones are usually synthesized by condensation of hydrazine derivatives with carbonyl compounds, and ethyl chloro[(4-methoxyphenyl)hydrazinyl]acetate is no exception. The compound is produced by the reaction of 4-methoxyphenylhydrazine with ethyl chloroacetate under controlled conditions.

One of the major applications of ethyl chloro[(4-methoxyphenyl)hydrazinyl]acetate is as an intermediate in the synthesis of heterocyclic compounds. These heterocyclic compounds have a variety of chemical and biological properties and are of great value in pharmaceuticals, agrochemicals, and materials science. The hydrazone functionality in this compound enables it to participate in various cyclization reactions to form nitrogen-containing heterocycles with biological activities such as antibacterial, antiviral or anticancer properties.

In medicinal chemistry, hydrazone compounds have been explored for their potential as enzyme inhibitors or building blocks for drug design. Ethyl chloro[(4-methoxyphenyl)hydrazinyl]acetate is a valuable intermediate for the synthesis of such bioactive compounds, especially when further modified to introduce different functional groups or heterocyclic cores. In addition, hydrazones are useful in analytical chemistry due to their ability to form complexes with metal ions, which makes them suitable for the detection and quantification of metals in environmental and clinical samples.

References

2023. A practical synthesis for the key intermediate of apixaban. Monatshefte für Chemie - Chemical Monthly, 154(12).
DOI: 10.1007/s00706-023-03143-7

2012. Ethyl (Z)-2-chloro-2-[2-(4-methoxyphenyl)hydrazin-1-ylidene]acetate. Acta Crystallographica Section E: Structure Reports Online, 68(12).
DOI: 10.1107/s1600536812044285

2007. The reaction of N-R-2-cyanothioacetamides with ethyl[(aryl)hydrazono]chloroacetates. Chemistry of Heterocyclic Compounds, 43(1).
DOI: 10.1007/s10593-007-0014-0