80214-09-1

Basic information

• Product Name: ethyl 2-(4-methoxybenzylidene)hydrazinecarboxylate
• CAS NO: 80214-09-1
• Molecular Formula: C₁₁H₁₄N₂O₃
• Molecular Weight: 222.2405
• Mol File: 80214-09-1.mol
• Article Data: 3

Chemical Properties

• Density: 1.11g/cm³
• Refractive Index: 1.515
• CAS DataBase Reference: ethyl 2-(4-methoxybenzylidene)hydrazinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(4-methoxybenzylidene)hydrazinecarboxylate(80214-09-1)
• EPA Substance Registry System: ethyl 2-(4-methoxybenzylidene)hydrazinecarboxylate(80214-09-1)

Safety Data

• Hazardous Substances Data: 80214-09-1(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 4114-31-2 ethylhydrazine carboxylate 

Downstream Products

• 1185741-59-6 dimethyl 2-cyclohexyliminomethylene-3-[N-ethoxycarbonyl-N'-(4-methoxybenzylidene)hydrazino]succinate 
• 1210608-84-6 dimethyl 2-(2'-(4-methylbenzylidene)-1-(ethoxycarbonyl)hydrazino)-3-(triphenylphosphanylidene)succinate 

Relevant articles and documents

From solution to in-cell study of the chemical reactivity of acid sensitive functional groups: A rational approach towards improved cleavable linkers for biospecific endosomal release

pH-Sensitive linkers designed to undergo selective hydrolysis at acidic pH compared to physiological pH can be used for the selective release of therapeutics at their site of action. In this paper, the hydrolytic cleavage of a wide variety of molecular structures that have been reported for their use in pH-sensitive delivery systems was examined. A wide variety of hydrolytic stability profiles were found among the panel of tested chemical functionalities. Even within a structural family, a slight modification of the substitution pattern has an unsuspected outcome on the hydrolysis stability. This work led us to establish a first classification of these groups based on their reactivities at pH 5.5 and their relative hydrolysis at pH 5.5 vs. pH 7.4. From this classification, four representative chemical functions were selected and studied in-vitro. The results revealed that only the most reactive functions underwent significant lysosomal cleavage, according to flow cytometry measurements. These last results question the acid-based mechanism of action of known drug release systems and advocate for the importance of an in-depth structure-reactivity study, using a tailored methodology, for the rational design and development of bio-responsive linkers.

Acetylenic Ketones. 8. Synthesis and Spectroscopic Studies of Some Hydrazones

Aroylphenylacetylenes, benzaldehydes, and acetophenones reacted with ethyl and phenyl hydrazinecarboxylates to give the corresponding hydrazone N-carboxylic esters of ω-aroylacetophenone (IIIa-f), benzaldehyde (IXa-f), and acetophenone (IXg-l).UV, IR, and