51771-21-2

Basic information

• Product Name: 4-methoxy-N-[(4-methoxyphenyl)methylideneamino]benzamide
• CAS NO: 51771-21-2
• Molecular Formula: C₁₆H₁₆N₂O₃
• Molecular Weight: 284.315
• Mol File: 51771-21-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 4-methoxy-N-[(4-methoxyphenyl)methylideneamino]benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-N-[(4-methoxyphenyl)methylideneamino]benzamide(51771-21-2)
• EPA Substance Registry System: 4-methoxy-N-[(4-methoxyphenyl)methylideneamino]benzamide(51771-21-2)

Safety Data

• Hazardous Substances Data: 51771-21-2(Hazardous Substances Data)

Upstream product

• 94-30-4 ethyl 4-methoxybenzoate 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 945538-59-0 2-(4'-methoxyphenyl)-5-(3''-methoxyphenyl)-2-acetyl-2,3-dihydro-1,3,4-oxadiazoline 
• 847-39-2 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole 

Relevant articles and documents

An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins

A glucose responsive insulin (GRI) that responds to changes in blood glucose concentrations has remained an elusive goal. Here we describe the development of glucose cleavable linkers based on hydrazone and thiazolidine structures. We developed linkers with low levels of spontaneous hydrolysis but increased level of hydrolysis with rising concentrations of glucose, which demonstrated their glucose responsiveness in vitro. Lipidated hydrazones and thiazolidines were conjugated to the LysB29 side-chain of HI by pH-controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated an unprecedented, chemically responsive linker concept for biopharmaceuticals.

An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent

Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.

Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

A convenient, efficient and one-pot synthesis of chemically and pharmaceutically interesting symmetrical-2,5-disubstituted-1,3,4-oxadiazoles is reported. The protocol involves anodic oxidation of aldehyde-N-arylhydrazones in anhyd. MeCN-LiClO4. Constant potential electrolysis carried out in an undivided cell and platinum electrodes leads to the formation of the corresponding oxadiazoles under ambient condition and the mechanism was deduced from voltammetry studies. The reaction proceeded smoothly with high atom economy. Springer Science+Business Media Dordrecht 2013.