3815-86-9

Usage

Uses

Used in Polymer Chemistry:
Malonic dihydrazide is used as a crosslinking agent for enhancing the properties of polymers, such as their stability and mechanical strength.
Used in Chelation Therapy:
Malonic dihydrazide is used as a chelating agent for the treatment of heavy metal poisoning, as it can form stable complexes with metal ions, aiding in their removal from the body.
Used in Metal Ion Sensing:
Malonic dihydrazide is used as a sensing agent for detecting and quantifying metal ions in various environments, due to its ability to form stable complexes with these ions.
Used in Pharmaceutical Synthesis:
Malonic dihydrazide is used as a precursor in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Synthesis:
Malonic dihydrazide is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, to improve crop protection and yield.
Used in Organic Synthesis and Materials Science:
Malonic dihydrazide is used as a versatile building block in organic synthesis and materials science, enabling the creation of new compounds and materials with unique properties.

InChI:InChI=1/C3H8N4O2/c4-6-2(8)1-3(9)7-5/h1,4-5H2,(H,6,8)(H,7,9)

Upstream product

• 64-17-5 ethanol 
• 105-53-3 diethyl malonate 
• 31575-84-5 (1-hydroxyethylidene)malonic acid diethyl ester 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 570-08-1 diethyl acetylmalonate 

Downstream Products

• 92514-62-0 malonic acid bis-(2-chloro-benzylidenehydrazide) 
• 29816-49-7 malonic acid bis-(4-nitro-benzylidenehydrazide) 
• 29816-43-1 Malonic acid di-2-benzalhydrazide 
• 92514-61-9 malon-di-<(p-hydroxy)benzylidene amino>amide 
• 73692-65-6 malonic acid bis-(4-methoxy-benzylidenehydrazide) 
• 73692-60-1 malonic acid bis-(3-chloro-benzylidenehydrazide) 
• 29816-50-0 malonic acid bis-cinnamylidenehydrazide 
• 29816-51-1 acetophenone malonoyldihydrazone 
• 30222-55-0 C₁₅H₁₄Cl₂N₄O₆S₂ 
• 30222-68-5 C₂₃H₂₄N₄O₂ 
• 4744-71-2 pyrazolidine‐3,5‐dione 
• 83388-69-6 2,5-Bis(2-phenylamino-phenyl)-1,3,4-thiadiazol 
• 139004-27-6 4,4'-Di(2,3-dimethylphenyl)bis-malonylthiosemicarbazide 
• 132500-84-6 N,N'-bis(4-anisoyl)malonic acid dihydrazide 

Relevant academic research and scientific papers

The reaction of ethyl 2-oxo-2H-chromene-3-carboxylate with hydrazine hydrate

Although salicylaldehyde azine (3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2H-chromene-3-carboxylate (1) with hydrazine hydrate, we identified another main reaction product, besides 3, which was identified as malono-hydrazide (4). In the last two decades, however, some articles have claimed that this reaction afforded exclusively hydrazide 2 and they have reported the use of this hydrazide 2 as a precursor in the syntheses of several heterocyclic compounds and hydrazones 6. We reported herein a study of the formation of 2 and a facile route for the synthesis of the target compounds N'-arylidene-2-oxo-2H-chromene-3-carbohydrazides 6a-f.

Synthesis and crystal structure of some 3,5-pyrazolidinediones

Syntheses of various derivatives of 3,5-pyrazolidenedione are reported. This includes 4-arylidene (alkylidene or aralkylidene)-3,5-pyrazolidinediones, which on epoxidation gave unreported oxiranes. The syntheses of these derivatives were based on either the Knoevenagel reaction of carbonyl derivatives with 3,4-pyrazolidinedione or cyclization of arylidene (alkylidene) malonic acid hydrazide with glacial acetic acid. 4-Arylazo-3,5-pyrazolidinedione derivatives were also prepared by coupling of aryldiazonium salts with 3,5-pyrazolidinedione or cyclization of arylazomalonic acid hydrazide. Reduction of 4-benzylidene derivatives gave the corresponding benzyl derivatives. The structure of the new products was confirmed by elemental and spectral analyses and X-ray crystallography.

Efficient synthesis of 4-ethoxycarbonyl pyrazolin-5-one derivatives

Concise and efficient methods for the preparation of 3-substituted 4-ethoxycarbonylpyrazolin-5-ones are described. The synthetic strategies involve carbon-acylation in the presence of base, followed by ring cyclization with hydrazine or hydrazine monohydrochloride.

Synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones

The synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones from acylated ethyl acetoacetates and diethyl malonates is described. The reaction of acylated ethyl acetoacetates and diethyl acetylmalonate with hydrazine (98%) gave 3-substituted pyrazolin-5-ones and malonyldihydrazide, respectively, following a deacetylation-condensation sequence. The reaction of ethyl 2-acetyl-3-hydroxy-2-butenoate and diethyl 2-(1-hydroxyethylidene)malonate with hydrazine monohydrochloride yielded ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate and 4-ethoxycarbonyl-3-methylpyrazolin-5-one, respectively, following a dehydration-cyclocondensation sequence, in high yields.