928-73-4

Basic information

• Product Name: [(aminocarbonyl)hydrazono]acetic acid
• Synonyms: [(aminocarbonyl)hydrazono]acetic acid;Glyoxylicacidsemicarbazone-discontinued;IPO3884;Semicarbazonoacetic acid;Ccris 2717;Einecs 213-182-3
• CAS NO: 928-73-4
• Molecular Formula: C₃H₅N₃O₃
• Molecular Weight: 131.0901
• EINECS: 213-182-3
• Mol File: 928-73-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 258 °C (decomp)
• Appearance: /
• Density: 1.66g/cm³
• Refractive Index: 1.601
• PKA: 13.90±0.46(Predicted)
• CAS DataBase Reference: [(aminocarbonyl)hydrazono]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(aminocarbonyl)hydrazono]acetic acid(928-73-4)
• EPA Substance Registry System: [(aminocarbonyl)hydrazono]acetic acid(928-73-4)

Safety Data

• Hazardous Substances Data: 928-73-4(Hazardous Substances Data)

Usage

General Description

[(Aminocarbonyl)hydrazono]acetic acid, also known as 2-[[(diaminomethylidene)amino]oxy]acetic acid, is a chemical compound with the molecular formula C3H7N3O3. It is an organic compound containing a hydrazine group and a carboxylic acid group, making it an important building block for the synthesis of various pharmaceuticals and agrochemicals. [(aminocarbonyl)hydrazono]acetic acid is used as a reagent in the preparation of hydrazone derivatives, which have applications in medicinal chemistry and drug development. Additionally, [(aminocarbonyl)hydrazono]acetic acid has been studied for its potential use as an anti-tumor agent due to its ability to inhibit the growth of cancer cells. Its versatile chemical structure and potential biological activities make it an important compound in the field of medicinal chemistry and pharmaceutical research.

InChI:InChI=1/C3H5N3O3/c4-3(9)6-5-1-2(7)8/h1H,(H,7,8)(H3,4,6,9)

Upstream product

• 79-43-6 dichloro-acetic acid 
• 4426-72-6 hydrazine carboxamide 
• 298-12-4 Glyoxilic acid 
• 563-41-7 semicarbazide hydrochloride 
• 75-87-6 chloral 
• 302-17-0 chloral hydrate 

Downstream Products

• 80305-79-9 glyoxylic acid 2-(4-chlorobenzyl)semicarbazone 
• 100-52-7 benzaldehyde 
• 80305-80-2 C₁₀H₁₀ClN₃O₃ 
• 74-90-8 hydrogen cyanide 
• 64-19-7 acetic acid 
• 80305-81-3 C₁₀H₉Cl₂N₃O₃ 
• 80305-82-4 C₁₀H₉Cl₂N₃O₃ 
• 461-89-2 6-azauracil 

Relevant articles and documents

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity

A new group of 3-substituted-5H-benzo[5,6][1,4]thiazino[3,2-e][1,2,4]triazines was designed, synthesized and evaluated as inhibitors of 15-lipoxygenase (15-LO), and the results were compared with those of standard ligand 4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine (4-MMPB). Among the newly designed ligands, compound 9e showed the best IC50 of 15-LO inhibition (IC50?=?38?μM). The docking calculations were performed in MOE software based on the function of force-field scoring, in order to study the interaction of these new compounds and standard ligand with 15-LO. The docking study implied that these ligands have hydrogen bond interaction with the residue of active site of 15-LO.

Preparation of α-(2,2-diphenylhydrazino)lactones and related compounds by radical cyclization: Use of glyoxylic acid hydrazone derivatives

Glyoxylic acid diphenylhydrazone (2a) and the corresponding O-benzyloxime (2b) are easily esterified in high yield by β-bromo alcohols. The resulting esters undergo radical cyclization to α-(2,2-diphenylhydrazino)- or α-[(phenylmethoxy)amino]lactones on treatment with tributyltin hydride. Esters for radical cyclization were also made using a β-(phenylseleno) alcohol and an enol ether. Several derivatives of glyoxylic acid were evaluated, but none was as effective as 2a or 2b. The imine 28 was prepared by an indirect route; it undergoes radical cyclization with displacement of the nitrogen substituent (28 → 30) so that an α-amino lactone can be generated by acid hydrolysis of the cyclization product.