4656-86-4

Basic information

• Product Name: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one
• Synonyms: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one;4,5-Dihydro-1H-imidazo[4,5-d]-1,2,3-triazin-4-one;7H-Imidazo[4,5-d]-1,2,3-triazine-4(3H)-one;3,7-Dihydro-4H-iMidazo[4,5-d]-1,2,3-triazin-4-one;3,7-Dihydro-4H-IMidazo[4,5-d]-v-triazin-4-one;NSC 22419;Dacarbazine IMpurity A (3,7-Dihidro-4H-IMidazo[4,5-d][1,2,3]triazin-4-One);Dacarbazine Related Compound B (50 mg) (2-azahypoxanthine monohydrate)
• CAS NO: 4656-86-4
• Molecular Formula: C₄H₃N₅O
• Molecular Weight: 137.09952
• EINECS: 225-096-3
• Mol File: 4656-86-4.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 512.9°C at 760 mmHg
• Flash Point: 264°C
• Appearance: /
• Density: 2.263g/cm³
• Vapor Pressure: 1.25E-10mmHg at 25°C
• Refractive Index: 2.088
• PKA: 8.66±0.20(Predicted)
• CAS DataBase Reference: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(4656-86-4)
• EPA Substance Registry System: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(4656-86-4)

Safety Data

• Hazardous Substances Data: 4656-86-4(Hazardous Substances Data)

Usage

Uses

2-Azahypoxanthine is a major degradation product of Dacarbazine (D101400). 2-Azahypoxanthine is possibly linked with some adverse effects of Dacarbazine (D1014000.

InChI:InChI=1/C4H3N5O/c10-4-2-3(6-1-5-2)7-9-8-4/h1H,(H2,5,6,7,8,10)

Upstream product

• 72-40-2 5-amino-1H-imidazole-4-carboxamide monohydrochloride 
• 188612-55-7 5-amino-N 1-ethyl-1H-imidazole-1,4-dicarboxamide 
• 7008-85-7 5-diazoimidazole-4-carboxamide 
• 360-97-4 5-Aminoimidazole-4-carboxamide 
• 97378-14-8 5-(2-hydroxy-naphthalen-1-ylazo)-1⁽³⁾H-imidazole-4-carboxylic acid amide 
• 308321-34-8 5-(2-hydroxy-5-methyl-phenylazo)-1H-imidazole-4-carboxylic acid amide 
• 91026-74-3 5-Acetamidoimidazole-4-carboxamide 
• 4342-03-4 5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide 
• 88795-61-3 4-ethoxyimidazo<4,5-d>-1,2,3-triazine 
• 88795-60-2 4-methoxyimidazo<4,5-d>-1,2,3-triazine 
• 64-17-5 ethanol 
• 49850-59-1 6-(Methylthio)-2-azapurine 
• 67-56-1 methanol 
• 188612-53-5 5-amino-N₁-methyl-1H-imidazole-1,4-dicarboxamide 

Downstream Products

• 82145-46-8 2-Aza-7-(2-benzoyloxyethoxymethyl)hypoxanthine 
• 82145-47-9 2-Aza-9-(2-benzoyloxyethoxymethyl)hypoxanthine 
• 113642-30-1 3-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propyl}-3,5-dihydro-imidazo[4,5-d][1,2,3]triazin-4-one 
• 56220-50-9 7-(2-Deoxy-β-D-erythro-pentafuranosyl)-7H-imidazo[4,5-d][1,2,3]triazin-4-one 

Relevant articles and documents

Validated spectral manipulations for determination of an anti-neoplastic drug and its related impurities including its hazardous degradation product

Innovative and specific double dual wavelength, dual ratio subtraction spectrophotometric methods were carried out along with a successive ratio subtraction spectrophotometric method for determination of dacarbazine and its related impurities including toxic and hazardous ones. For determination of dacarbazine by the double dual wavelength method, the absorbance differences between 323 and 350 nm of the zero order absorption spectra of dacarbazine were used. The values of absorbance difference between 267.2 and 286.2 nm of the zero order spectra of 5-amino-imidazole-4 carboxamide were used for its determination by the dual ratio subtraction method. The zero order absorption spectrum of 2-azahypoxanthine at 235 nm was used for its determination after applying the successive ratio subtraction method. ICH guidelines were followed for validation of the developed methods, where linear relationships were obtained in the range of 4-20, 1-16, and 2-20 μg mL?1for dacarbazine, 5-amino imidazole-4-carboxamide and 2-azahypoxanthine, respectively. Accurate, precise, and specific results were obtained upon applying the proposed methods according to ICH guidelines. Furthermore, the developed methods were successfully applied for determination of dacarbazine in its pharmaceutical formulation. Comparing the results of the developed methods with those of the official USP spectrophotometric method statistically showed no significant difference. The developed methods don't need any sophisticated techniques so they are considered cost effective methods. Moreover, the introduced methods have the advantages of being green where water was used as a solvent. The methods proved to be more economic, fast and simple than other reported HPLC methods.

PASE synthesis of 1-azolyl-1H-1,2,4-triazoles by the reaction of diazoazoles with ethyl isocyanoacetate

PASE (pot, atom and step economic) synthesis of 1-azolyl-1H-1,2,4-triazole derivatives in up to 91% yield has been accomplished by addition of 5-diazoazoles to ethyl isocyanoacetate.

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Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

We describe a practical, large-scale synthesis of the "fairy- ring" plant-growth regulator 2-azahypoxanthine (AHX), and its biologically active hydroxyl metabolite (AOH) and riboside derivative (AHXr). AHXr, a biosynthetic intermediate, was synthesized from inosine via a biomimetic route. Biotinylated derivatives of AHX and AHXr were also synthesized as probes for mechanistic studies. This journal is the Partner Organisations 2014.