537-17-7

Basic information

• Product Name: Amanozine
• Synonyms: Amanozine;2-Amino-4-anilino-s-triazine;N-Phenyl-1,3,5-triazine-2,4-diamine;(4-amino-s-triazin-2-yl)-phenyl-amine;2-N-phenyl-1,3,5-triazine-2,4-diamine;2-Amino-4-anilino-1,3,5-triazin;Amanozina;Amanozinum
• CAS NO: 537-17-7
• Molecular Formula: C₉H₉N₅
• Molecular Weight: 187.21
• Mol File: 537-17-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 235-236°
• Boiling Point: 311.95°C (rough estimate)
• Flash Point: 215.5 °C
• Appearance: /
• Density: 1.2986 (rough estimate)
• Refractive Index: 1.6900 (estimate)
• PKA: 3.79±0.10(Predicted)
• CAS DataBase Reference: Amanozine(CAS DataBase Reference)
• NIST Chemistry Reference: Amanozine(537-17-7)
• EPA Substance Registry System: Amanozine(537-17-7)

Safety Data

• Hazardous Substances Data: 537-17-7(Hazardous Substances Data)

Usage

Originator

Amanozine,Onbio Inc.

Manufacturing Process

21.3 g (0.1 mole) of 1-phenylbiguanide hydrochloride were dissolved in hot water and the solution was added to 5.3 g (0.05 mole) sodium carbonate by stirring. On cooling 15 g of the needle crystals have fallen. They were heated to reflux with 80 ml of dry formic acid. Then 40-50 ml formic acid was distilled off. The residue was with water diluted, cooled with ice and the conc. alkali was added. The precipitate fallen. It was filtered off and recrystallized from 40-50% ethanol. The pure product 4-amino-2-anilino-1,3,5-triazine had MP: 232°-233°C. Monochlorohydrate of it crystallized as long colorless needles melted at 258°- 260°C.

Therapeutic Function

Diuretic

Purification Methods

It crystallises from dioxane or 50% aqueous EtOH. [Beilstein 26 III/IV 1195.]

InChI:InChI=1/C9H9N5/c10-8-11-6-12-9(14-8)13-7-4-2-1-3-5-7/h1-6H,(H3,10,11,12,13,14)

Upstream product

• 64-18-6 formic acid 
• 102-02-3 1-phenylbiguanide 
• 109-94-4 formic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 106-47-8 4-chloro-aniline 
• 99056-81-2 {4-amino-6-(phenylamino)-[1,3,5]triazin-2-yl}methanol 
• 18655-47-5 triformylmethane 
• 55-57-2 1-phenylbiguanide monohydrochloride 
• 62-53-3 aniline 
• 127099-85-8 N-Cyanoguanidine 
• 122-51-0 orthoformic acid triethyl ester 
• 77287-34-4 formamide 
• 41410-39-3 1-phenyl-3-cyanoguanidine 
• 101080-83-5 4-amino-6-(phenylamino)-1,3,5-triazine-2-carboxylic acid 

Downstream Products

• 90484-63-2 N²-(2,4-dibromo-phenyl)-[1,3,5]triazine-2,4-diyldiamine 
• 72274-25-0 N-(4-bromo-phenyl)-[1,3,5]triazine-2,4-diamine 

Relevant articles and documents

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source

1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.

Diuretics on the basis of N substituted 2,4 diamino s triazines by cyclisation of biguanides

The structural class of 2,4 diamino s triazines (5) functioning as diuretics has become accessible by a novel preparatory procedure. The new synthesis is based on the aminomethinylating principle of s triazine (1), under the action of which biguanides (2) are cyclized to 5 passing through the intermediary states 3 and 4.