1455-77-2

Basic information

• Product Name: 1H-1,2,4-Triazole-3,5-diamine
• Synonyms: 4H-1,2,4-TRIAZOLE-3,5-DIAMINE;3-AMINO-1H-1,2,4-TRIAZOL-5-YLAMINE;3,5-DIAMINO-1,2,4-TRIAZOLE;3,5-DIAMINO-1H-1,2,4-TRIAZOLE;1H-1,2,4-TRIAZOLE-3,5-DIAMINE;GUANAZOLE;TIMTEC-BB SBB004371;1,2,4-Triazolidine, 3,5-diimino-
• CAS NO: 1455-77-2
• Molecular Formula: C₂H₅N₅
• Molecular Weight: 99.09
• EINECS: 215-937-2
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Triazoles
• Mol File: 1455-77-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 202-205 °C(lit.)
• Boiling Point: 473.7 °C at 760 mmHg
• Flash Point: 271.6 °C
• Appearance: white/powder
• Density: 1.686 g/cm³
• Vapor Pressure: 3.85E-09mmHg at 25°C
• Refractive Index: 1.7330 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: clear to hazy
• PKA: 12.10±0.40(Predicted)
• Water Solubility: Soluble in water.
• Stability: Stability Air sensitive. Reacts with acids and oxidizing agents.
• BRN: 112467
• CAS DataBase Reference: 1H-1,2,4-Triazole-3,5-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,4-Triazole-3,5-diamine(1455-77-2)
• EPA Substance Registry System: 1H-1,2,4-Triazole-3,5-diamine(1455-77-2)

Safety Data

• Hazard Codes: Xn,Xi,C
• Statements: 22-34
• Safety Statements: 36/37-45-36/37/39-27-26
• WGK Germany: 3
• RTECS: XZ4535000
• TSCA: Yes
• Hazardous Substances Data: 1455-77-2(Hazardous Substances Data)

Usage

Chemical Properties

colourless crystals or faintly yellow powder

Uses

Different sources of media describe the Uses of 1455-77-2 differently. You can refer to the following data:
1. Inhibitor of DNA synthesis.
2. 3,5-Diamino-1,2,4-triazole is used as an inhibitor of DNA synthesis. It also serves as an antitumor agents in the treatment of epigenetically-based diseases. It acts as a corrosion inhibitor for copper.

Definition

ChEBI: An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups.

General Description

Colorless crystals.

Air & Water Reactions

1H-1,2,4-Triazole-3,5-diamine is sensitive to air. Dust can be explosive when suspended in air at specific concentrations. Water soluble.

Reactivity Profile

The triazoles, of which 1H-1,2,4-Triazole-3,5-diamine is a member, are a group of highly explosive materials that are sensitive to heat, friction, and impact. Sensitivity varies with the type of substitution to the triazole ring. The amine substituted derivatives, 1H-1,2,4-Triazole-3,5-diamine, tend not to be explosion sensitive. Metal chelated and halogen substitution of the triazol ring make for a particularly heat sensitive material. Azido and nitro derivatives have been employed as high explosives. No matter the derivative these materials should be treated as explosives. 1H-1,2,4-Triazole-3,5-diamine forms salts readily with acids.

Health Hazard

SYMPTOMS: 1H-1,2,4-Triazole-3,5-diamine is stable under normal laboratory conditions.

Fire Hazard

Flash point data for 1H-1,2,4-Triazole-3,5-diamine are not available. 1H-1,2,4-Triazole-3,5-diamine is probably combustible.

Safety Profile

Human systemic effects by intravenous route: leukopenia (reduced white blood cell count) and thrombo cytopenia (reduced blood platelet count). Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

The triazole crystallises from water or EtOH. [Beilstein 26 III/IV 1161.]

InChI:InChI=1/C2H5N5/c3-1-5-2(4)7-6-1/h(H5,3,4,5,6,7)

Upstream product

• 127099-85-8 N-Cyanoguanidine 
• 420-04-2 CYANAMID 
• 77287-34-4 formamide 
• 7803-57-8 hydrazine hydrate 
• 86147-15-1 1-acetyl-3,5-diamino-1H-1,2,4-triazole 
• 64-17-5 ethanol 
• 131023-09-1 methyl (3,5-diamino-1,2,4-triazol-1-yl)dithiocarbonate 
• 60-34-4 methylhydrazine 

Downstream Products

• 85599-38-8 Acetic acid 3-(2-amino-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-propyl ester 
• 13223-53-5 2-Amino-s-triazolo<2,3-a>pyrimidin 
• 80616-61-1 3-amino-5-p-nitrobenzamido-1,2,4-triazole 
• 80616-62-2 3,5-bis-p-nitrobenzamido-1,2,4-triazole 
• 135370-69-3 5-(4-Dimethylamino-phenyl)-7-phenyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine 
• 109929-40-0 <3(5)-amino-1H-1,2,4-triazol-5(3)-yl>-2,4,6-triphenylpyridinium tetrafluoroborate 
• 80616-55-3 3-acetylamino-5-amino-1H-1,2,4-triazole 
• 124638-99-9 3,5-diamino-1-dodecyl-1,2,4-triazole 
• 76071-60-8 2-amino-5,7-diphenyl-1,2,4-triazolo<1,5-a>pyrimidine 
• 134834-75-6 2-amino-5,7-diphenyl-4,7-dihydro-1,2,4-triazolo<1,5-a>pyrimidine 
• 53246-51-8 3,5-diaminobenzoyl-1,2,4-triazole 
• 116986-36-8 3,5-diamino-1-methylcarbamoyl-1H-1,2,4-triazole 
• 103906-34-9 2-amino-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine 
• 134834-71-2 5-(4-Chloro-phenyl)-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine 

Relevant articles and documents

Efficient in situ synthesis of 3,5-disubstituted-1,2,4-triazoles under microwave-assisted conditions

Abstract Based on an efficient in situ metal/ligand reaction, a serial of 3,5-disubstituted-1, 2,4-triazoles were synthesized via cycloaddition of organonitriles and ammonia under microwave conditions. This synthetic protocol provides a concise and high-yield access to 3,5-disubstituted-1,2,4-triazoles in organic synthesis. Moreover, the tautomerism of the product was also investigated. Taylor & Francis Group, LLC.

Technology for three-innovation synthesis of 2-amino-5-methyl-4-oxo-3-n-propyltriazolopyrimidine

The invention discloses a technology for synthesizing 2-amino-5-methyl-4-oxo-3-n-propyl-6H-triazolo-[1,5-a]pyrimidine. Methyl methacrylate and bromine are firstly subjected to an addition reaction toprepare methyl 2,3-dibromo-2-methylpropanoate, and then the methyl 2,3-dibromo-2-methylpropanoate and sodium methylate are etherified in a new suitable solvent to prepare methyl 3,3-dimethoxy-2-methylpropionate etherate; the etherate and 3,5-diamino-1,2,4-triazole, prepared from hydrazine hydrate and dicyandiamide under the catalysis of an acid, are condensed at an intermediate temperature of about 115 DEG C under the catalysis of an organic base to obtain a pyrimidotriazole compound; and the pyrimidotriazole material liquid and 1-chloropropane undergo a direct alkylation reaction in an inorganic or organic bas and a new solvent to obtain the 2-amino-5-methyl-4-oxo-3-n-propyl-6H-triazolo-[1,5-a]pyrimidine. The technology is improved by the three major innovations of improving the catalyticsynthesis conditions of the condensation ring closure of the pyrimidotriazole, optimizing the alkylation substitution reaction and the process technology of the pyrimidinetriazole and innovating theraw material of an alkylation reagent, so the technology has the advantages of great improvement of the yield, simplicity in operation, mild reaction conditions, and safety to devices and human bodies, the total yield of methyl methacrylate can reach 46.5% or above, and the obtained product has a white color and a good crystalline state, and has a content of 99% or more.

Hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole

The invention provides a hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole. The method comprises the following steps: cyan substituted derivatives, ammonium salt, copper hydroxide and water are used as raw materials, hydrothermal synthesis is carried out in a condition with high pressure, and 3,5-diamino-1,2,4-triazole is obtained. Cyanamide, ammonium salt, and copper hydroxide are used as raw materials, a high pressure reaction apparatus is used, ammonia which is decomposed from the ammonium salt in the effects of copper hydroxide and two molecules of cyanamide are condensed, in order to generate a copper biguanide complex. Copper(I) sulfide is eliminated from the copper biguanide complex in a condition with existence of sulfide, and 3,5-diamino-triazole is obtained by a cyclocondensation reaction. A high pressure reaction vessel is used for increasing the concentration of ammonia in a water system, which is good for generation of the condensation reaction, and at the same time, time and temperature required for condensation of cyanamide are effectively reduced. Existence of excess ammonium salt is used, in order to stabilize the pH value of the whole reaction system, and generation of the side reaction of polymerization of cyanamide is avoided. The method has the advantages of simple process, low raw material cost, and high purity of the final product.