General Description
Colorless crystals.
Reactivity Profile
The triazoles, of which GUANAZOLE(1455-77-2) 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, GUANAZOLE(1455-77-2), 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. GUANAZOLE(1455-77-2) forms salts readily with acids.
Air & Water Reactions
This compound is sensitive to air. Dust can be explosive when suspended in air at specific concentrations. Water soluble.
Health Hazard
SYMPTOMS: This chemical is stable under normal laboratory conditions.
Fire Hazard
Flash point data for this chemical are not available. GUANAZOLE is probably combustible.
Chemical Properties
colourless crystals or faintly yellow powder
Uses
Inhibitor of DNA synthesis.
Definition
ChEBI: An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups.
Synthesis
1. 500 mL of water was added to a 2000 mL three-necked flask and 200.0 g of dicyandiamide was added with vigorous stirring for 20 minutes to form a turbid liquid.
2. 155 g of hydrazine sulfate was added to the cloudy liquid and the mixture was heated to 50°C. 3. 72 mL of 80% water was added slowly.
3. 72 mL of 80% hydrazine hydrate was added slowly, followed by warming the reaction system to 120°C to 125°C, during which all solids gradually dissolved.
4. the reaction mixture was stirred continuously at 120°C to 125°C for 16 hours, during which time a small amount of solids precipitated out of solution.
5. Upon completion of the reaction, the heating was stopped and the reaction mixture was cooled to room temperature.
6. The pH of the reaction mixture was adjusted to 9 by adding 100 mL of 10% sodium carbonate solution.
7. The reaction mixture was transferred to a 2 L dispensing funnel and the organic phase was extracted with 500 mL of dichloromethane.
8. The organic phase was washed with water and dried with anhydrous sodium sulfate.
9. Dichloromethane was removed by evaporation to give a white solid product.
10. The white solid was dried in a hot air oven to give a final product of 169 g of 3,5-diamino-1,2,4-triazole in 72% yield based on dicyandiamide.
Purification Methods
The triazole crystallises from water or EtOH. [Beilstein 26 III/IV 1161.]
References
[1] Patent: CN105968058, 2016, A. Location in patent: Paragraph 0073; 0074; 0075
[2] Chemische Berichte, 1912, vol. 45, p. 2733
[3] Journal fuer Praktische Chemie (Leipzig), 1913, vol. <2>88, p. 312
[4] Gazzetta Chimica Italiana, 1894, vol. 24, p. I 491
[5] Chemistry - A European Journal, 2010, vol. 16, # 5, p. 1572 - 1584
