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Home > Encyclopedia > 3,5-Diamino-1,2,4-triazole

3,5-Diamino-1,2,4-triazole

3,5-Diamino-1,2,4-triazole structure

3,5-Diamino-1,2,4-triazole 

structure
  • CAS No:

    1455-77-2

  • Formula:

    C2H5N5

  • Chemical Name:

    3,5-Diamino-1,2,4-triazole

  • Synonyms:

    1H-1,2,4-Triazole-3,5-diamine;Guanazole;3,5-Diamino-1,2,4-triazole;3,5-Diamino-s-triazole;NSC 1895;3,5-Diamino-1H-1,2,4-triazole;NSC 166592;NSC 167391;NSC 167392;503-88-8

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

colourless crystals or faintly yellow powderChEBI: An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups.Colorless crystals.


Guanazole appears as colorless crystals. (NTP, 1992)


Guanazole appears as colorless crystals. (NTP, 1992)|Guanazole is an aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups. It has a role as an antineoplastic agent, an EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor and a DNA synthesis inhibitor. It is a member of triazoles and an aromatic amine.|Guanazole is a cytostatic triazole derivative antimetabolite. Guanazole scavenges tyrosine free radicals, thereby inhibiting mammalian ribonucleotide reductase activity and DNA synthesis. (NCI04)

3,5-Diamino-1,2,4-triazole Basic Attributes

99.09

99.09

215-937-2

I01TWM5267

1895

DTXSID0025367

C531

29339990

Characteristics

93.6

-0.7

Guanazole appears as colorless crystals. (NTP, 1992)

1.686±0.06 g/cm3(Predicted)

205 °C (decomp)

473.7±28.0 °C(Predicted)

271.6±11.2 °C

1.7330 (estimate)

H2O: clear to hazy ;soluble in water.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 .

Store in a cool, dry place. Keep container closed when not in use.

3.85E-09mmHg at 25°C

This compound is sensitive to air. Dust can be explosive when suspended in air at specific concentrations. Water soluble.

Amines, Phosphines, and Pyridines

Explosive

The triazoles, of which GUANAZOLE 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, 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 forms salts readily with acids. (NTP, 1992)

Safety Information

3

R22

36/37-45-36/37/39-27-26

XZ4535000

Xn,Xi,C

Stability Air sensitive. Reacts with acids and oxidizing agents.

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P501

H302

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Warning|H302 (99.55%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 273 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to air, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Drug Information

SYMPTOMS: This chemical is stable under normal laboratory conditions. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

3,5-diamino-1,2,4-triazole

3,5-Diamino-1,2,4-triazole Use and Manufacturing

Methods of Manufacturing

500mL water was added into a 2000ml three-necked flask, Then 200.0 g of dicyandiamide was stirred vigorously for 20 minutes to form a cloudy liquid, Then 155g hydrazine sulfate added, And the mixture was heated to 50 °C. 80percentconcentrationof hydrazine hydrate 72 ml are added and the reaction heated to 120 °C to 125 °C during which time all the solids slowly dissolve. The reaction was stirred at this temperature for 16 hours. After this time, a small amount of solids precipitated from the solution. After the reaction was completed, heating was stopped and the reaction mixture was cooled to room temperature. Add 100 mL of 10percent strength sodium carbonate solution to adjust pH to 9 .The reaction was transferred to a 2 L separatory funnel, the organic phase was extracted with 500 mL of dichloromethane, the organic phase was washed with water and dried over anhydrous sodium sulfate, evaporation of methylene chloride gave a white solid, After drying in a hot air oven, 169 g of white 3, 5-diamino 1, 2, 4-triazole (yield based on dicyandiamide: 72percent) was obtained. .A 10 L autoclave was charged with 2.5 Kg of copper hydroxide (98percent), 3.0 Kg of ammonium chloride (99percent) and cyanamine (50percent) 4.2 Kg. The amount of material to be cast is only 1: 2.2: 2, In sealed and stirred state, The autoclave was pressurized and slowly warmed to 110 degrees Celsius. After 3 hours of reaction, the reaction temperature was slowly lowered to room temperature and a dark red solid was obtained after filtration. transfer the red solid to a 50L glass reaction kettle, 25 L of 1.4 kg sodium sulfide in water was added.Heated to reflux for 30 minutes to produce a red precipitate, the mixture was filtered through a filter cartridge to the extraction kettle, In the extraction vessel was added 15L dichloromethane, the organic phase was extracted, evaporated to dryness dichloromethane to give a white solid, After drying in a hot air oven, 2.2 kg of white 3, 5-diamino 1, 2, 4-triazole(yield: 88percent in terms of cyanamide) was obtained.

Uses

Inhibitor of DNA synthesis.

1H-1,2,4-Triazole-3,5-diamine: ACTIVE

Computed Properties

Molecular Weight:99.10
XLogP3:-0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Exact Mass:99.05449518
Monoisotopic Mass:99.05449518
Topological Polar Surface Area:93.6
Heavy Atom Count:7
Complexity:63.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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