1H-1,2,4- triazole

Product Description

1H124Triazole is a heterocyclic compound containing a fivemembered ring made up of three nitrogen atoms and two carbon atoms with a hydrogen atom attached to one of the nitrogen atoms in the ring It is one of the most common triazole derivatives and has significant importance in chemistry and various fields such as pharmaceuticals and material science

 Chemical Details

 IUPAC Name 1H124Triazole  

 Molecular Formula C3H3N3  

 Molecular Weight 6907 gmol  

 Structure  

   A triazole ring with nitrogen atoms at positions 1 2 and 4 The H in 1H refers to the hydrogen atom at the 1position

 Physical Properties

 Appearance Colorless to pale yellow crystalline solid  

 Melting Point  7072C  

 Boiling Point  175C  

 Solubility Soluble in water and polar organic solvents like ethanol and acetone  

 Density 125 gcm

 Applications

1 Pharmaceuticals

    Antifungal Activity 1H124triazole derivatives are widely used as antifungal agents For example fluconazole itraconazole and voriconazole are derived from the triazole ring structure and are used to treat various fungal infections by inhibiting ergosterol biosynthesis

    Anticancer Potential Triazole derivatives are also explored for their anticancer properties particularly in inhibiting enzymes involved in DNA synthesis and repair

    Antiinflammatory and Antibacterial Activity Some derivatives show promise in antiinflammatory and antibacterial applications

2 Agriculture

    Fungicides Triazole compounds are used as fungicides in agriculture due to their ability to inhibit the biosynthesis of ergosterol which is crucial for fungal cell membranes

    Herbicides and Growth Regulators Some triazole derivatives are used to modify plant growth or as plant growth regulators in crops

3 Materials Science

    Coordination Chemistry The nitrogen atoms in the triazole ring can coordinate with metal centers making 1H124triazole useful in the synthesis of metalorganic frameworks MOFs or other coordination compounds

    Polymer Chemistry Triazole derivatives are used in the synthesis of specialized polymers often to impart unique properties like resistance to oxidation or enhanced mechanical strength

4 Chemical Synthesis

    Ligands in Organic Synthesis The triazole ring acts as a bidentate ligand for metals widely used in catalysis

    Reagents in Organic Synthesis 1H124Triazole is used as a building block in the synthesis of other functionalized heterocycles or complex organic molecules

 Chemical Reactivity

1 Nucleophilic Substitution

    The nitrogen atoms in the 124triazole ring can act as nucleophiles enabling substitution reactions in organic synthesis

2 Electrophilic Aromatic Substitution

    The triazole ring is activated at the positions 3 and 5 relative to the nitrogen atoms making it reactive in electrophilic substitution reactions

3 Coordination Chemistry

    The nitrogen atoms in the triazole ring can coordinate with metal centers forming stable chelates useful in catalytic processes or material science

 Synthesis of 1H124Triazole

1 From Hydrazine Derivatives

    One common synthetic route involves the reaction of hydrazine with an unsaturated ketone or other appropriate reagents to form the triazole ring

2 Via Cyclization of Azides

    Triazoles can be synthesized by cyclization of azides with alkynes or other electrophilic reagents providing a straightforward method for constructing the ring

3 From Amidrazones or Hydrazones

    Cyclization of amidrazones or hydrazones with appropriate electrophiles or acid catalysts leads to 1H124triazole

 Safety and Handling

 Toxicity  

    1H124Triazole and its derivatives should be handled with care as they may be harmful if ingested inhaled or absorbed through the skin

    It may cause irritation to the skin eyes and respiratory system

 Precautions  

    Use gloves protective eyewear and work in a wellventilated fume hood Always follow safety guidelines for handling chemicals

 Storage  

    Store in a cool dry place away from heat moisture and strong oxidizers Ensure containers are tightly sealed

Would you like additional information on specific derivatives of 1H124triazole its role in drug design or its use in coordination chemistry