Triaconazole

Base Information

• Chemical Name: Triaconazole
• CAS No.: 67915-31-5
• Molecular Formula: C26H31 Cl2 N5 O3
• Molecular Weight: 532.47
• Hs Code.: 2934990002
• NSC Number: 331942
• DSSTox Substance ID: DTXSID40860847
• Wikidata: Q27156516
• ChEMBL ID: CHEMBL1714574
• Mol file: 67915-31-5.mol

Synonyms:1-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine;Fungistat;Gyno-Terazol;R 42470;Terazol;terconazole

Chemical Property of Triaconazole

Chemical Property:

• Vapor Pressure: 1.91E-18mmHg at 25°C
• Melting Point: 126.3 ºC
• Boiling Point: 681.8°Cat760mmHg
• PKA: 8.33±0.10(Predicted)
• Flash Point: 366.2°C
• PSA: 64.88000
• Density: 1.35g/cm³
• LogP: 4.46560
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble1mg/mL
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 531.1803953
• Heavy Atom Count: 36
• Complexity: 693

Purity/Quality:

99%, ^*data from raw suppliers

Terconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-53
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl
• General Description: Terconazole is a triazole-based antifungal agent with demonstrated efficacy against vaginal candidosis and dermatophytosis in animal models. Its synthesis involves a multi-step process, including coupling reactions and saponification, leading to a compound with potent topical antifungal activity. This makes it a promising candidate for treating superficial fungal infections.

Technology Process of Triaconazole

There total 5 articles about Triaconazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(p-methoxyphenyl)piperazine dihydrochloride (38869-47-5,70849-64-8) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, NaOAc / 10percent Pd/C / methanol

2: 85 percent / 48percent HBr / Heating

3: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With hydrogen bromide; hydrogen; sodium acetate; sodium hydride; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00358a032

Reference yield:

(+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate (61397-56-6) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 3.) aq. NaOH

2: 87 percent / pyridine

3: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With pyridine; sodium hydroxide; sodium hydride;

DOI:10.1021/jm00358a032

Reference yield:

cis-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol (67914-85-6) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine

2: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With pyridine; sodium hydride;

DOI:10.1021/jm00358a032

upstream raw materials:

cis-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate

4-(4-hydroxyphenyl)-1-(1-methylethyl)piperazine

4-(p-methoxyphenyl)piperazine dihydrochloride

(+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate

Refernces

Antimycotic Azoles. 6. Synthesis and Antifungal Properties of Terconazole, a Novel Triazole Ketal

10.1021/jm00358a032

The research focuses on the synthesis and antifungal properties of terconazole, a novel triazole ketal. The synthesis process involves several key chemicals and steps. Starting from cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate (4), the sodium salt of triazole is coupled with the bromomethyl ketal in Me2SO at 130°C to produce a mixture of triazole derivatives. These derivatives are then saponified with NaOH in dioxane-water to yield alcohols 5 and 6. Alcohol 5 is converted to the corresponding methanesulfonate 7, which is coupled with the sodium salt of phenol 8 to give terconazole 3b. Phenol 8 is prepared from 1-(4-methoxyphenyl)piperazine (9) through reductive alkylation with acetone and demethylation with 48% HBr solution. The synthesized terconazole exhibits high topical in vivo activity against vaginal candidosis in rats and dermatophytosis in guinea pigs, showing potential as an effective treatment for superficial fungal infections.

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