Fenticonazole

Base Information

• Chemical Name: Fenticonazole
• CAS No.: 72479-26-6
• Molecular Formula: C24H20Cl2N2OS
• Molecular Weight: 455.408
• UNII: QG05NRB077
• DSSTox Substance ID: DTXSID7057812
• Nikkaji Number: J11.264J
• Wikipedia: Fenticonazole
• Wikidata: Q3068413
• NCI Thesaurus Code: C72963
• Metabolomics Workbench ID: 154244
• ChEMBL ID: CHEMBL1651990
• Mol file: 72479-26-6.mol

Synonyms:1-(2,4-dichloro-beta-((p-(phenylthio)benzyl)oxy)phenethyl)imidazole;Fenizolan;fenticonazole;fenticonazole mononitate;Laurimic;Lomexin;Micofulvin;Rec 15-1476;Terlomexin

Chemical Property of Fenticonazole

Chemical Property:

• Boiling Point: 637.2 °C at 760 mmHg
• Flash Point: 339.2 °C
• PSA: 52.35000
• Density: 1.26 g/cm³
• LogP: 7.29920
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 454.0673398
• Heavy Atom Count: 30
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

FenticonazoleNitrate-d9 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SC2=CC=C(C=C2)COC(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl
• Uses: Antifungal. Isotope labelled Fenticonazole Nitrate broad spectrum antimycotic; also active as antibacterial. Antifungal (topical).
• Therapeutic Function: Antifungal

Technology Process of Fenticonazole

There total 5 articles about Fenticonazole 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-hydroxymethylphenyl phenyl sulfide (6317-56-2) → α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobenzyl ether (72479-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / aqueous HCl (d 1.18) / petroleum ether / 6 h / 20 - 25 °C

2: 1.) 50percent NaH / 1.) HMPA, 20 degC - 25 degC, 1 h; 50 degC - 60 degC, 2 h; 2.) 50 degC, 20 h

With hydrogenchloride; sodium hydride; In Petroleum ether;

Reference yield:

4-(phenylthio)benzoic acid (6310-24-3) → α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobenzyl ether (72479-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaBH₄/AlCl₃ / bis-(2-methoxy-ethyl) ether / 2 h / 25 °C

2: 93 percent / aqueous HCl (d 1.18) / petroleum ether / 6 h / 20 - 25 °C

3: 1.) 50percent NaH / 1.) HMPA, 20 degC - 25 degC, 1 h; 50 degC - 60 degC, 2 h; 2.) 50 degC, 20 h

With hydrogenchloride; sodium tetrahydroborate; aluminium trichloride; sodium hydride; In diethylene glycol dimethyl ether; Petroleum ether;

Reference yield:

1-phenylthio-4-chloromethyl-benzene (1208-87-3) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobenzyl ether (72479-26-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) HMPA, 20 degC - 25 degC, 1 h; 50 degC - 60 degC, 2 h; 2.) 50 degC, 20 h;

upstream raw materials:

1-phenylthio-4-chloromethyl-benzene

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

4-(phenylthio)benzoic acid

4-hydroxymethylphenyl phenyl sulfide

Refernces

• 1、 Tajana,Sibilia,Cappelletti,Cova,Nardi. "Physico-chemical, structural and analytical studies on fenticonazole, a new drug with antimycotic properties". . p. 2127 - 2133. Retrieved 2007/10/02.