Econazole

Base Information

• Chemical Name: Econazole
• CAS No.: 27220-47-9
• Deprecated CAS: 68797-30-8
• Molecular Formula: C₁₈H₁₅Cl₃N₂O
• Molecular Weight: 381.689
• European Community (EC) Number: 248-341-6
• NSC Number: 187789
• UNII: 6Z1Y2V4A7M
• DSSTox Substance ID: DTXSID2029872
• Nikkaji Number: J10.724G,J304.909D,J306.630D
• Wikipedia: Econazole
• Wikidata: Q417141
• NCI Thesaurus Code: C61740
• RXCUI: 3743
• Pharos Ligand ID: PCDF78AF18JM
• Metabolomics Workbench ID: 43352
• ChEMBL ID: CHEMBL808
• Mol file: 27220-47-9.mol

Synonyms:Econazole;Econazole Nitrate;Ekonazole;Gyno Pervaryl 150;Gyno Pevaril;Gyno Pevaryl;Gyno-Pervaryl 150;Gyno-Pevaril;Gyno-Pevaryl;GynoPevaril;Nitrate, Econazole;Pevaryl

Chemical Property of Econazole

Chemical Property:

• Melting Point: 86.8 °C
• Boiling Point: 533.8 °C at 760 mmHg
• PKA: 6.68±0.12(Predicted)
• Flash Point: 276.6 °C
• PSA: 27.05000
• Density: 1.33 g/cm³
• LogP: 5.80140
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Practically insoluble in water, very soluble in ethanol (96 per cent) and in methylene chloride.
• Water Solubility.: 0.37g/L(ambient temperature)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 380.024996
• Heavy Atom Count: 24
• Complexity: 379

Purity/Quality:

99%, ^*data from raw suppliers

Econazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl
• Uses: antineoplastic, anti-estrogen. Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14 demethylation of sterols, interfering with the biosynthesis of ergosterol, which results in disorganization of the fungal plasma cell membrane and increased permeability. It is active against dermatophytes, yeast, P. orbiculare, Aspergillus, Cladosporium, and Sporothrix. Econazole (cas# 27220-47-9) is a compound useful in organic synthesis.
• Indications: Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14 demethylation of sterols, interfering with the biosynthesis of ergosterol, which results in disorganization of the fungal plasma cell membrane and increased permeability. It is active against dermatophytes, yeast, P. orbiculare, Aspergillus, Cladosporium, and Sporothrix.
• Therapeutic Function: Antifungal

Technology Process of Econazole

There total 7 articles about Econazole 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: 62.4%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → econazole (27220-47-9,68797-30-8,73094-37-8,73094-39-0)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at -5 - 20 ℃; for 1.5h; Inert atmosphere;

4-chlorobenzyl halide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2018.02.014

Reference yield:

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone (46503-52-0) → econazole (27220-47-9,68797-30-8,73094-37-8,73094-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 20 °C

2: potassium iodide / acetonitrile / Reflux

With sodium tetrahydroborate; potassium iodide; In methanol; acetonitrile;

DOI:10.1039/C6SC05368H

Reference yield:

2,2',4'-trichloroacetophenone (4252-78-2) → econazole (27220-47-9,68797-30-8,73094-37-8,73094-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetonitrile

2: sodium tetrahydroborate / methanol / 20 °C

3: potassium iodide / acetonitrile / Reflux

With sodium tetrahydroborate; potassium carbonate; potassium iodide; In methanol; acetonitrile;

DOI:10.1039/C6SC05368H

upstream raw materials:

2,2',4'-trichloroacetophenone

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone

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

2,4-dichlorophenacyl bromide

Downstream raw materials:

(S)-1-(2-((4-chlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

(R)-1-[2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

1-[2,4-Dichloro-β-(p-chlorobenzyloxy)phenethyl]-3-(p-fluorophenacyl)imidazolium chloride

Refernces

• 1、 Zhang, Lan,Fu, Leilei,Zhang, Shouyue,Zhang, Jin,Zhao, Yuqian,Zheng, Yaxin,He, Gu,Yang, Shengyong,Ouyang, Liang,Liu, Bo. "Discovery of a small molecule targeting ULK1-modulated cell death of triple negative breast cancer in vitro and in vivo". . p. 2687 - 2701. Retrieved 2017/04/06.