Econazole

Econazole Basic information
Product Name:Econazole
Synonyms:1-(2-((4-chlorophenyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazol;1-(2,4-dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)-imidazol;1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole;ECONAZOLE;ECONAZOLUM;1-[2,4-Dichloro-β-[(p-chlorobenzyl)oxy]phenethyl]imidazole;1H-Imidazole, 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-;Imidazole, 1-[2,4-dichloro-β-[(p-chlorobenzyl)oxy]phenethyl]- (8CI)
CAS:27220-47-9
MF:C18H15Cl3N2O
MW:381.68
EINECS:248-341-6
Product Categories:FARESTON
Mol File:27220-47-9.mol
Econazole Structure
Econazole Chemical Properties
Melting point 86.8°C
Boiling point 533.8±50.0 °C(Predicted)
density 1.33±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Practically insoluble in water, very soluble in ethanol (96 per cent) and in methylene chloride.
pka6.68±0.12(Predicted)
form neat
Water Solubility 0.37g/L(ambient temperature)
CAS DataBase Reference27220-47-9(CAS DataBase Reference)
EPA Substance Registry SystemEconazole (27220-47-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36/37/39
MSDS Information
Econazole Usage And Synthesis
Chemical PropertiesWhite or almost white powder
OriginatorPevaryl,Cilag Chemie,France,1976
UsesEconazole (cas# 27220-47-9) is a compound useful in organic synthesis.
Usesantineoplastic, 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.
DefinitionChEBI: 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group. It is an ether, a member of imidazoles, a dichlorobenzene and a member of monochlorobenzenes.
IndicationsEconazole (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.
Manufacturing ProcessA suspension of 10.3 parts of α-(2,4-dichlorophenyl)-imidazole-1-ethanol and 2.1 parts of sodium hydride in 50 parts of dry tetrahydrofuran is stirred andrefluxed for 2 hours. After this reaction-time, the evolution of hydrogen is ceased. Then there are added successively 60 parts dimethylformamide and 8 parts of p-chlorobenzylchloride and stirring and refluxing is continued for another two hours. The tetrahydrofuran is removed at atmospheric pressure. The dimethylformamide solution is poured onto water. The product, 1-[2,4- dichloro-β-(p-chlorobenzyloxy)phenethyl]imidazole, is extracted with benzene. The extract is washed with water, dried, filtered and evaporated in vacuo. From the residual oily free base, the nitrate salt is prepared in the usual manner in 2-propanol by treatment with concentrated nitric acid, yielding, after recrystallization of the crude solid salt from a mixture of 2-propanol, methanol and diisopropylether, 1-[2,4-dichloro-β-(pchlorobenzyloxy)phenethyl]imidazole nitrate; MP 162°C.
Brand nameSpectazole (Johnson & Johnson).
Therapeutic FunctionAntifungal
SynthesisEconazole, 1-[2,4-dichloro-β-[(4-chlorobenzyl)oxy]phenethyl]-imidazole (35.2.8), is an analog of myconazole. It differs in the presence of a single chlorine atom in the benzyl part of the molecule, and it is synthesized in the same manner, except that it uses 4-chlorobenzylchloride in the last stage instead of 2,4-dichlorobenzylbromide.
Econazole Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->Acetone-->Sodium hydride-->Acetophenone-->Imidazole-->Aluminum-->4-Chlorobenzyl chloride-->2-Chlorobenzyl chloride-->Econazole nitrate-->Nitric acid
Preparation ProductsSULCONAZOLE
Econazole sulfosalicylate Econazole nitrate USP Ph.Eur (S)-Econazole MICONAZOLE NITRATE IMP. B (EP) AS NITRATE: ECONAZOLE NITRATE MM(CRM STANDARD) ECONAZOLE REFERENCE SPECTRUM EPY(CRM STANDARD) Methoxy ECONAZOLE NITRATE EPE(CRM STANDARD) (R)-Econazole 4,4'-Bis(chloromethyl)-1,1'-biphenyl ECONAZOLE NITRATE BP STANDARD(CRM STANDARD) ECONAZOLE NITRATE ASSAY STANDARD BP(CRM STANDARD) ECONAZOLE FOR SYSTEM SUITABILITY ECONAZOLE NITRATE REFERENCE SPECTRUM EPY(CRM STANDARD) Econazole Nitrate USP ECONAZOLE NITRATE--N/H MICONAZOLE NITRATE ECONAZOLE BASE ECONAZOLE NITRATE IMP. B (EP) AS NITRATE: (2RS)-2-[(4-CHLOROBENZYL)OXY]-2-(2,4-DICHLOROPHENYL)ETHANAMINE NITRATE MM(CRM STANDARD)

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