119006-77-8

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes:

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Acute Tox. 4 (100%)
Skin Irrit. 2 (100%)
Eye Irrit. 2 (100%)
STOT SE 3 (100%)

Usage

Uses

Used in Antifungal Applications:
1-[(2-Fluorophenyl)-(4-fluorophenyl)phenylmethyl]-1H-imidazole is used as an antifungal agent for the treatment of mycosis of the skin. It exhibits excellent local and systemic tolerance in patients and is effective against both saprophytic and pathogenic fungi that affect animals and humans. The compound works by inhibiting fungal lanosterol 14α-demethylase, which is a crucial enzyme in the fungal cell membrane synthesis.
Used in Pharmaceutical Industry:
1-[(2-Fluorophenyl)-(4-fluorophenyl)phenylmethyl]-1H-imidazole is used as an active pharmaceutical ingredient in the development of antifungal medications. Its potent broad-spectrum activity and good tolerance make it a valuable compound for creating effective treatments for various fungal infections.
Used in Research and Development:
In the field of pharmaceutical research and development, 1-[(2-Fluorophenyl)-(4-fluorophenyl)phenylmethyl]-1H-imidazole serves as a key compound for studying the structure-activity relationship of imidazole antifungal agents. This knowledge can be applied to design and synthesize new, more effective antifungal drugs with improved properties.
Brand Name:
The brand name for 1-[(2-Fluorophenyl)-(4-fluorophenyl)phenylmethyl]-1H-imidazole is Micetal, which is a topical antifungal agent used for the treatment of skin mycoses.

Originator

Uriach (Spain)

InChI:InChI=1/C22H16F2N2/c23-19-12-10-18(11-13-19)22(26-15-14-25-16-26,17-6-2-1-3-7-17)20-8-4-5-9-21(20)24/h1-16H

Synthetic route

1H-imidazole (288-32-4) + (2-Fluorophenyl)(4-fluorophenyll)phenylchloromethane (128092-75-1) → flutrimazole (119006-77-8)

Conditions	Yield
With triethylamine In acetonitrile for 3h; Heating; Yield given;

o-fluorobenzophenone (342-24-5) → flutrimazole (119006-77-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) magnesium / 1.) terbutyl methyl ether, THF, iodine, dichloroethane, reflux, 30 min, 2.) reflux, 2.5 h 2: thionyl chloride / 4 h / Heating 3: triethylamine / acetonitrile / 3 h / Heating View Scheme

(2-fluorophenyl)-(4-fluorophenyl)phenylmethanol (128092-72-8) → flutrimazole (119006-77-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Heating 2: triethylamine / acetonitrile / 3 h / Heating View Scheme

1-Bromo-4-fluorobenzene (460-00-4) → flutrimazole (119006-77-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) magnesium / 1.) terbutyl methyl ether, THF, iodine, dichloroethane, reflux, 30 min, 2.) reflux, 2.5 h 2: thionyl chloride / 4 h / Heating 3: triethylamine / acetonitrile / 3 h / Heating View Scheme

Upstream product

• 288-32-4 1H-imidazole 
• 128092-75-1 (2-fluorophenyl)-(4-fluorophenyl)phenylchloromethane 
• 342-24-5 o-fluorobenzophenone 
• 128092-72-8 (2-fluorophenyl)-(4-fluorophenyl)phenylmethanol 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant academic research and scientific papers

Synthesis and antifungal activity of a series of difluorotritylimidazoles

1-[(2-Fluorophenyl)(4-fluorophenyl)phenylmethyl]-1H-imidazole (flutrimazole, UR-4056, CAS 119006-77-8) (15) was selected among a series of mono-, di- and trifluorotrityl-imidazole antifungal agents as the most potent fluorine containing analogue of clotrimazole.

1-((2-fluorophenyl)(4-fluorophenyl)phenylmethyl)-1H-imidazole useful as antifungal agent

The invention relates to 1-[(2-Fluorophenyl)(4-fluorophenyl)phenylmethyl]-1H-imidazole, useful as antifungal agent.