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MICONAZOLE
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Name

MICONAZOLE

 EINECS 245-324-5
CAS No. 22916-47-8 Density 1.4 g/cm3
PSA 27.05000 LogP 6.45480
Solubility Freely soluble in alcohols or acetone. Also soluble in DMF or chloroform. Insoluble in water Melting Point 159-163 °C
Formula C18H14Cl4N2O Boiling Point 555.1 °C at 760 mmHg
Molecular Weight 416.134 Flash Point 289.5 °C
Transport Information N/A Appearance White powder.
Safety 22-36 Risk Codes 22
Molecular Structure Molecular Structure of 22916-47-8 (Miconazole) Hazard Symbols HarmfulXn
Synonyms

Imidazole,1-[2,4-dichloro-b-[(2,4-dichlorobenzyl)oxy]phenethyl]-(8CI);Daktanol;DaktarinIV;Florid-F;Lauriad;MJR 1762;Miconazole;Monistat IV;NSC 170986;R 18134;Zimybase;

Article Data 6

MICONAZOLE Synthetic route

94-99-5

2,4-Dichlorobenzyl chloride

24155-42-8

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

22916-47-8

miconazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Substitution;
Stage #2: 2,4-Dichlorobenzyl chloride In tetrahydrofuran at 45℃; for 16h; Substitution;		73%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;
Stage #2: 2,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 20℃;
874-42-0

2,4-dichlorobenzaldeyhde

22916-47-8

miconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 82 percent / aq. KOH / acetonitrile / 3 h / 60 °C
2.1: 63 percent / pyridine / ethanol / 12 h / Heating
3.1: NaH; HMPA / tetrahydrofuran / 0.5 h / 20 °C
3.2: 73 percent / tetrahydrofuran / 16 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium hydroxide / acetonitrile / 60 - 65 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere
3.2: 20 °C
View Scheme
13692-15-4

2-(2,4-dichlorophenyl)oxirane

22916-47-8

miconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 63 percent / pyridine / ethanol / 12 h / Heating
2.1: NaH; HMPA / tetrahydrofuran / 0.5 h / 20 °C
2.2: 73 percent / tetrahydrofuran / 16 h / 45 °C
View Scheme

2,4-dichlorobenzyl methanesulfonate

24155-42-8

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

22916-47-8

miconazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #2: 2,4-dichlorobenzyl methanesulfonate In N,N-dimethyl-formamide at 20℃; for 12h;		118 mg
1777-82-8

(2,4-dichlorophenyl)methanol

22916-47-8

miconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 2 h / 0 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C
2.2: 12 h / 20 °C
View Scheme
4252-78-2

2,2',4'-trichloroacetophenone

22916-47-8

miconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 12 h / 0 - 20 °C
2.1: sodium tetrahydroborate; methanol / dichloromethane / 2 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C
3.2: 12 h / 20 °C
View Scheme
46503-52-0

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

22916-47-8

miconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate; methanol / dichloromethane / 2 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C
2.2: 12 h / 20 °C
View Scheme
150994-84-6

4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobutanoic acid

22916-47-8

miconazole

4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobutanoate 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazol-1-ium

Conditions
ConditionsYield
In acetonitrile at 50℃; for 6h;100%
112-82-3

hexadecanyl bromide

22916-47-8

miconazole

1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-hexadecyl-1H-imidazol-3-ium bromide

Conditions
ConditionsYield
In acetonitrile at 70℃; for 12h;95%
111-83-1

1-bromo-octane

22916-47-8

miconazole

57264-59-2

1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-octyl-1H-imidazol-3-ium bromide

Conditions
ConditionsYield
In acetonitrile at 70℃; for 12h;93%
In acetonitrile for 2h; Reflux;93%

MICONAZOLE Chemical Properties

MF: C18H14Cl4N2O
MW: 416.13
EINECS: 245-324-5 
Mol File: 22916-47-8.mol
mp：  159-163°C
Synonyms:1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-imidazol;1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-imidazol;1-[2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-;Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-;micronazol;Minostate;mjr1762
The structure of Miconazole(22916-47-8) is:

            

MICONAZOLE Uses

1、Miconazole(22916-47-8) is an imidazole antifungal agent, developed by Janssen Pharmaceutica, and commonly applied topically or mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa.
2、Miconazole(22916-47-8) is also used in Ektachrome film developing (along with surfactants such as Photo-Flo) in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde.

MICONAZOLE Toxicity Data With Reference

1.   

sln-asn 410 µg/L

   MUREAV    Mutation Research. 79 (1980),169.
2.   

ivn-inf TDLo:104 mg/kg/4D-I

   MJAUAJ    Medical Journal of Australia. 146 (1987),57.
3.   

ipr-rat LD50:349 mg/kg

   ARZNAD    Arzneimittel-Forschung. Drug Research. 31 (1981),2145.
4.   

orl-mus LD50:872 mg/kg

   ARZNAD    Arzneimittel-Forschung. Drug Research. 31 (1981),2145.
5.   

ipr-mus LD50:451 mg/kg

   ARZNAD    Arzneimittel-Forschung. Drug Research. 31 (1981),2145.
6.   

ivn-dog LD50:60 mg/kg

   DRUGAY    Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. 19 (1980),7.
7.   

ivn-mam LD50:100 mg/kg

   DRUGAY    Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. 19 (1980),7.

MICONAZOLE Safety Profile

Hazard Codes：  Xn
Risk Statements：  Harmful if swallowed
Safety Statements：  Wear suitable protective clothing
RIDADR：  3249
HazardClass：  6.1(b)
PackingGroup：  III
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl− and NOx.

MICONAZOLE Specification

1、Handling and Storage 
Storage：Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling：Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
2、Fire Fighting
Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing media: Use agent most appropriate to extinguish fire. In case of fire use water spray, dry chemical, carbon dioxide, or appropriate foam.
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