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Basic Information
| CAS No.: | 22916-47-8 |
|---|---|
| Name: | Miconazole |
| Article Data: | 6 |
| Molecular Structure: | |
|
|
|
| Formula: | C18H14Cl4N2O |
| Molecular Weight: | 416.134 |
| 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; |
| EINECS: | 245-324-5 |
| Density: | 1.4 g/cm3 |
| Melting Point: | 159-163 °C |
| Boiling Point: | 555.1 °C at 760 mmHg |
| Flash Point: | 289.5 °C |
| Solubility: | Freely soluble in alcohols or acetone. Also soluble in DMF or chloroform. Insoluble in water |
| Appearance: | White powder. |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 22-36 |
| PSA: | 27.05000 |
| LogP: | 6.45480 |
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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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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 |
- 24155-42-8
1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol
- 22916-47-8
miconazole
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
Conditions
| Conditions | Yield |
|---|---|
| In acetonitrile at 50℃; for 6h; | 100% |
- 112-82-3
hexadecanyl bromide
- 22916-47-8
miconazole
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| In acetonitrile at 70℃; for 12h; | 93% |
| In acetonitrile for 2h; Reflux; | 93% |
Raw Materials
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Miconazole
Chemistry
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:
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.
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.
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. |
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.
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.
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.
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.