MICONAZOLE supplier | CasNO.22916-47-8

Name
Miconazole
EINECS 245-324-5
CAS No. 22916-47-8
Article Data6
CAS DataBase
Density 1.4 g/cm³
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
Appearance White powder.
Safety 22-36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
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;
PSA 27.05000
LogP 6.45480

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

: 2,4-dichlorobenzyl methanesulfonate

: 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

: 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

Conditions	Yield
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

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%

: silver perchlorate

: 22916-47-8
miconazole

: [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2ClO4]

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	92%
In ethanol; water at 20℃; for 24h;	82%

: 111-25-1
1-bromo-hexane

: 22916-47-8
miconazole

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

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 12h;	90%

: 143-15-7
1-dodecylbromide

: 22916-47-8
miconazole

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

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 12h;	90%

: chromium(III) nitrate nonahydrate

: 22916-47-8
miconazole

: C18H14Cl4CrN5O10

Conditions

Conditions	Yield
In methanol for 3h; Reflux;	86.96%

: 141776-91-2
1-bromomethyl-3,5-difluoro-benzene

: 22916-47-8
miconazole

: 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,5-difluoro-benzyl)-3H-imidazol-1-ium; bromide

Conditions

Conditions	Yield
In ethyl acetate for 48h; Heating;	86%

: 112-29-8
1-bromo dodecane

: 22916-47-8
miconazole

: 57264-60-5
3-decyl-1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazol-3-ium bromide

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 12h;	85%

: copper(II) choride dihydrate

: 22916-47-8
miconazole

: [Cu(II)Cl2(miconazol)2(water)2]*2water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of copper compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	85%

: 112-71-0
1-Bromotetradecane

: 22916-47-8
miconazole

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

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 12h;	85%

: 26042-63-7
silver(I) hexafluorophosphate

: [RhCl2(p-cymene)]2

: 22916-47-8
miconazole

: [(η6-p-cymene)Ru(miconazole)3](PF6)2

Conditions

Conditions	Yield
In methanol; chloroform for 3h; Reflux;	83%

...Expand

: silver nitrate

: 22916-47-8
miconazole

: [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2NO3]

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 24h;	82%

: 14104-20-2
silver tetrafluoroborate

: 22916-47-8
miconazole

: [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2BF4]

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 24h;	82%

: zinc(II) chloride dihydrate

: 22916-47-8
miconazole

: [Zn(II)Cl2(miconazol)2(water)2]*3water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of zinc compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	80%

: silver nitrate

: 22916-47-8
miconazole

: [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2NO3]

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	80%

: [RhCl2(p-cymene)]2

: 22916-47-8
miconazole

: 1581279-28-8
[(η6-p-cymene)RuCl(miconazole)2]Cl

Conditions

Conditions	Yield
In methanol; chloroform for 5h; Reflux;	77%

: manganese(II) chloride dihydrate

: 22916-47-8
miconazole

: 1410795-51-5
[Mn(II)Cl2(miconazol)2(water)2]*water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of manganese compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	75%

: C14H20B9(1-)*C4H12N(1+)

: 22916-47-8
miconazole

: C32H33B9Cl4N2O

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dimethoxyethane at 20℃; for 5h; Inert atmosphere; Schlenk technique;	73%

: 22916-47-8
miconazole

: 74-88-4
methyl iodide

: 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-methyl-1H-imidazol-3-ium iodide

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 12h;	71%
In ethyl acetate at 20℃; for 48h;	69%
Heating; Yield given;

: [RhCl2(p-cymene)]2

: 22916-47-8
miconazole

: [(η6-p-cymene)RuCl2(miconazole)]

Conditions

Conditions	Yield
In methanol; chloroform at 20℃; for 0.075h; Reflux;	71%

: chromium chloride hexahydrate

: 22916-47-8
miconazole

: [Cr(III)Cl2(miconazol)2(water)2]Cl*3water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of chromium compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	70%

: cobalt(II) chloride hexahydrate

: 22916-47-8
miconazole

: [Co(II)Cl2(miconazol)2(water)2]*2water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of cobalt compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	68%

: iron(III) chloride hexahydrate

: 22916-47-8
miconazole

: [Fe(III)Cl2(miconazol)2(water)2]Cl*3water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of iron compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	65%

: [Ru(p-cymene)Cl2]2

: 22916-47-8
miconazole

: [(η6-p-cymene)RuCl2(miconazole)]

Conditions

Conditions	Yield
In acetone for 20h; Inert atmosphere; Schlenk technique;	65%

: silver hexafluoroantimonate

: 22916-47-8
miconazole

: [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2SbF6]

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 24h;	65%

: nickel(II) chloride hexahydrate

: 22916-47-8
miconazole

: [Ni(II)Cl2(miconazol)2(water)2]*3water

Conditions

Conditions	Yield
In ethanol; water addn. of hot soln. of nickel compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	60%

: 2043-57-4
1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane

: 22916-47-8
miconazole

: 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-3H-imidazol-1-ium; iodide

Conditions

Conditions	Yield
In tetrahydrofuran Heating;	52%

: ammonium hexafluorophosphate

: MnBr(bpyCOOCH3,COOCH3)(CO)3

: 22916-47-8
miconazole

: [Mn(bpyCOOCH3,COOCH3)(CO)3(miconazole)]PF6

Conditions

Conditions	Yield
Stage #1: MnBr(bpyCOOCH3,COOCH3)(CO)3 With silver trifluoromethanesulfonate In acetone at 20℃; for 3h; Darkness; Inert atmosphere; Schlenk technique; Stage #2: miconazole at 20℃; for 20h; Schlenk technique; Inert atmosphere; Darkness; Stage #3: ammonium hexafluorophosphate In methanol; water Schlenk technique; Inert atmosphere; Darkness;	49%

...Expand

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 NO_x.

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.

Product Name

Miconazole

Synthetic route

MICONAZOLE Chemical Properties

MICONAZOLE Uses

MICONAZOLE Toxicity Data With Reference

MICONAZOLE Safety Profile

MICONAZOLE Specification

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