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Basic Information
CAS No.: 22832-87-7
Name: Miconazole nitrate
Article Data: 1
Molecular Structure:
Molecular Structure of 22832-87-7 (Miconazole nitrate)
Formula: C18H15Cl4N3O4
Molecular Weight: 479.147
Synonyms: 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole; nitric acid;Conofite;[2,4-Dichloro-.beta.-(2, 4-dichlorobenzyloxy)phenethyl]imidazole nitrate;1H-Imidazole,1-[2-(2,4-dichlorophenyl)-2- [(2,4-dichlorophenyl)methoxy]ethyl]-,mononitrate;Gyno-Monistat;Micatin;Imidazole, 1-[2,4-dichloro-.beta.-[ (2, 4-dichlorobenzyl)oxy]phenethyl]-, mononitrate;Florid;1H-Imidazole, 1-[2- (2,4-dichlorophenyl)-2-[(2, 4-dichlorophenyl)methoxy]ethyl]-, mononitrate;Daktarin;Aflorix;Miconazol Nitrate;
EINECS: 245-256-6
Density: 1.451g/cm3
Melting Point: 170-185 °C
Boiling Point: 555.1 °C at 760 mmHg
Flash Point: 289.5 °C
Solubility: Slightly soluble in water. Soluble in propylene glycol or pyridine.
Appearance: White crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-43-40
Safety: 36/37
PSA: 93.10000
LogP: 6.63030
Synthetic route
22832-87-7

miconasole nitrate

71-43-2

benzene

61023-62-9

1-[β-(2,4-dichlorophenyl)-phenethyl]imidazole

Conditions
ConditionsYield
Stage #1: miconasole nitrate With sodium hydroxide In chloroform
Stage #2: benzene With trifluorormethanesulfonic acid In chloroform at 25℃; for 4h; Friedel Crafts alkylation;
65%
22832-87-7

miconasole nitrate

A

1777-82-8

(2,4-dichlorophenyl)methanol

B

50-84-0

2,4 dichlorobenzoic acid

C

874-42-0

2,4-dichlorobenzaldeyhde

D

61258-52-4

1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethanol; compound with nitric acid

E

68601-96-7

1-[2,4-dichloro-β-(2,4-dichlorophenylcarbonyloxy)phenethyl]-imidazole nitrate

F

1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-imidazolidine-2,4,5-trione; compound with nitric acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); oxygen In ethanol at 77.5℃; under 5171.5 Torr; for 3.4h; Product distribution; Mechanism; other times;A 0.2 % Chromat.
B 0.7 % Chromat.
C 1.3 % Chromat.
D 0.9 % Chromat.
E 2.3 % Chromat.
F 0.3 % Chromat.
22832-87-7

miconasole nitrate

A

50-84-0

2,4 dichlorobenzoic acid

B

874-42-0

2,4-dichlorobenzaldeyhde

C

61258-52-4

1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethanol; compound with nitric acid

D

68601-96-7

1-[2,4-dichloro-β-(2,4-dichlorophenylcarbonyloxy)phenethyl]-imidazole nitrate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); oxygen In ethanol at 77.5℃; under 5171.5 Torr; for 3.4h; Further byproducts given;A 0.7 % Chromat.
B 1.3 % Chromat.
C 0.9 % Chromat.
D 2.3 % Chromat.
22832-87-7

miconasole nitrate

A

N-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-formamide

B

N-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-oxalamide

C

1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-imidazolidine-2,4,5-trione

D

68601-95-6

1-(2,4-dichloro-benzoyloxy)-1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethane

Conditions
ConditionsYield
With sodium hydroxide; 2,2'-azobis(isobutyronitrile); oxygen In ethanol at 111℃; under 10343 Torr; for 3.3h; Further byproducts given;
22832-87-7

miconasole nitrate

A

2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl-cyanamide

B

N-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-oxalamide

C

1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-imidazolidine-2,4,5-trione

D

68601-95-6

1-(2,4-dichloro-benzoyloxy)-1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethane

Conditions
ConditionsYield
With sodium hydroxide; 2,2'-azobis(isobutyronitrile); oxygen In ethanol at 111℃; under 10343 Torr; for 3.3h; Further byproducts given;
22832-87-7

miconasole nitrate

A

[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-urea

B

N-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-oxalamide

C

1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-imidazolidine-2,4,5-trione

D

68601-95-6

1-(2,4-dichloro-benzoyloxy)-1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethane

Conditions
ConditionsYield
With sodium hydroxide; 2,2'-azobis(isobutyronitrile); oxygen In ethanol at 111℃; under 10343 Torr; for 3.3h; Further byproducts given;
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

22832-87-7

miconasole nitrate

2,6-di-tert-butyl-4-methylphenol-miconazole adduct

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Specification

The Miconazole nitrate, with the CAS registry number 22832-87-7, is also known as 1-(2,4-Dichloro-beta-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole nitrate. It belongs to the product categories of Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals.This chemical's molecular formula is C18H14Cl4N2O.HNO3 and molecular weight is 479.15. What's more,Its systematic name is Miconazole nitrate.It is a White Solid.And it is an imidazole antifungal agent that is used topically and by intravenous infusion. Inhibits lanosterol demethylase and induces formation of reactive oxygen species.The Miconazole nitrate is harmful if swallowed .There is limited evidence of a carcinogenic effect. It may cause sensitization by skin contact .When you use it, wear suitable protective clothing and gloves.

Physical properties about Methyltrimethoxysilane are:
(1)ACD/LogP:  5.932; (2)# of Rule of 5 Violations:  1; (3)ACD/LogD (pH 5.5):  4.76; (4)ACD/LogD (pH 7.4):  5.86; (5)ACD/BCF (pH 5.5):  1289.42; (6)ACD/BCF (pH 7.4):  16071.52; (7)ACD/KOC (pH 5.5):  2729.93; (8)ACD/KOC (pH 7.4):  34026.25; (9)#H bond acceptors:  3; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  6; (12)Flash Point:  289.5 °C; (13)Enthalpy of Vaporization:  80.52 kJ/mol ; (14)Boiling Point:  555.1 °C at 760 mmHg; (15)Vapour Pressure:  8.55E-12 mmHg at 25°C;

You can still convert the following datas into molecular structure:
(1)SMILES:[O-][N+](=O)O.Clc1ccc(c(Cl)c1)C(OCc2ccc(Cl)cc2Cl)Cn3ccnc3;
(2)Std. InChI:InChI=1S/C18H14Cl4N2O.HNO3/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4);
(3)Std. InChIKey:MCCACAIVAXEFAL-UHFFFAOYSA-N.

The toxicity data of Miconazole nitrate as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 160mg/kg (160mg/kg)   Chemotherapy Vol. 17(6), Pg. 392, 1972.
guinea pig LD50 oral 276mg/kg (276mg/kg)   Chemotherapy Vol. 17(6), Pg. 392, 1972.
mouse LD50 intraperitoneal 480mg/kg (480mg/kg)   Drugs in Japan Vol. 6, Pg. 809, 1982.
mouse LD50 intravenous 28mg/kg (28mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
mouse LD50 oral 578mg/kg (578mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Chemotherapy Vol. 17(6), Pg. 392, 1972.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 353, 1976.
rat LD50 intraperitoneal 1060mg/kg (1060mg/kg)   Drugs in Japan Vol. 6, Pg. 809, 1982.
rat LD50 intravenous 14700ug/kg (14.7mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 oral 920mg/kg (920mg/kg)   Drugs in Japan Vol. 6, Pg. 809, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 353, 1976.