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23593-75-1

Basic Information
CAS No.: 23593-75-1
Name: Clotrimazole
Molecular Structure:
Molecular Structure of 23593-75-1 (Clotrimazole)
Formula: C22H17ClN2
Molecular Weight: 344.86
Synonyms: Diphenyl(2-chlorophenyl)(1-imidazolyl)methane;Bay-B 5097;BAYb 5097;Mycelex (TN);(2-Chlorophenyl)diphenyl-1-imidazolylmethane;Lotrimin (TN);Clotrimazol [INN-Spanish];Gyne-Lotrimin;1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole;Mycelex Troches;1H-Imidazole, 1-[ (2-chlorophenyl)diphenylmethyl]-;Imidazole, 1- (o-chloro-.alpha.,.alpha.-diphenylbenzyl)-;Bis-fenil-(2-clorofenil)-1-imidazolil-metano [Italian];Lotrimin AF Cream;1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole;Lotrimax;Prestwick_120;FB 5097;Monobaycuten;1-(o-Chloro-.alpha., .alpha.-diphenylbenzyl)imidazole;Trimysten;Bis-phenyl-(2-chlorophenyl)-1-imidazoyl)methane;BAY b5097;Mykosporin;Mycelex G;
EINECS: 245-764-8
Density: 1.13 g/cm3
Melting Point: 147-149 °C
Boiling Point: 482.3 °C at 760 mmHg
Flash Point: 245.5 °C
Solubility: <10mg/L(25 oC)
Appearance: Crystalline
Hazard Symbols: IrritantXi
Risk Codes: 22-36/38
Safety: 26-36
Transport Information:
PSA: 17.82000
LogP: 5.37670
Synthetic route
288-32-4

1H-imidazole

102-10-3

diphenyl phosphite

66774-02-5

o-chlorotriphenylmethanol

108-10-1

4-methyl-2-pentanone

23593-75-1

clotrimazole

Conditions
ConditionsYield
With sodium hydroxide100%
With sodium hydroxide77%
288-32-4

1H-imidazole

42074-68-0

2-chlorotrityl chloride

23593-75-1

clotrimazole

Conditions
ConditionsYield
With sodium carbonate at 25℃; for 48h; Reagent/catalyst; Solvent; Concentration; Green chemistry;92%
With sodium carbonate at 20℃; for 48h; Sealed tube;92%
With triethylamine In acetonitrile Heating;
With triethylamine In toluene at 20 - 50℃; for 3h; Temperature; Solvent; Inert atmosphere;
288-32-4

1H-imidazole

102-10-3

diphenyl phosphite

66774-02-5

o-chlorotriphenylmethanol

23593-75-1

clotrimazole

Conditions
ConditionsYield
In toluene74.5%
In acetonitrile; benzene73%
66774-02-5

o-chlorotriphenylmethanol

23593-75-1

clotrimazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / Heating
2: triethylamine / acetonitrile / Heating
View Scheme
23593-75-1

clotrimazole

150994-84-6

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

4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobutanoate 1-((2-chlorophenyl)diphenylmethyl)-1H-imidazol-3-ium

Conditions
ConditionsYield
In acetonitrile at 50℃; for 6h;100%
23593-75-1

clotrimazole

66774-02-5

o-chlorotriphenylmethanol

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;93%
With hydrogenchloride; water for 3h; Heating / reflux;85%
With hydrogenchloride In water; isopropyl alcohol for 17h; Heating;36%
17084-13-8

potassium hexafluorophosphate

cis-{Ru(Bipy)(Dppe)Cl2}

23593-75-1

clotrimazole

[RuCl(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)(1,2-bis(diphenylphosphino)ethane)(2,2′-bypiridine)]*hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium hexafluorophosphate; cis-{Ru(Bipy)(Dppe)Cl2} In dichloromethane for 1h; Inert atmosphere;
Stage #2: clotrimazole In dichloromethane for 6h; Reflux; Inert atmosphere;
92%
23593-75-1

clotrimazole

C22H14(2)H3ClN2

Conditions
ConditionsYield
With deuteromethanol; di(tertbutyl)phenylphosphine; silver carbonate at 65℃; for 48h; Inert atmosphere;91%
23593-75-1

clotrimazole

141776-91-2

1-bromomethyl-3,5-difluoro-benzene

3-[(2-chloro-phenyl)-diphenyl-methyl]-1-(3,5-difluoro-benzyl)-3H-imidazol-1-ium; bromide

Conditions
ConditionsYield
In ethyl acetate for 48h; Heating;90%
17084-13-8

potassium hexafluorophosphate

200358-34-5, 200259-33-2

dichloro[1,4-bis(diphenylphosphino)butane](2,2'-bipyridine)ruthenium(II)

23593-75-1

clotrimazole

[RuCl(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)(1,4-bis(diphenylphosphino)butane)(2,2′-bypiridine)]*hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium hexafluorophosphate; dichloro[1,4-bis(diphenylphosphino)butane](2,2'-bipyridine)ruthenium(II) In dichloromethane for 1h; Inert atmosphere;
Stage #2: clotrimazole In dichloromethane for 6h; Reflux; Inert atmosphere;
90%
52490-94-5

[dichloro(p-cymene)(triphenylphosphane)ruthenium(II)]

23593-75-1

clotrimazole

hexafluorophosphate salt

hexafluorophosphate salt

[RuCl(clotrimazole)(η6-p-cymene)(PPh3)]PF6

Conditions
ConditionsYield
In methanol for 8h; Reflux; Inert atmosphere;90%
6046-93-1

copper(II) acetate monohydrate

23593-75-1

clotrimazole

[Cu(clotrimazole)2(Ac)2]*H2O

Conditions
ConditionsYield
In methanol at 25℃; for 24h;90%

[RhCl2(p-cymene)]2

23593-75-1

clotrimazole

1581279-26-6

[(η6-p-cymene)RuCl(clotrimazole)2]Cl

Conditions
ConditionsYield
In methanol; chloroform for 5h; Reflux;89%
26042-63-7

silver(I) hexafluorophosphate

[RhCl2(p-cymene)]2

23593-75-1

clotrimazole

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

Conditions
ConditionsYield
In methanol; chloroform for 3h; Reflux;86%
17084-13-8

potassium hexafluorophosphate

cis-[RuCl2(1,1′-bis(diphenylphosphino)ferrocene)(2,2′-bipyridine)]

23593-75-1

clotrimazole

[RuCl(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)(1,1′-bis(diphenylphosphino)ferrocene)(2,2′-bypiridine)]*hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium hexafluorophosphate; cis-[RuCl2(1,1′-bis(diphenylphosphino)ferrocene)(2,2′-bipyridine)] In dichloromethane for 1h; Inert atmosphere;
Stage #2: clotrimazole In dichloromethane for 6h; Reflux; Inert atmosphere;
86%

copper(II) nitrate trihydrate

23593-75-1

clotrimazole

[Cu(clotrimazole)2(H2O)(NO3)](NO3)*2H2O

Conditions
ConditionsYield
In methanol at 25℃; for 24h;84%
23593-75-1

clotrimazole

519-73-3

triphenylmethane

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 24h; Electrolysis; Green chemistry;81%
12092-47-6

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

23593-75-1

clotrimazole

209979-92-0

RhCl(1,5-cyclooctadiene)(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)

Conditions
ConditionsYield
In ethanol N2-atmosphere; stoich. amts., stirring at room temp. for 1 h; collection (filtration), washing (MeOH), drying (vac.); elem. anal.;80%
23593-75-1

clotrimazole

1605347-53-2

4-chloro-1-((2-chlorophenyl)diphenylmethyl)-1H-imidazole

Conditions
ConditionsYield
With N-chloro-N-fluoro-benzenesulfonamide In acetonitrile at 20℃; Reagent/catalyst;80%
With N-chloro-N-fluoro-benzenesulfonamide In acetonitrile at 20℃; regioselective reaction;77%
With 2-chloro-1,3-bis(methoxycarbonyl)guanidine In chloroform at 20℃; for 12h; Solvent; regioselective reaction;72%
23593-75-1

clotrimazole

2550-36-9

(bromomethylcyclohexane)

3-[(2-chloro-phenyl)-diphenyl-methyl]-1-cyclohexylmethyl-3H-imidazol-1-ium; bromide

Conditions
ConditionsYield
In ethyl acetate for 48h; Heating;79%
14494-93-0, 23751-62-4, 106678-35-7

bis(triphenylphosphino)copper(I) nitrate

23593-75-1

clotrimazole

[Cu(PPh3)2(1-[(2-chlorophenyl)-diphenylmethyl]-1H-imidazole)2]NO3

Conditions
ConditionsYield
In acetonitrile for 24h;79%

C14H20B9(1-)*C4H12N(1+)

23593-75-1

clotrimazole

C36H36B9ClN2

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dimethoxyethane at 20℃; for 5h; Inert atmosphere; Schlenk technique;78%
23593-75-1

clotrimazole

7646-85-7

zinc(II) chloride

[ZnCl2(N2C3H3C(C6H5)2C6H4Cl)2(H2O)2]*3H2O

Conditions
ConditionsYield
In ethanol; water hot soln. (60 °C) of metal chloride added to hot soln. (60 °C) of CLMZ, mixt. stirred under reflux for 1 h; pptn., filtration, washing (ethanol/water, petroleum ether), elem. anal.;77%
23593-75-1

clotrimazole

C22H16BrClN2

Conditions
ConditionsYield
With N-chloro-N-fluoro-benzenesulfonamide; potassium bromide In acetonitrile at 20℃; for 0.25h;77%
23593-75-1

clotrimazole

74-88-4

methyl iodide

3-[(2-chloro-phenyl)-diphenyl-methyl]-1-methyl-3H-imidazol-1-ium; iodide

Conditions
ConditionsYield
In dichloromethane at 45℃; for 0.25h; Microwave irradiation;75%
In ethyl acetate at 20℃; for 48h;49%
64443-05-6

tetrakis(actonitrile)copper(I) hexafluorophosphate

23593-75-1

clotrimazole

[Cu(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)2]PF6

Conditions
ConditionsYield
In dichloromethane stoich. amts., room temp., 24 h; vol. reduction (N2-stream), Et2O addn., cooling to -5°C (pptn.), collection (filtration), washing (Et2O), drying (vac.); elem. anal.;75%

manganese(II) chloride dihydrate

23593-75-1

clotrimazole

1311268-76-4

[MnCl2(N2C3H3C(C6H5)2C6H4Cl)2(H2O)2]

Conditions
ConditionsYield
In ethanol; water hot soln. (60 °C) of metal chloride added to hot soln. (60 °C) of CLMZ, mixt. stirred under reflux for 1 h; pptn., filtration, washing (ethanol/water, petroleum ether), elem. anal.;75%

[RhCl2(p-cymene)]2

23593-75-1

clotrimazole

[(η6-p-cymene)RuCl2(clotrimazole)]

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 0.075h; Reflux;75%

zinc(II) nitrate hexahydrate

23593-75-1

clotrimazole

[Zn(clotrimazole)2(H2O)(NO3)](NO3)*4H2O

Conditions
ConditionsYield
In methanol at 25℃; for 0.5h;74%
23593-75-1

clotrimazole

C22H13(2)H4ClN2

Conditions
ConditionsYield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;73%
Downstream Products
66774-02-5
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    Clotrimazole

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    Clotrimazole

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    Product Name:Clotrimazole Molecular Formula:C22H17ClN2 Molecular Weight:344.84 CAS No.:23593-75-1 EINECS:245-764-8 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:drum Application:Genito-Urinary Tra

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    Factory supply 99% clotrimazole crystalline in stock

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Chemistry

Molecular Structure:

Molecular Formula: C22H17ClN2
Molecular Weight: 344.8368
IUPAC Name: 1-[(2-Chlorophenyl)-diphenylmethyl]imidazole
Synonyms of Mycosporin (CAS NO.23593-75-1): Clotrimazole ; Clotrimazole [USAN:INN:BAN:JAN] ; Lotrimax ; Lotrisone ; Otomax (Veterinary) ; 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI) ; 1H-Imidazole, 1-((2-chlorophenyl)diphenylmethyl)- ; Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-
CAS NO: 23593-75-1
Classification Code: Anti-Infective Agents ; Anti-infective agents, local ; Antifungal ; Antifungal agents ; Drug / Therapeutic Agent ; Human Data ; Reproductive Effect
Melting Point: 147-149°C 
Index of Refraction: 1.616
Molar Refractivity: 105.88 cm3
Molar Volume: 302.7 cm3
Surface Tension: 44.5 dyne/cm
Density: 1.13 g/cm3
Flash Point: 245.5 °C
Enthalpy of Vaporization: 71.87 kJ/mol
Boiling Point: 482.3 °C at 760 mmHg
Vapour Pressure: 5.42E-09 mmHg at 25°C

Uses

 Mycosporin (CAS NO.23593-75-1) is a kind of broad-spectrum antifungals.

Production

 o-Chlorobenzoic acid could be used as a raw material to synthesize Mycosporin (CAS NO.23593-75-1)

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
dog LD50 oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mammal (species unspecified) LD50 oral 750mg/kg (750mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 271, 1969.
mouse LD50 intraperitoneal 108mg/kg (108mg/kg)   Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
mouse LD50 intravenous 198mg/kg (198mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral 761mg/kg (761mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mouse LDLo subcutaneous 10gm/kg (10000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
rabbit LD50 oral > 1gm/kg (1000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LD50 intraperitoneal 445mg/kg (445mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
rat LD50 oral 708mg/kg (708mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LDLo subcutaneous 10gm/kg (10000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
women TDLo intravaginal 28mg/kg/7D (28mg/kg) SKIN AND APPENDAGES (SKIN): PRIMARY IRRITATION: AFTER TOPICAL EXPOSURE Clinical Toxicology. Vol. 18, Pg. 41, 1981.

Safety Profile

Safety Information of Mycosporin (CAS NO.23593-75-1):
Hazard Codes:Xn 
Risk Statements:22-36/38
22:Harmful if swallowed
36/38:Irritating to eyes and skin  
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:Wear suitable protective clothing 
WGK Germany:3
RTECS:NI4377000
Hazardous Substances Data:23593-75-1(Hazardous Substances Data)
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Human systemic effects by intrvaginal route: primary skin irritations. Experimental reproductive effects. A fungicide. When heated to decomposition it emits very toxic fumes of Cl and NOx.