Ciclopirox supplier | CasNO.29342-05-0

Name
Ciclopirox
EINECS 249-577-2
CAS No. 29342-05-0
Article Data12
CAS DataBase
Density 1.193 g/cm³
Solubility soluble in methanol, ethanol or chloroform
Melting Point 144 °C
Formula C₁₂H₁₇NO₂
Boiling Point 350 °C at 760 mmHg
Molecular Weight 207.272
Flash Point 165.5 °C
Transport Information
Appearance white or light-yellow powder
Safety
Risk Codes R8; R35; R34; R20
Molecular Structure
Hazard Symbols C,O
Synonyms 2(1H)-Pyridone,6-cyclohexyl-1-hydroxy-4-methyl- (8CI);2(1H)-Pyridinone,6-cyclohexyl-1-hydroxy-4-methyl-;HOE 296b;Penlac;
PSA 42.23000
LogP 2.44170

Synthetic route

: 2-cyclohexyl-6-methoxy-4-methylpyridine N-oxide

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Stage #1: 2-cyclohexyl-6-methoxy-4-methylpyridine N-oxide With acetyl chloride for 1h; Reflux; Stage #2: With methanol at 20℃;	95%

: 41621-49-2
cyclopirox olamine

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
With hydrogenchloride In water	84%
With hydrogenchloride In water; ethyl acetate	84%

: 924-50-5
Methyl 3,3-dimethylacrylate

: 2719-27-9
cyclohexanylcarbonyl chloride

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Stage #1: Methyl 3,3-dimethylacrylate; cyclohexanylcarbonyl chloride With aluminum (III) chloride In dichloromethane for 3h; Reflux; Stage #2: With hydroxylamine hydrochloride; sodium acetate In methanol; water at 20 - 30℃; for 20h; Stage #3: With sodium hydroxide In methanol; water at 20℃; for 1h;	34%
With hydroxylamine hydrochloride; sodium acetate 2.) water, methanol, 25 deg C, 20 h; Yield given. Multistep reaction;

: 14818-35-0
4-methyl-6-cyclohexyl02-pyrone

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
With 1H-imidazole; hydroxyammonium sulfate at 90℃; for 5h;	11.8 g

: 288-32-4
1H-imidazole

: 14818-35-0
4-methyl-6-cyclohexyl02-pyrone

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
With hydroxylamine sulfate
With hydroxylamine sulfate

: 504-29-0
2-aminopyridine

: 14818-35-0
4-methyl-6-cyclohexyl02-pyrone

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In dichloromethane

: 504-29-0
2-aminopyridine

: 1824-81-3
2-Amino-6-methylpyridine

: 14818-35-0
4-methyl-6-cyclohexyl02-pyrone

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
With hydroxylamine

...Expand

: 2-methoxy-4-methylpyridine N-oxide

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 1-acetoxy-1,2-benziodoxol-3-one; trifluoroacetic acid / water; dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere; Irradiation 2.1: acetyl chloride / 1 h / Reflux 2.2: 20 °C View Scheme

: 100848-70-2
2-methoxy-4-methyl pyridine

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 12 h / 0 - 20 °C 2.1: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 1-acetoxy-1,2-benziodoxol-3-one; trifluoroacetic acid / water; dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere; Irradiation 3.1: acetyl chloride / 1 h / Reflux 3.2: 20 °C View Scheme

: 541-47-9
3-Methylbutenoic acid

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 5 h / Reflux 2.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux 2.2: 20 h / 20 - 30 °C 2.3: 1 h / 20 °C View Scheme

: 98-89-5
Cyclohexanecarboxylic acid

: 29342-05-0
CICLOPIROX

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; thionyl chloride / 3 h / Reflux 2.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux 2.2: 20 h / 20 - 30 °C 2.3: 1 h / 20 °C View Scheme

: 29342-05-0
CICLOPIROX

A: 3-bromo-6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one

B: 5-bromo-6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 0℃; for 6h; Reflux;	A 90% B 5%

: 29342-05-0
CICLOPIROX

: 96-32-2
bromoacetic acid methyl ester

: methyl 2-((6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl)oxy)-acetate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	80%

: 29342-05-0
CICLOPIROX

: 75-03-6
ethyl iodide

: 6-cyclohexyl-1-ethoxy-4-methylpyridin-2(1H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	74%

: 29342-05-0
CICLOPIROX

: 3-chloro-6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one

Conditions

Conditions	Yield
With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 0℃; for 6h; Reflux;	70%

: zinc(II) sulfate heptahydrate

: 29342-05-0
CICLOPIROX

: C36H48N3O6Zn(1-)

Conditions

Conditions	Yield
In aq. phosphate buffer; water for 0.75h; pH=7.4; Sonication;	67.3%

: 29342-05-0
CICLOPIROX

: 258516-84-6
dibenzyloxy-chloromethylphosphoric acid

: dibenzyl (((6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl)oxy)methyl) phosphate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;	67%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h; Concentration;	67%

: 29342-05-0
CICLOPIROX

: 19715-49-2
4-(dimethylamino)benzenesulfonyl chloride

: 6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl 4-(dimethylamino)benzenesulfonate

Conditions

Conditions	Yield
With pyridine at 20℃; for 24h;	67%

: 29342-05-0
CICLOPIROX

: 6-cyclohexyl-1-hydroxy-3-iodo-4-methylpyridin-2(1H)-one

Conditions

Conditions	Yield
With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 0℃; for 6h; Reflux;	63%

: 29342-05-0
CICLOPIROX

: 98-09-9
benzenesulfonyl chloride

: 6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl benzenesulfonate

Conditions

Conditions	Yield
With pyridine at 20℃; for 24h;	19%

: 29342-05-0
CICLOPIROX

: 98-88-4
benzoyl chloride

: 1351572-55-8
1-benzoyloxy 6-cyclohexyl-4-methylpyridine-2(1H)-one

Conditions

Conditions	Yield
With dmap In dichloromethane at 7℃; for 1.5h;

: 29342-05-0
CICLOPIROX

: 229625-50-7
di-tert-butyl chloromethyl phosphate

: di-tert-butyl (((6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl)oxy)methyl) phosphate

Conditions

Conditions	Yield
With sodium hydride at 0 - 20℃; for 2.5h;
With sodium hydride In mineral oil at 0 - 20℃; for 2.5h;

: 29342-05-0
CICLOPIROX

: ((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl phosphate disodium salt

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran 3: sodium cation View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile 3: sodium cation View Scheme
Multi-step reaction with 4 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile 3: sodium carbonate / water; acetonitrile 4: sodium cation View Scheme

: 29342-05-0
CICLOPIROX

: ((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl dihydrogen phosphate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile 3: sodium carbonate / water; acetonitrile View Scheme

: 29342-05-0
CICLOPIROX

: tert-butyl (((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl) hydrogen phosphate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / 2.5 h / 0 - 20 °C 2: sodium carbonate / water; acetonitrile View Scheme

: 29342-05-0
CICLOPIROX

: 6-cyclohexyl-1-hydroxy-4-methyl-1H-pyridine-2-thione

Conditions

Conditions	Yield
With tetraphosphorus decasulfide In toluene at 80℃; for 5h; Inert atmosphere;	700 mg

: 29342-05-0
CICLOPIROX

: 74-88-4
methyl iodide

: 6-cyclohexyl-1-methoxy-4-methyl-1H-pyridin-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	0.15 g

: 29342-05-0
CICLOPIROX

A: ((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl dihydrogen phosphate

B: ((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl phosphate disodium salt

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / mineral oil / 2.5 h / 0 - 20 °C 2: tetrahydrofuran; dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 3 h / 20 °C View Scheme

: 29342-05-0
CICLOPIROX

: ((6-cyclohexyl-4-methylpyridin-1(2H)-yl)oxy)methyl phosphate disodium salt

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / mineral oil / 2.5 h / 0 - 20 °C 2: tetrahydrofuran; dichloromethane / 2 h / 20 °C 3: sodium View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 3 h / 20 °C 3: sodium View Scheme

: 29342-05-0
CICLOPIROX

: 141-43-5
ethanolamine

: 41621-49-2
cyclopirox olamine

Conditions

Conditions	Yield
In ethyl acetate at 50℃; for 0.5h;

Ciclopirox Specification

1. Introduction of Ciclopirox
Ciclopirox is one kind of white or light-yellow powder. It is soluble in methanol, ethanol or chloroform, slightly soluble in DMF or water, slightly soluble in ethyl ether. The IUPAC Name of it is 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2-one. It belongs to Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles. In addition, the Classification Code of it is Anti-Infective Agents; Antifungal; Antifungal Agents.

2. Properties of Ciclopirox
Physical properties about Ciclopirox are:
(1)Melting Point: 144 °C; (2)Density: 1.193 g/cm³; (3)Boiling Point: 350 °C at 760 mmHg; (4)Flash Point: 165.5 °C; (5)Molar Volume: 173.6 cm³; (6)Polarizability: 22.98×10^-24 cm³; (7)Surface Tension: 51.7 dyne/cm; (8)Enthalpy of Vaporization: 68.85 kJ/mol; (9)Vapour Pressure: 2.71E-06 mmHg at 25 °C; (10)log P (octanol-water): 2.730 (none); (11)XLogP3-AA: 2; (12)H-Bond Donor: 1; (13)H-Bond Acceptor: 2; (14)Rotatable Bond Count: 1; (15)Exact Mass: 207.125929; (16)MonoIsotopic Mass: 207.125929; (17)Topological Polar Surface Area: 40.5; (18)Heavy Atom Count: 15; (19)Complexity: 325.

3. Structure Descriptors of Ciclopirox
(1)Canonical SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O
(2)InChI: InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
(3)InChIKey: SCKYRAXSEDYPSA-UHFFFAOYSA-N
(4)Smiles: c1(cc(cc(n1O)C1CCCCC1)C)=O

4. Physical Properties of Ciclopirox

Physical Property	Value	Units	Temp (deg C)	Source
Melting Point	144	deg C		EXP
log P (octanol-water)	2.730	(none)		EST
Atmospheric OH Rate Constant	7.97E-11	cm3/molecule-sec	25	EST

5. Uses of Ciclopirox
Ciclopirox olamine (also called Batrafen, Loprox, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. It can be used as broad spectrum antimycotic agent with some antibacterial activity.

6. Production of Ciclopirox
Cyclohexane carboxylic acid and thionyl chloride reacted to get cyclohexane chloride. It reacts with 3-methyl-2-butenoate (I) in dichloromethane solvent under the action of the three aluminum chloride, stirring 4h, after post-processing, the vacuum collection of 140-145 °C (0.4kPa), may get 5-oxo-3-methyl-5- Ring Hexyl-3-ene acid methyl ester (ciclopirox Division, II), yield 75%. Again, with hydroxylamine hydrochloride, sodium acetate, methanol and water at room temperature, stirring 20h, adding 50% sodium hydroxide and then stirred 1h. Extracted with benzene after cooling, the water phase acidified to Ph = 6. Then ethanol precipitation of crystals recrystallized, you can get Ciclopirox (CAS NO.29342-05-0) , melting point 140 ~ 142 °C, the yield of 48.3%. Finally with the hydroxyl amine salt in dichloromethane, get almost quantitative ciclopirox olamine, melting point 97 ~ 99 °C.

Or MESITYL OXIDE can be used to manufacture Ciclopirox which is showed as follows:

production of Ciclopirox

Product Name

Ciclopirox

Synthetic route

Ciclopirox Specification

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