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29342-05-0

Basic Information
CAS No.: 29342-05-0
Name: Ciclopirox
Article Data: 12
Molecular Structure:
Molecular Structure of 29342-05-0 (Ciclopirox)
Formula: C12H17NO2
Molecular Weight: 207.272
Synonyms: 2(1H)-Pyridone,6-cyclohexyl-1-hydroxy-4-methyl- (8CI);2(1H)-Pyridinone,6-cyclohexyl-1-hydroxy-4-methyl-;HOE 296b;Penlac;
EINECS: 249-577-2
Density: 1.193 g/cm3
Melting Point: 144 °C
Boiling Point: 350 °C at 760 mmHg
Flash Point: 165.5 °C
Solubility: soluble in methanol, ethanol or chloroform
Appearance: white or light-yellow powder
Hazard Symbols: C,O
Risk Codes: R8; R35; R34; R20
PSA: 42.23000
LogP: 2.44170
Synthetic route

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

29342-05-0

CICLOPIROX

Conditions
ConditionsYield
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
ConditionsYield
With hydrogenchloride In water84%
With hydrogenchloride In water; ethyl acetate84%
924-50-5

Methyl 3,3-dimethylacrylate

2719-27-9

cyclohexanylcarbonyl chloride

29342-05-0

CICLOPIROX

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydroxylamine sulfate
With hydroxylamine sulfate
504-29-0

2-aminopyridine

14818-35-0

4-methyl-6-cyclohexyl02-pyrone

29342-05-0

CICLOPIROX

Conditions
ConditionsYield
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
ConditionsYield
With hydroxylamine

2-methoxy-4-methylpyridine N-oxide

29342-05-0

CICLOPIROX

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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    Product name: Ciclopirox CAS No.:29342-05-0 Molecule Formula:C12H17NO2 Molecule Weight:207.26 Purity: 99% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS SPECIFI

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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