61397-58-8

Basic information

• Product Name: KETOCONAZOLE INTERMEDIATE
• Synonyms: KETOCONAZOLE INTERMEDIATE;cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol;[(R)-2-(2,4-DICHLORO-PHENYL)-2-IMIDAZOL-1-YLMETHYL-[1,3]DIOXOLAN-4-YL]-METHANOL;CIS-2-(2,4-DICHLOROPHENYL)-2- (1H-IMIDAZOL-1-YLMETHYL)-1,3;rel-2α*-(1H-Imidazole-1-ylmethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4α*-methanol;(2R,4S)-rel-2-(2,4-dichlorophenyl)-2-(1H-iMidazol-1-ylMethyl)-1,3-dioxolane-4-Methanol;1,3-Dioxolane-4-Methanol, 2-(2,4-dichlorophenyl)-2-(1H-iMidazol-1-ylMethyl)-, cis-;Ketoconazole Impurity 8 (rac-Ketoconazole Hydroxymethyl Impurity)
• CAS NO: 61397-58-8
• Molecular Formula: C₁₄H₁₄Cl₂N₂O₃
• Molecular Weight: 329.17856
• EINECS: 262-766-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 61397-58-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 99-101 °C
• Boiling Point: 529.1°C at 760 mmHg
• Flash Point: 273.8°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 5.06E-12mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.20±0.10(Predicted)
• CAS DataBase Reference: KETOCONAZOLE INTERMEDIATE(CAS DataBase Reference)
• NIST Chemistry Reference: KETOCONAZOLE INTERMEDIATE(61397-58-8)
• EPA Substance Registry System: KETOCONAZOLE INTERMEDIATE(61397-58-8)

Safety Data

• Hazardous Substances Data: 61397-58-8(Hazardous Substances Data)

Usage

Description

KETOCONAZOLE INTERMEDIATE, also known as cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol, is a chemical intermediate used in the synthesis of Ketoconazole, an antifungal medication. It possesses modulatory activity on the large conductance calcium-activated potassium channel (BKCa), which may contribute to its therapeutic effects.

Uses

Used in Pharmaceutical Industry:
KETOCONAZOLE INTERMEDIATE is used as a chemical intermediate for the synthesis of Ketoconazole, an antifungal agent. It is utilized in the development of medications that target fungal infections, particularly those caused by dermatophytes, yeasts, and other pathogenic fungi.
Used in Research Applications:
KETOCONAZOLE INTERMEDIATE is also used in research settings to study the modulatory effects on the large conductance calcium-activated potassium channel (BKCa). This research can contribute to a better understanding of the underlying mechanisms of action of Ketoconazole and its potential applications in various therapeutic areas.

InChI:InChI=1/C14H14Cl2N2O3/c15-10-1-2-12(13(16)5-10)14(8-18-4-3-17-9-18)20-7-11(6-19)21-14/h1-5,9,11,19H,6-8H2/t11-,14-/m1/s1

Upstream product

• 83086-42-4 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester; compound with nitric acid 
• 70894-66-5 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 68751-57-5 2-(2,4-dichlorophenyl)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane 
• 172032-21-2 (2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methanol 
• 61397-56-6 (+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 83086-42-4 Benzoic acid (2R,4S)-2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester; compound with nitric acid 

Downstream Products

• 61397-61-3 cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-(1,3-dioxolan-4-yl)]methyl methanesulfonate 
• 61397-61-3 trans-<2-(2,4-Dichlorophenyl)-2-<1H-imidazol-1-yl>methyl-(1,3-dioxolan-4-yl)>methyl methanesulfonate 
• 85650-50-6 cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate 
• 59363-98-3 1-[(2R,4S)-2-(2,4-Dichloro-phenyl)-4-phenoxymethyl-[1,3]dioxolan-2-ylmethyl]-1H-imidazole 

Relevant articles and documents

Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)- 1,3-dioxolanes

A series of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1,3-dioxolanes Ia-u was synthesized and tested in vitro against pathogenic fungi in man, animals and plants: Candida albicans, Aspergillus flavus and Fusarium solani. Compounds Iq-t with two polyazol groups have an in vitro activity against these fungi with MIC (minimum inhibitory concentration) value of 5 μg mL-1.