79156-75-5

Basic information

• Product Name: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
• Synonyms: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone;Nsc317629;1-[4-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone;1-[4-[4-[[2-(2;3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone;4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1
• CAS NO: 79156-75-5
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₄
• Molecular Weight: 531.4309
• EINECS: 265-667-4
• Mol File: 79156-75-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 146℃
• Boiling Point: 753.4 °C at 760 mmHg
• Flash Point: 409.4 °C
• Appearance: /
• Density: 1.38
• Vapor Pressure: 1.39E-22mmHg at 25°C
• Refractive Index: 1.642
• PKA: 6.88±0.12(Predicted)
• CAS DataBase Reference: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone(79156-75-5)
• EPA Substance Registry System: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone(79156-75-5)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R25:
• Safety Statements: S36:; S45:
• Hazardous Substances Data: 79156-75-5(Hazardous Substances Data)

Usage

Description

1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone is a complex organic molecule characterized by a piperazine ring and a variety of functional groups. It features two phenyl rings, a dioxolane ring, an imidazole ring, and an ethanone group, along with chlorine atoms that may influence its reactivity and biological effects. The presence of the imidazole group suggests potential pharmaceutical applications, as imidazole-containing compounds are known for their biological activity. The intricate structure and combination of these functional groups indicate that this chemical may possess a range of chemical and biological properties.

Uses

Used in Pharmaceutical Industry:
1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone is used as a pharmaceutical compound for its potential biological activity. The presence of the imidazole ring, which is common in various drugs, suggests that this molecule could be utilized in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone serves as a subject for studying the effects of its complex structure and functional groups on chemical reactivity and stability. Researchers may explore its potential interactions with other molecules and its use in the synthesis of new compounds with specific properties.
Used in Material Science:
1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone may also find applications in material science, where its unique structure could be leveraged to create new materials with tailored properties. For instance, its potential use in the development of advanced polymers, coatings, or sensors could be investigated based on its chemical and physical characteristics.

InChI:InChI=1/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23?,26-/m0/s1

Upstream product

• 65277-42-1 ketoconazole 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 82966-35-6 (2S,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-1,3-dioxolane 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 170210-49-8 cis-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-4-hydroxymethyl-1,3-dioxolane 
• 170210-50-1 (2S,4S)-(i)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl methanesulfonate 
• 67914-60-7 N-acetyl-N'-(4-hydroxyphenyl)piperazine 
• 288-32-4 1H-imidazole 
• 142128-65-2 (2S,4R)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane 
• 38869-47-5 4-(p-methoxyphenyl)piperazine dihydrochloride 
• 133345-21-8 1-(4-Acetoxyphenyl)-4-acetylpiperazine 
• 38869-37-3 1-(4-hydroxy-phenyl)-piperazine dihydrobromide 
• 61397-61-3 trans-<2-(2,4-Dichlorophenyl)-2-<1H-imidazol-1-yl>methyl-(1,3-dioxolan-4-yl)>methyl methanesulfonate 
• 345649-43-6 (2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate 

Downstream Products

• 65277-42-1 ketoconazole 
• 142128-58-3 (2R,4R)-Ketoconazole 
• 65277-42-1 ketoconazole 
• 142128-60-7 (2S,4S)-Ketoconazole 
• 1621914-69-9 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-difluoromethanesulfonylpiperazine 
• 1621914-58-6 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-trifluoromethanesulfonylpiperazine 
• 1621914-75-7 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(oxane-4-sulfonyl)piperazine 
• 1621914-73-5 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(2-methoxyethanesulfonyl)piperazine 
• 1621914-36-0 1-(cyclopropanesulfonyl)-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine 
• 1621914-35-9 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propane-2-sulfonyl)piperazine 
• 1621914-34-8 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(ethanesulfonyl)piperazine 
• 1621914-65-5 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(1-methylimidazol-2-ylsulfonyl)piperazine 
• 1621914-63-3 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(thiophene-2-sulfonyl)piperazine 
• 1621914-66-6 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-methanesulfonylmethanesulfonylpiperazine 

Relevant articles and documents

Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds

The graphene oxide (GO) was covalently coupled to the surfaces of silica gel (SiO2) microspheres by amide bond to get the graphene oxide@silica gel (GO@SiO2). Then, the GO@SiO2 was reduced with hydrazine to the reduced graphene oxide@silica gel (rGO@SiO2), and the cellulose derivatives were physically coated on the surfaces of rGO@SiO2 to prepare a chiral stationary phase (CSP) for high performance liquid chromatography. Under the optimum experimental conditions, eight benzene-enriched enantiomers were separated completely, and the resolution of trans-stilbene oxide perfectly reached 4.83. Compared with the blank column of non-bonded rGO, the separation performance is better on the new CSP, which is due to the existence of rGO to produce special retention interaction with analytes, such as π-π stacking, hydrophobic effect, π-π electron-donor–acceptor interaction, and hydrogen bonding. Therefore, the obtained CSP shows special selectivity for benzene-enriched enantiomers, improves separation selectivity and efficiency, and rGO plays a synergistic effect with cellulose derivatives on enantioseparation.

Chiral separation of four stereoisomers of ketoconazole drugs using capillary electrophoresis

This work aimed to develop a chiral separation method of ketoconazole enantiomers using electrokinetic chromatography. The separation was achieved using heptakis (2, 3, 6- tri-O-methyl)-β-cyclodextrin (TMβCD), a commonly used chiral selector (CS), as it is relatively inexpensive and has a low UV absorbance in addition to an anionic surfactant, sodium dodecyl sulfate (SDS). The influence of TMβCD concentration, phosphate buffer concentration, SDS concentration, buffer pH, and applied voltage were investigated. The optimum conditions for chiral separation of ketoconazole was achieved using 10mM phosphate buffer at pH2.5 containing 20mM TMβCD, 5mM SDS, and 1.0% (v/v) methanol with an applied voltage of 25 kV at 25 °C with a 5-s injection time (hydrodynamic injection). The four ketoconazole stereoisomers were successfully resolved for the first time within 17 min (total analysis time was 28 min including capillary conditioning). The migration time precision of this method was examined to give repeatability and reproducibility with RSDs ≤5.80% (n =3) and RSDs ≤8.88% (n =9), respectively.

Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin

Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)- or (S)-epichlorohydrin has been developed.The key-step of syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-14a and (2R,4R)-15a or of their enentiomers, followed by crystalization of the corresponding cis-benzoates, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1.The ee's of (+)- and (-)-ketocanazole were determined by HPLC on the CSP Chiracel OD-H.