74852-61-2

Basic information

• Product Name: 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine
• Synonyms: 1-(4-METHYLOXY-PHENYL)-4-(4-NITRO-PHENYL)-PIPERAZINE;1-(4-METHOXYPHENYL)-4-(4-NITROPHENYL)PIPERAZINE;1-(4-Methoxyphonyl)-4-(4-Nitrophenyl)Piperazine;PIPERAZINE,1-(4-METHOXYPHENYL)-4-(4-NITROPHENYL)-
• CAS NO: 74852-61-2
• Molecular Formula: C₁₇H₁₉N₃O₃
• Molecular Weight: 313.35
• Product Categories: Piperazine derivates;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles
• Mol File: 74852-61-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 189-190 °C
• Boiling Point: 515.7ºC at 760 mmHg
• Flash Point: 265.7ºC
• Appearance: Brown Solid
• Density: 1.239 g/cm³
• Vapor Pressure: 9.63E-11mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 6.17±0.40(Predicted)
• Water Solubility: 36.9μg/L at 20℃
• CAS DataBase Reference: 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine(74852-61-2)
• EPA Substance Registry System: 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine(74852-61-2)

Safety Data

• Hazardous Substances Data: 74852-61-2(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of angiogenesis inhibitors

Flammability and Explosibility

Notclassified

InChI:InChI=1/C17H19N3O3/c1-23-17-8-6-15(7-9-17)19-12-10-18(11-13-19)14-2-4-16(5-3-14)20(21)22/h2-9H,10-13H2,1H3

Upstream product

• 38869-47-5 4-(p-methoxyphenyl)piperazine dihydrochloride 
• 100-00-5 4-chlorobenzonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 252964-65-1 (2S,4R)-itraconazole 
• 252964-68-4 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 106461-41-0 (-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one 
• 89848-52-2 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isobutyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-48-6 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-5-methyl-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-51-1 2-Butyl-4-[4-(4-{4-[(2R,4S)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-50-0 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-53-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isobutyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-47-5 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-37-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isobutyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-31-7 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-5-methyl-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-49-7 cis-4-<4-<4-<4-<<2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>-1-piperazinyl>phenyl>-2,4-dihydro-2-(1-methylethyl)-3H-1,2,4-triazol-3-one 
• 89848-45-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-ethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-44-2 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-one 

Relevant articles and documents

Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic

Itraconazole (ITZ) is an FDA-approved member of the triazole class of antifungal agents. Two recent drug repurposing screens identified ITZ as a promising anticancer chemotherapeutic that inhibits both the angiogenesis and hedgehog (Hh) signaling pathways. We have synthesized and evaluated first- and second-generation ITZ analogues for their anti-Hh and antiangiogenic activities to probe more fully the structural requirements for these anticancer properties. Our overall results suggest that the triazole functionality is required for ITZ-mediated inhibition of angiogenesis but that it is not essential for inhibition of Hh signaling. The synthesis and evaluation of stereochemically defined des-triazole ITZ analogues also provides key information as to the optimal configuration around the dioxolane ring of the ITZ scaffold. Finally, the results from our studies suggest that two distinct cellular mechanisms of action govern the anticancer properties of the ITZ scaffold.

Mono N-arylation of piperazine(III): Metal-catalyzed N-arylation and its application to the novel preparations of the antifungal posaconazole and its advanced intermediate

A novel application of Pd0-catalyzed arylation to mono N-arylated piperazines, its mechanism, and its application towards the novel syntheses of the key differentially N,N′-diarylated piperazine antifungal intermediate N-(4-hydroxyphenyl)-N′-(4-aminophenyl)piperazine 5 as well as posaconazole 1 are described.

Substituted azolone derivatives

The use for the manufacture of a medicament for treating Helicobacter-related diseases of a compound of formula STR1 a pharmaceutically acceptable acid addition salt or a stereochemically isomeric form thereof, wherein X and Y each independently are CH or N; R1, R2 and R3 each independently are hydrogen or C1-4 alkyl; R4 and R5 each independently are hydrogen, halo, C1-4 alkyl, C1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; Z is C=O or CHOH; and Ar is phenyl optionally substituted with up to three substituents selected from hydroxy, C1-4 alkyl, C1-4 alkyloxy, halo, trifluoromethyl, triC1-4 alkylsilyloxy, nitro, amino and cyano or pyridinyl substituted with hydroxy or C1-4 alkyloxy; and --A-- is a radical of formula STR2