| Identification | More | [Name]
4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol | [CAS]
112559-81-6 | [Synonyms]
1-(4-HYDROXYPHENYL)-4-(4-NITROPHENYL)-PIPERAZINE | [EINECS(EC#)]
601-189-8 | [Molecular Formula]
C16H17N3O3 | [MDL Number]
MFCD08460988 | [Molecular Weight]
299.32 | [MOL File]
112559-81-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
>90°C (dec.) | [Boiling point ]
540.8±50.0 °C(Predicted) | [density ]
1.317±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly, Heated) | [form ]
Solid | [pka]
12.18±0.30(Predicted) | [color ]
Yellow to Brown | [InChI]
InChI=1S/C16H17N3O3/c20-16-7-5-14(6-8-16)18-11-9-17(10-12-18)13-1-3-15(4-2-13)19(21)22/h1-8,20H,9-12H2 | [InChIKey]
BNHYDULILNJFFY-UHFFFAOYSA-N | [SMILES]
C1(O)=CC=C(N2CCN(C3=CC=C([N+]([O-])=O)C=C3)CC2)C=C1 | [CAS DataBase Reference]
112559-81-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
4-[4-(4-Nitrophenyl)-1-piperazinyl]phenol is a key intermediate in the synthesis of triazole medicines, such as itraconazole (I937500), which are used in curing deep department fungal infections. Inhibitor of endothelial cell proliferation. | [Uses]
4-[4-(4-Nitrophenyl)-1-piperazinyl]phenol is a key intermediate in the synthesis of triazole medicines, used in curing deep department fungal infections. Inhibitor of endothelial cell proliferation. | [Synthesis]
Under nitrogen protection, 420 g (2.36 mol) of 4-(1-piperazinyl)phenol, 520.6 g (3.30 mol) of 4-chloronitrobenzene, and 457.5 g (3.54 mol) of N,N-diisopropylethylamine (Huenig's base) were suspended in 1260 mL of N-methylpyrrolidone. The mixture was heated to 120-125°C until a clarified solution was formed. This temperature was maintained and the progress of the reaction was monitored by HPLC. Upon completion of the reaction (5-7 hr), the reaction solution was cooled to 75-80°C. 6.3 L of isopropanol was slowly added to the reaction mixture over a period of about 30 min while maintaining the temperature at 75-80°C (with slight heating if necessary). At the end of the addition, the product began to precipitate as yellow crystals. The suspension was cooled to 20-25°C and stirred at this temperature overnight. Subsequently, the suspension is further cooled to -10 to -5°C and stirred for 30 minutes. The product was collected by filtration and washed sequentially with 1.7 L of isopropanol and 5 x 840 mL of warm water (35-40°C). Finally, the product was dried under vacuum at 50°C (accompanied by a slight stream of nitrogen) to constant weight. The yield was 96% and the purity as determined by HPLC was 93%, which corresponded to the standard. | [References]
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3635 - 3649
[2] Patent: EP1230231, 2005, B1. Location in patent: Page/Page column 4
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7363 - 7374
[4] Patent: WO2018/45106, 2018, A1. Location in patent: Paragraph 00131
[5] Patent: WO2018/45104, 2018, A1. Location in patent: Paragraph 00156 |
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