67914-60-7

Basic information

• Product Name: 4-(1-Acetylpiperazin-4-yl)phenol
• Synonyms: TIMTEC-BB SBB003353;N-ACETYL-4-HYDROXYPHENYL PIPERAZINE;N-ACETYL-4-(4-HYDROXYPHENYL)PIPERAZINE;Branchedchainofketoconazole;4-(1-Acetylpiperazin-4-yl)phenol;4-(4-ACETYL-1-PIPERAZINYL)PHENOL;AHPP;1-ACETYL-P-HYDROXYPHENYL PIPERAZINE
• CAS NO: 67914-60-7
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• EINECS: 267-744-8
• Product Categories: Chemical intermediate for Ketoconazole;Piperidines, Piperidones, Piperazines;Piperaizine;Miscellaneous;Chemical Amines;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks;Piperazines
• Mol File: 67914-60-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 180-185 °C(lit.)
• Boiling Point: 361.21°C (rough estimate)
• Flash Point: 229.9 °C
• Appearance: White to slightly pink or beige/Powder
• Density: 1.1115 (rough estimate)
• Vapor Pressure: 5.91E-09mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.18±0.30(Predicted)
• Water Solubility: 4.3 g/L (20 ºC)
• BRN: 795777
• CAS DataBase Reference: 4-(1-Acetylpiperazin-4-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-Acetylpiperazin-4-yl)phenol(67914-60-7)
• EPA Substance Registry System: 4-(1-Acetylpiperazin-4-yl)phenol(67914-60-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• Hazardous Substances Data: 67914-60-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

1-Acetyl-4-(4-hydroxyphenyl)piperazine may be used in the preparation of 1-acetyl-4-(4-octadecyloxyphenyl)piperazine. It may also be used in the multi-step synthesis of ketoconazole, its 1,2,4-triazole and thiazole analogs.

General Description

1-Acetyl-4-(4-hydroxyphenyl)piperazine (AHPP), a piperazine derivative, is a structural analog of acetaminophen. Its multi-step preparation using bis-(2-chloroethyl)amine hydrochloride and p-aminophenol as starting materials has been reported.2

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H16N2O2/c1-10(15)13-6-8-14(9-7-13)11-2-4-12(16)5-3-11/h2-5,16H,6-9H2,1H3

Upstream product

• 123-30-8 4-amino-phenol 
• 56621-48-8 1-(4-hydroxyphenyl)piperazine 
• 108-24-7 acetic anhydride 
• 123-91-1 1,4-dioxane 
• 38869-37-3 1-(4-hydroxy-phenyl)-piperazine dihydrobromide 
• 1336-21-6 ammonium hydroxide 
• 1972-28-7 diethylazodicarboxylate 
• 38869-47-5 4-(p-methoxyphenyl)piperazine dihydrochloride 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 133345-21-8 1-(4-Acetoxyphenyl)-4-acetylpiperazine 

Downstream Products

• 65277-42-1 ketoconazole 
• 65277-42-1 trans-Ketoconazole 
• 142128-66-3 (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane 
• 142128-67-4 (2R,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane 
• 145782-08-7 trans-1-acetyl-4-<-<<2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>piperazine 
• 145782-08-7 cis-1-acetyl-4-<-<<2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>piperazine 
• 67915-35-9 cis-1-acetyl-4-<4-<<2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl>-methoxy>phenyl>piperazine 
• 94133-71-8 (+/-)-1-acetyl-4-<4-(2,3-dihydroxypropoxy)phenyl>piperazine 
• 1025711-74-3 4-(4-isopropylpiperazin-1-yl)phenyl 3-(1-tert-butyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)azetidine-1-carboxylate 
• 515160-72-2 1-(4-(2-methoxyethoxy)phenyl)piperazine 

Relevant articles and documents

Design and synthesis of the novel, selective WZ4002 analogue as EGFR-L858R/T790M tyrosine kinase inhibitors for targeted drug therapy in non-small-cell lung cancer (NSCLC)

To conquer the drug-resistance of first-generation EGFR (epidermal growth factor receptor) kinase inhibitors and second-generation inhibitors’ non-selective toxicities in Non-Small Cell Lung Cancer (NSCLC) patients, a series of WZ4002 derivatives (6–46) were discovered as novel double mutant EGFR-L858R/T790M TK inhibitors. This objective was attained by employing structure-based drug design and traditional optimization strategies based on the WZ4002 scaffold. Among the synthesized compounds, representative compounds 8 and 38 displayed significant anti-proliferative activity on the Gefitinib-resistant cell line NCI-H1975, with an IC50 value of 0.179 μM and 0.173 μM, respectively. Also, these compounds exhibited moderate anti-proliferative activity against the A549 cell, with an IC50 of 0.550 μM and 0.528 μM respectively, suggesting their improved selectivity over the mutant EGFR-L858R/T790M. Excitingly, both these compounds showed significant inhibition of the double mutant EGFR-L858R/T790M TK with an IC50 value of 0.0063 μM and 0.0060 μM, respectively. The IC50 values of both the promising compounds against the HepG2 cell line were more than 1 μM, indicating safety for normal cells. Covalent docking and MD simulation further confirm their irreversible binding mode with the target protein. These results demonstrate that compounds 8 and 38 would be promising lead compound-targeting double mutant EGFR-L858R/T790M TK.

NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE and INFLAMMATORY DISEASES

The present invention relates to compounds of formula (I) that are inhibitors of PDElA, a phosphodiesterase that is involved in the modulation of the degradation of cartilage, joint degeneration and diseases involving such degradation and/or inflammation.

Antifungal azole derivatives having a fluorinated vinyl group and process for preparing same

An antifungal compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein: X is CH or N; Y is O, R1and R2are each independently F or Cl; R3is a thiophenyl, naphthyl, or phenyl group, the phenyl group being optionally substituted with one or more substituents selected from the group consisting of C1-4alkyl, C1-4haloalkyl, C1-4alkoxy, methylenedioxy and halogen; and R4is H or trifluoromethyl.