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Sigma-Aldrich

1-Acetyl-4-(4-hydroxyphenyl)piperazine

98%

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O2
CAS Number:
67914-60-7
Molecular Weight:
220.27
EC Number:
267-744-8
MDL number:
MFCD00044905
UNSPSC Code:
12352100
PubChem Substance ID:
24873593

Assay

98%

mp

180-185 °C (lit.)

SMILES string

CC(=O)N1CCN(CC1)c2ccc(O)cc2

InChI

1S/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

InChI key

AGVNLFCRZULMKK-UHFFFAOYSA-N

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

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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New process for synthesis of 1-acetyl-4-(4-hydroxyphenyl) piperazine [J].
Zheng, CZ, et al.
Huaxue Shiji, 10, 27-27 (2010)
Synthesis of Ketoconazole by Phase-transfer Catalysis [J].
Chen YH and Long SJ.
Chinese Journal of Pharmaceuticals / Chung-kuo i yao kung yeh tsa chih, 8, 005-005 (2008)
Synthesis of 1, 2,4-triazole and thiazole analogs of ketoconazole.
Huang LF, et al.
Journal of Heterocyclic Chemistry, 34(2), 469-476 (1997)
Design of new potent and selective secretory phospholipase A2 inhibitors. 6-Synthesis, structure-activity relationships and molecular modelling of 1-substituted-4-[4,5-dihydro-1,2,4-(4H)-oxadiazol-5-one-3-yl(methyl)]-functionalized aryl piperazin/one/dione derivatives.
Meddad-Belhabich N, et al.
Bioorganic & Medicinal Chemistry, 18(10), 3588-3600 (2010)
S Shi et al.
Biosensors & bioelectronics, 72, 205-210 (2015-05-20)
We propose in this work a general and versatile methodology for electrochemical monitoring of persistent pharmaceutical micropollutants. The system presented is based on an electroactive and electropolymerized hapten (mimetic molecule of the pollutant to be detected) and a specific antibody

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