1-(4-Nitrophenyl)piperazine Chemical Properties

Melting point:

131-133 °C (lit.)

Boiling point:

346.25°C (rough estimate)

Density 

1.1933 (rough estimate)

refractive index 

1.4830 (estimate)

storage temp. 

Storage temp. 2-8°C

form 

Crystalline Powder, Crystals and/or Chunks

pka

8.68±0.10(Predicted)

color 

White to beige to gray

InChI

InChI=1S/C10H13N3O2/c14-13(15)10-3-1-9(2-4-10)12-7-5-11-6-8-12/h1-4,11H,5-8H2

InChIKey

VWOJSRICSKDKAW-UHFFFAOYSA-N

SMILES

N1(C2=CC=C([N+]([O-])=O)C=C2)CCNCC1

CAS DataBase Reference

6269-89-2(CAS DataBase Reference)

NIST Chemistry Reference

N-p-nitrophenylpiperazine(6269-89-2)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-24/25-36

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:1-(4-Nitrophenyl)piperazine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-(4-Nitrophenyl)piperazine Usage And Synthesis

Chemical Properties

yellow to ochre powder

Uses

1-(4-Nitrophenyl)piperazine is a useful synthetic intermediate in the synthesis of Itraconazole (I937500); an orally active antimycotic structurally related to Ketoconazole. Also antifungal.

General Description

Inclusion interactions of 1-(4-nitrophenyl)piperazine with 4-sulfonatocalix[n]arenes were investigated by UV spectroscopy and fluorescence spectroscopy.

Synthesis

A solution of 1-chloro-4-nitrobenzene (650 g, 4.140 mol) in diethylene glycol dimethyl ether (1 L) was slowly added dropwise to a solution of piperazine (2.84 Kg, 33.12 mol) in diethylene glycol dimethyl ether (500 mL) at 100 °C. The reaction mixture was stirred continuously at 100°C for 6 hours. Upon completion of the reaction, the mixture was cooled to 40-45 °C and water (5 L) was slowly added to quench the reaction. Subsequently, the mixture was warmed to room temperature and stirring was continued for 1 hour. The precipitated solid was collected by filtration, washed sequentially with water (1 L) and petroleum ether (500 mL), and dried to give 700 g (81% yield) of 4-nitrophenylpiperazine as a yellow solid. [TLC detection conditions: ethyl acetate:petroleum ether (3:7); Rf value: 0.70].

References

[1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[2] Organic Letters, 2016, vol. 18, # 20, p. 5272 - 5275
[3] Patent: WO2016/79536, 2016, A1. Location in patent: Page/Page column 34-35
[4] Patent: WO2017/203270, 2017, A1. Location in patent: Page/Page column 30; 33; 34
[5] Patent: WO2018/45106, 2018, A1. Location in patent: Paragraph 00133

1-(4-Nitrophenyl)piperazine(6269-89-2)Related Product Information

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