5-(4-Methylpiperazin-1-yl)-2-nitroaniline Chemical Properties

Melting point:

152-155°C

Boiling point:

444.2±45.0 °C(Predicted)

Density 

1.264±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

7.35±0.42(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C11H16N4O2/c1-13-4-6-14(7-5-13)9-2-3-11(15(16)17)10(12)8-9/h2-3,8H,4-7,12H2,1H3

InChIKey

MWLBMGPQZJDFKZ-UHFFFAOYSA-N

SMILES

C1(N)=CC(N2CCN(C)CC2)=CC=C1[N+]([O-])=O

CAS DataBase Reference

23491-48-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29335990

5-(4-Methylpiperazin-1-yl)-2-nitroaniline Usage And Synthesis

Description

5-(4-Methylpiperazin-1-yl)-2-nitroaniline (MPNA) is a nitrogen-containing compound that is widely used in scientific research and laboratory experiments. It is a derivative of piperazine, which is a cyclic compound consisting of two piperazine rings joined by a single nitrogen atom. MPNA is a colorless, odorless solid that is soluble in water and organic solvents, making it an ideal compound for a variety of applications.

Chemical Properties

Solid

Uses

5-(4-Methylpiperazin-1-yl)-2-nitroaniline and its derivatives are used as inhibitors of SIRT6 for the treatment of diabetes.

Synthesis

5-Fluoro-2-nitroaniline (1 g), N-methylpiperazine (0.752 ml) and triethylamine (TEA, 1.86 ml) were mixed in N-methylpyrrolidone (NMP, 1.5 ml). The reaction mixture was placed in a microwave reactor and the reaction was heated at 100°C for 20 hours. After completion of the reaction, it was cooled to room temperature, diluted with deionized water (50 ml), stirred for 20 min and filtered. The resulting yellow solid was washed with deionized water and subsequently dried under high vacuum to give the target product 5-(4-methylpiperazine)-2-nitroaniline (1.45 g). Analyzed by liquid chromatography-mass spectrometry (LC-MS) (condition B): retention time (t R) = 0.47 min; molecular ion peak [M + H]+: 237.19.

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 2, p. 278 - 292
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 14, p. 6690 - 6708
[3] Patent: US2004/122237, 2004, A1. Location in patent: Page 247-248
[4] Patent: WO2004/18419, 2004, A2. Location in patent: Page 260
[5] Patent: US2010/81653, 2010, A1. Location in patent: Page/Page column 12

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