4-Nitrophenylhydrazine hydrochloride Chemical Properties

Melting point:

205-207°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO, Methanol, Water

form 

Solid

color 

Brown to Reddish Brown

BRN 

3569014

InChI

InChI=1S/C6H7N3O2.ClH/c7-8-5-1-3-6(4-2-5)9(10)11;/h1-4,8H,7H2;1H

InChIKey

ZWWXDCOPVYATOQ-UHFFFAOYSA-N

SMILES

N(C1=CC=C([N+]([O-])=O)C=C1)N.[H]Cl

CAS DataBase Reference

636-99-7(CAS DataBase Reference)

EPA Substance Registry System

4-Nitrophenylhydrazine hydrochloride (636-99-7)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-24/25-22

RIDADR 

2811

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

2928009090

MSDS

• Language:English Provider:4-Nitrophenylhydrazine hydrochloride
• Language:English Provider:ALFA

4-Nitrophenylhydrazine hydrochloride Usage And Synthesis

Chemical Properties

PINK TO ORANGE CRYSTALLINE POWDER

Uses

4-Nitrophenylhydrazine is a nitro substituted aryl hydrazine with potential anticancer activity.

Synthesis

The general procedure for the synthesis of 4-nitrophenylhydrazine hydrochloride from 4-nitroaniline was as follows: 4-nitroaniline (1.47 g, 10.6 mmol) was dissolved in concentrated hydrochloric acid (2 mL) and the solution was cooled to 0°C. A solution of sodium nitrite (717 mg, 10.4 mmol) dissolved in water (4 mL) was added dropwise to the above reaction mixture under ice bath conditions with continuous stirring for 1 hour. Subsequently, a pre-cooled solution of concentrated hydrochloric acid (2 mL) of stannous chloride (4.7 g, 20.8 mmol) was slowly added to the diazo reaction mixture. The reaction mixture was continued to be stirred at 0°C for 2 hours. Upon completion of the reaction, the resulting yellow-orange precipitate was collected and washed thoroughly with ice-cold water until the filtrate was neutral (pH ≈ 7). Finally, the precipitate was dried under vacuum conditions overnight to afford the target product 4-nitrophenylhydrazine hydrochloride (640 mg, 4.18 mmol, 39% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 4.49 (s, 2H), 6.78 (d, J=8.78 Hz, 2H), 7.98 (d, J=9.29 Hz, 2H), 8.41 (s, 1H).

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2739 - 2752
[2] Russian Chemical Bulletin, 2005, vol. 54, # 10, p. 2417 - 2424
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4692 - 4696
[4] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 2, p. 381 - 390
[5] Oriental Journal of Chemistry, 2017, vol. 33, # 2, p. 1041 - 1044

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