4-Cyanophenylhydrazine hydrochloride Chemical Properties

Melting point:

241-244 °C (dec.)(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

Powder

color 

Pale orange to brown

Sensitive 

Moisture Sensitive

BRN 

3565486

InChI

InChI=1S/C7H7N3.ClH/c8-5-6-1-3-7(10-9)4-2-6;/h1-4,10H,9H2;1H

InChIKey

UXDLLFIRCVPPQP-UHFFFAOYSA-N

SMILES

C1(C#N)=CC=C(NN)C=C1.Cl

CAS DataBase Reference

2863-98-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Harmful

PackingGroup 

III

HS Code 

29280000

MSDS

• Language:English Provider:4-Cyanophenylhydrazine hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Cyanophenylhydrazine hydrochloride Usage And Synthesis

Chemical Properties

Pale orange to brown powder

Uses

4-Cyanophenylhydrazine Hydrochloride (cas# 2863-98-1) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 4-cyanophenylhydrazine hydrochloride from 4-aminobenzonitrile was as follows: to a stirring suspension of 4-aminobenzonitrile (50 g, 423 mmol) concentrated hydrochloric acid (550 mL) was slowly added dropwise an aqueous sodium nitrite solution (31.5 g, 457 mmol, dissolved in 200 mL of water) at a low temperature of -5 to 0 °C. Keeping the reaction temperature below 0 °C, a solution of tin(II) chloride dihydrate (477 g, 2.1 mol) concentrated hydrochloric acid (370 mL) pre-cooled to 0 °C was added to the above diazotized solution. The reaction mixture was continued to be stirred for 15 minutes. Upon completion of the reaction, the resulting white precipitate was collected by filtration, washed with diethyl ether and recrystallized from aqueous ethanol. The resulting 4-cyanophenylhydrazine hydrochloride had a melting point of 234-236 °C (literature value 235-237 °C) and yielded 60 g in 84% yield.

References

[1] Journal of the American Chemical Society, 2016, vol. 138, # 30, p. 9377 - 9380
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4581 - 4590
[3] Synthetic Communications, 2014, vol. 44, # 24, p. 3563 - 3571
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 19, p. 3023 - 3032
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429

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