4-Chlorophenylhydrazine hydrochloride Chemical Properties

Melting point:

216 °C (dec.)(lit.)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

color 

White to pink

Water Solubility 

Soluble in hot water, methanol.

BRN 

3596254

InChI

InChI=1S/C6H7ClN2.ClH/c7-5-1-3-6(9-8)4-2-5;/h1-4,9H,8H2;1H

InChIKey

YQVZREHUWCCHHX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1073-70-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37-36-26

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29280090

MSDS

• Language:English Provider:1-(4-chlorophenyl)hydrazine hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-Chlorophenylhydrazine hydrochloride Usage And Synthesis

Chemical Properties

white to pink crystalline powder

Uses

4-Chlorophenylhydrazine hydrochloride is used as a pharmaceutical intermediates.

General Description

4-Chlorophenylhydrazine hydrochloride reacts with 3-acetonyl-5-cyano-1,2,4-thiadiazole to yield 5-cyano-3-(5-chloro-2-methylindol-3-yl)-1,2,4-thiadiazole and 5-cyano-3-[1-(4-chlorophenyl)-3,5-dimethylpyrazol-4-yl]-1,2,4-thiadiazole.

Synthesis

The general procedure for the synthesis of p-chlorophenylhydrazine hydrochloride from 4-bromochlorobenzene is as follows: 98.25 g of 4-bromochlorobenzene and 3.3 equivalents of 71% hydrazine hydrate were added to a reaction vessel, to which were added 10 wt.% of the phase transfer catalyst PEG400, 3 times the weight of the solvent acrylhydrazine, and 20 wt.% of a catalyst (copper sulfate in the ratio of copper sulfate to cobalt chloride by mass of 3:1). The reaction process consisted of slowly increasing the temperature to 152 °C, refluxing or packing pressure reaction at atmospheric pressure, and maintaining the reaction at this temperature for 10 hours. During this time, the reaction process was monitored by HPLC and stopped when the amount of p-chlorophenylhydrazone no longer increased. After completion of the reaction, the solid was separated by filtration and the filtrate was distilled to remove the solvent. To the obtained residue, 30% hydrochloric acid was added, the pH was adjusted to 3, and the residue was filtered with thorough stirring. The filtrate was washed with water and dried at 55°C to finally obtain p-chlorophenylhydrazine hydrochloride. In this embodiment, the yield of p-chlorophenylhydrazine hydrochloride was 88.1% and the HPLC purity was 99.29%.

References

[1] Patent: CN105968048, 2016, A. Location in patent: Paragraph 0030-0054; 0055-0059; 0060-0069
[2] Patent: CN106045876, 2016, A. Location in patent: Paragraph 0055; 0056; 0057; 0058; 0059
[3] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
[4] Tetrahedron, 2014, vol. 70, # 26, p. 4043 - 4048

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