4-CHLOROBENZHYDRAZIDE Chemical Properties

Melting point:

162-165 °C (lit.)

Boiling point:

170.60°C

Density 

1.323

refractive index 

1.5618 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.09±0.10(Predicted)

color 

White to Almost white

BRN 

511154

InChI

InChI=1S/C7H7ClN2O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,9H2,(H,10,11)

InChIKey

PKBGHORNUFQAAW-UHFFFAOYSA-N

SMILES

C(NN)(=O)C1=CC=C(Cl)C=C1

CAS DataBase Reference

536-40-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-CHLOROBENZHYDRAZIDE Usage And Synthesis

Chemical Properties

white to light beige crystals, flakes or

Uses

4-Chlorobenzhydrazide has been used in preparation of:

• rod-shaped mesogenic hydrazide derivatives via Schotten-Baumann reaction with 4-n-alkoxybenzoyl chloride
• 4-methoxybenzaldehyde-4-chlorophenyl-1-carbonyl hydrazone
• 4-hydroxybenzaldehyde-4-chlorophenyl-1-carbonylhydrazone
• 2-nitrobenzaldehyde-4-chlorophenyl-1-carbonylhydrazone
• benzaldehyde-4-chlorophenyl-1-carbonylhydrazone

General Description

Effect of acidic catalyst on the reaction of 4-chlorobenzhydrazide and β-naphthol in water has been investigated.

Synthesis

General procedure for the synthesis of 4-chlorobenzoyl hydrazine from ethyl p-chlorobenzoate: hydrazine was synthesized conventionally using the one-pot method (30-58% yield). 10 mmol of ethyl p-chlorobenzoate was dissolved in 20 mL of ethanol. 2 mL of 3N sulfuric acid was added to the solution and the reaction mixture was refluxed for 6 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was neutralized with solid NaHCO3 and filtered to remove excess NaHCO3. To the neutralized reaction mixture, 1.5 mL (3 mmol) of hydrazine monohydrate was added and refluxing was continued for 3-6 h to ensure complete reaction. The ethanol and unreacted hydrazine were evaporated to 1/3 of the original volume by distillation.The reaction mixture was cooled to room temperature, the product was collected by filtration and recrystallized from methanol to give pure 4-chlorobenzhydrazide crystals (see Supporting Information for specific data).

Purification Methods

Crystallise it from H2O. [Beilstein 9 III 1368.]

References

[1] Medicinal Chemistry Research, 2013, vol. 22, # 6, p. 2755 - 2767
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[3] Patent: CN106008390, 2016, A. Location in patent: Paragraph 0015
[4] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1101 - 1109
[5] Oriental Journal of Chemistry, 2017, vol. 33, # 2, p. 971 - 978

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