1,4-Dichlorophthalazine Chemical Properties

Melting point:

160-162 °C (lit.)

Boiling point:

397.3±22.0 °C(Predicted)

Density 

1.486±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Chloroform, Methanol

pka

-0.44±0.30(Predicted)

form 

Powder or Crystalline Powder

color 

White to yellow

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C8H4Cl2N2/c9-7-5-3-1-2-4-6(5)8(10)12-11-7/h1-4H

InChIKey

ODCNAEMHGMYADO-UHFFFAOYSA-N

SMILES

C1(Cl)C2=C(C=CC=C2)C(Cl)=NN=1

CAS DataBase Reference

4752-10-7(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1,4-Dichlorophthalazine Usage And Synthesis

Uses

1,4-Dichlorophthalazine was used as starting reagent in the synthesis of series of 4-aryl-1-(4-methylpiperazin-1-yl)phthalazines. It was used as coupling reagent in the synthesis of novel soluble polymer-bound ligand. It was often used as building block in medicinal chemistry synthesis.

Uses

1,4-Dichlorophthalazine Oftens used building block in medicinal chemistry synthesis.1,2

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 2708, 1965 DOI: 10.1139/v65-379

Synthesis

General procedure for the synthesis of 1,4-dichlorophthalazine from phthaloyl hydrazine: phthaloyl hydrazine (1.68 g, 10 mmol) was added to a stirred solution of phosphoryl chloride (15 ml). The mixture was heated to 110°C and kept for 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature. The mixture was slowly added dropwise to crushed ice and stirred for 10 minutes. Subsequently, the mixture was filtered through a Brinell funnel. The filter cake was washed to neutrality with distilled water and dried in vacuum. 1,4-Dichlorophthalazine (1.85 g, 90.1% yield) was finally obtained as a white solid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1236 - 1238
[2] European Journal of Medicinal Chemistry, 2014, vol. 85, p. 235 - 244
[3] Chemical Biology and Drug Design, 2013, vol. 81, # 5, p. 591 - 599
[4] New Journal of Chemistry, 2016, vol. 40, # 7, p. 6070 - 6076
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 6, p. 1576 - 1579

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