6-Chloro-pyridazine-3-carboxylic acid ethyl ester Chemical Properties

Melting point:

147-149 °C

Boiling point:

320.1±22.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

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

form 

Crystalline Powder

pka

-0.94±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C7H7ClN2O2/c1-2-12-7(11)5-3-4-6(8)10-9-5/h3-4H,2H2,1H3

InChIKey

GVSVPKDEHFOXSW-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

29339980

6-Chloro-pyridazine-3-carboxylic acid ethyl ester Usage And Synthesis

Uses

Ethyl 6-Chloropyridazine-3-carboxylate is a useful research chemical compound used in the preparation of hetero-substituted pyridazine derivatives using alkylation of chloropyridazinecarboxylate followed by cross-coupling and heterocyclization.

Synthesis

Ethyl 3-pyridazinone-6-carboxylate (1.17 g, 6.96 mmol) was used as a raw material, which was dissolved in phosphoryl chloride (12 mL) and the reaction was heated at 100 °C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to about 3 mL. The concentrated residue was slowly poured into ice water and slowly neutralized with 10% aqueous sodium hydroxide solution under ice bath conditions. The neutralized mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and subsequently dried with anhydrous magnesium sulfate. The dried organic phase was evaporated under reduced pressure to give the crude product. The crude product was purified by rapid chromatography on silica gel (200-300 mesh, eluent ratio hexane: ethyl acetate = 3:1) to afford ethyl 6-chloropyridazine 3-carboxylate (892 mg, yield 68.7%) as a white solid. The melting point was measured to be 145.6-146.7 °C (literature values 154-155 °C [56]).

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 598 - 611
[2] Patent: CN106187910, 2016, A. Location in patent: Paragraph 0242; 0243
[3] Nippon Kagaku Zasshi, 1957, vol. 78, p. 577,579, 580
[4] Chem.Abstr., 1959, p. 5275
[5] Bulletin de la Societe Chimique de France, 1959, p. 1793,1796

6-Chloro-pyridazine-3-carboxylic acid ethyl ester(75680-92-1)Related Product Information

• 3-Pyridazinesulfonyl chloride, 6-chloro-
• 3-Pyridazinecarboxylic acid, 6-chloro-,1-methylethyl ester
• 6-Chloropyrazine-2-carboxylic acid
• 6-Chlorooxazolo[4,5-b]pyridin-2(3H)-one
• 6-chlorophthalazine
• 2-Pyrazinecarboxylic acid, 6-chloro-, ethyl ester
• 6-chloropyrido[2,3-d]pyrimidin-2-amine
• Pyridazin-3-ylmethanol
• 3-Pyridazineacetic acid
• 6-Oxo-1,6-dihydro-pyridazine-3-carboxylicacid
• 6-Chloropyridazine-3-carboxamide
• 3-Pyridazinecarboxylic acid
• 6-AMINO-PYRIDAZINE-3-CARBOXYLIC ACID
• 6-Chloropyridazine-3-carboxylic acid
• METHYL 6-CHLOROPYRIDAZINE-3-CARBOXYLATE
• 3,4-Pyridazinediamine, 6-chloro-
• 3-Pyridazinecarboxaldehyde, 6-chloro- (9CI)
• Pyridazine-3-carboxylic acid ethyl ester