| Identification | Back Directory | [Name]
6-Chloro-pyridazine-3-carboxylic acid ethyl ester | [CAS]
75680-92-1 | [Synonyms]
6-chlorodazine-3-ethyl formate
Ethyl 6-chloro-3-pyridazinecarboxylate
Ethyl 6-chloropyridazine-3-carboxylate
ethyl 4-chloropyriMidine-2-carboxylate
6-Chloro-pyridazine-3-carboxylic acid ethyl ester
3-Pyridazinecarboxylic acid, 6-chloro-, ethyl ester
6-Chloro-pyridazine-3-carboxylic acid ethyl ester ISO 9001：2015 REACH | [Molecular Formula]
C7H7ClN2O2 | [MDL Number]
MFCD09908168 | [MOL File]
75680-92-1.mol | [Molecular Weight]
186.6 |
| Chemical Properties | Back Directory | [Melting point ]
147-149 °C | [Boiling point ]
320.1±22.0 °C(Predicted) | [density ]
1.311±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
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