1,4-DICHLOROPYRIDO[4,3-D]PYRIDAZINE Chemical Properties

Melting point:

159 °C

Boiling point:

440.8±40.0 °C(Predicted)

Density 

1.573±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

1.19±0.30(Predicted)

color 

Pale yellow

InChI

InChI=1S/C7H3Cl2N3/c8-6-4-1-2-10-3-5(4)7(9)12-11-6/h1-3H

InChIKey

LMVNXZZDBBSCSG-UHFFFAOYSA-N

SMILES

C1(Cl)=NN=C(Cl)C2=CC=NC=C12

Safety Information

HS Code 

2933998090

1,4-DICHLOROPYRIDO[4,3-D]PYRIDAZINE Usage And Synthesis

Uses

1,4-Dichloropyrido[4,3-d]pyridazine is a useful research chemical.

Synthesis

General procedure for the synthesis of 1,4-dichloropyrido[4,3-D]pyridazine from 1,4-dihydroxypyrido[4,3-D]pyridazine: pyrido[3,4-d]pyridazine-1,4-diol (1.83 g, 11.2 mmol) and phosphorus trichloride (8.4 mL, 89.7 mmol) were added to a round bottomed flask. N,N-diisopropylethylamine (DIPEA, 2.0 mL, 11.2 mmol) was slowly added to the reaction system. The resulting suspension was heated and refluxed at 100 °C for 1 h. The reaction solution was gradually transformed into a brown solution. Upon completion of the reaction, the excess phosphorus trichloride was removed by rotary evaporator. The residue was dissolved in dichloromethane (DCM) and added slowly and dropwise to a mixed system of ice-water mixture and saturated aqueous sodium bicarbonate (NaHCO3). The saturated NaHCO3 solution was continued to be added dropwise until the aqueous phase was neutral. The organic and aqueous phases were separated and the aqueous phase was further extracted with dichloromethane (500 mL). The organic phases were combined, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the target product 1,4-dichloropyrido[3,4-d]pyridazine (1.74 g, 8.7 mmol, 78% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 9.78 (d, J = 0.9 Hz, 1H), 9.27 (d, J = 5.7 Hz, 1H), 8.09 (dd, J = 5.7 Hz, 0.9 Hz, 1H). Mass spectrometry analysis (Method 2): retention time (RT) 1.16 min, electrospray positive ionization mode (ES+) m/z 209.0 [M + H]+.

References

[1] Patent: WO2015/1348, 2015, A1. Location in patent: Paragraph 00183
[2] Patent: WO2014/191737, 2014, A1. Location in patent: Paragraph 00234
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4607 - 4610
[4] Patent: WO2009/35568, 2009, A1. Location in patent: Page/Page column 41
[5] Patent: WO2009/35568, 2009, A1. Location in patent: Page/Page column 40-41

1,4-DICHLOROPYRIDO[4,3-D]PYRIDAZINE(14490-19-8)Related Product Information

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