6-Chloro-4-methylpyridazin-3-amine Chemical Properties

Melting point:

137 °C

Boiling point:

360.2±37.0 °C(Predicted)

Density 

1.349±0.06 g/cm3(Predicted)

storage temp. 

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

pka

4.49±0.10(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C5H6ClN3/c1-3-2-4(6)8-9-5(3)7/h2H,1H3,(H2,7,9)

InChIKey

HSAHCMOZFNSMLH-UHFFFAOYSA-N

SMILES

C1(N)=NN=C(Cl)C=C1C

Safety Information

HS Code 

2933998090

6-Chloro-4-methylpyridazin-3-amine Usage And Synthesis

Uses

6-Chloro-4-methylpyridazin-3-amine is a reagent used in organic synthesis transformations.

Synthesis

General procedure for the synthesis of 3-amino-5-methyl-6-chloropyridazine and 3-amino-4-methyl-6-chloropyridazine from 3,6-dichloro-4-methylpyridazine: [Linholter, S., et al., Acta Chem. Scand. 15:1660-1666 (1961)]. To a solution of 3,6-dichloro-4-methylpyridazine (200 mg) in ethanol (3 mL) was added liquid ammonia (3 mL). The reaction mixture was placed in a sealed tube and heated at 120 °C for 12 hours. After completion of the reaction, it was cooled to room temperature and the methanol and ammonia were removed by evaporation. The residue was purified by fast chromatography (eluent: ethyl acetate) to give 153 mg of a mixture of 3-amino-5-methyl-6-chloropyridazine and 3-amino-4-methyl-6-chloropyridazine (1:1 ratio) in 87% yield. The mixture was used directly in the subsequent reaction without further separation.

References

[1] Patent: WO2007/33080, 2007, A2. Location in patent: Page/Page column 26; 37
[2] Patent: WO2014/72261, 2014, A1. Location in patent: Page/Page column 48
[3] Pharmaceutical Bulletin, 1957, vol. 5, p. 229,233
[4] Australian Journal of Chemistry, 1986, vol. 39, # 11, p. 1803 - 1809
[5] Pharmaceutical Bulletin, 1957, vol. 5, p. 229,233

6-Chloro-4-methylpyridazin-3-amine(64068-00-4)Related Product Information

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