4-TERT-BUTYL-3,6-DICHLOROPYRIDAZINE Chemical Properties

Melting point:

37-40 °C

Boiling point:

297.3±35.0 °C(Predicted)

Density 

1.231

refractive index 

1.52

storage temp. 

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

solubility 

Chloroform, Dichloromethane

form 

Oil

pka

-0.40±0.10(Predicted)

color 

Colourless

EPA Substance Registry System

Pyridazine, 3,6-dichloro-4-(1,1-dimethylethyl)- (22808-29-3)

Safety Information

Toxicity

rat,LDLo,oral,500mg/kg (500mg/kg),SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYEBEHAVIORAL: COMABEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,National Technical Information Service. Vol. OTS0544009,

4-TERT-BUTYL-3,6-DICHLOROPYRIDAZINE Usage And Synthesis

Chemical Properties

Colourless Oil

Synthesis

Synthesis of compound J.1. To a 250 mL round bottom flask was added 3,6-dichloropyridazine (1.49 g, 10 mmol, 1.0 eq.), silver nitrate (0.17 g, 1 mmol, 0.1 eq.), deionized water (30 mL), pivalic acid (3.57 g, 35 mmol, 3.5 eq.), and concentrated sulfuric acid (1.6 mL, 30 mmol, 3.0 eq.). The reaction mixture was heated to 70 °C and kept at a constant temperature. An aqueous solution (10 mL) of ammonium persulfate (2.28 g, 10 mmol, 1.0 eq.) was added slowly and dropwise over 10 minutes. After the dropwise addition, the reaction was continued with stirring at 70 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature. The reaction mixture was slowly poured into ice water (100 mL) and the pH was adjusted with aqueous ammonium hydroxide to 8. The aqueous phase was extracted with dichloromethane (3 × 250 mL). The organic phases were combined, filtered through a cotton plug, washed with 1N aqueous NaOH (70 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification of the crude product by fast column chromatography (20% ethyl acetate/hexane) afforded 4-tert-butyl-3,6-dichloropyridazine (1.32 g, 64% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ: 7.5 (s, 1H), 1.5 (s, 9H); Rf = 0.5 (80% ethyl acetate/hexane).

References

[1] Patent: US2009/5359, 2009, A1. Location in patent: Page/Page column 39
[2] Patent: US2009/36419, 2009, A1. Location in patent: Page/Page column 84
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7089 - 7092
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 20, p. 6030 - 6033

4-TERT-BUTYL-3,6-DICHLOROPYRIDAZINE(22808-29-3)Related Product Information

• 3,6-Dichloropyridazine