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Home > Encyclopedia > 3,6-dichloropyridazin-4-amine

3,6-dichloropyridazin-4-amine

3,6-dichloropyridazin-4-amine structure

3,6-dichloropyridazin-4-amine 

structure
  • CAS No:

    823-58-5

  • Formula:

    C4H3Cl2N3

  • Chemical Name:

    3,6-dichloropyridazin-4-amine

  • Synonyms:

    NSC 170664;3,6-Dichloro-4-Pyridazinamine;4-Amino-3,6-dihydropyridazine;3,6-dichloropyridazin-4-amine;4-AMino-3,6-dicholropyridazine;4-AMino-3,6-dichloropyridazine;3,6-Dichloro-4-aMinopyridazine;4-PyridazinaMine, 3,6-dichloro-;3,6-Dichloropyridazin-4-amine, 4-Amino-3,6-dichloro-1,2-diazine

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

3,6-dichloropyridazin-4-amine Basic Attributes

163.99

162.97000

170664

DTXSID40305400

2933990090

Characteristics

51.8

1.1

1.606g/cm3

203 °C

173.3ºC

1.633

Safety Information

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3,6-dichloropyridazin-4-amine Use and Manufacturing

3, 6-dichloropyridazin-4-amine A MW vial was charged with 3, 4, 6-trichloropyridazine (5 g, 27.3 mmol) and 7N NHA MW vial was charged with 3, 4, 6-trichloropyridazine (5 g, 27.3 mmol) and 7N NH3 in MeOH (19.47 mL, 136 mmol). The MW vial was sealed and the resulting mixture was submitted to MWirradiation at 100 00 for 30 mm. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 35-60percent) to afford the title product (1.49 g, 8.63 mmol, 32percent yield) as yellow solid. tR: 1.61 mm (HPLC 1); tR: 0.45 mm (LC-MS 2); ESI-MS: 163 [M+H] (LC-MS 2); R = 0.40 (hexane/EtOAc 1:1).4-Bromo-3, 6-dichloro-pyridazine (15.0 g, 65.8 mmol, prepared as described in WO 20081 16815) was dissolved in EtOH (73.1 mL) and introduced into an autoclave. At rt, gaseous NH3 (4.48 g, 263mmol) was introduced, and the reaction mixture was then stirred over night at reflux. The solution was concentrated in vacuo and the residue was triturated with EtOAc, the insoluble part was filtrated off, and the mother liquor evaporated to give the crude product. This was purified by Flash-Chromatography, eluting with cyclohexan /EtOAc 1/1 +2.5percent Et3N, to give the title compound as a pale brown solid (5.82g, 53percent). LCMS (method ZCQ13): Rt. 0.3min, 164/166/168 (M+H)

Computed Properties

Molecular Weight:163.99
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:162.9704025
Monoisotopic Mass:162.9704025
Topological Polar Surface Area:51.8
Heavy Atom Count:9
Complexity:99.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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