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Chemical Structure| 570416-05-6

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Product Details of [ 570416-05-6 ]

CAS No. :570416-05-6
Formula : C9H10ClN3
M.W : 195.65
SMILES Code : CCCC1=NN2C(C=C1)=NC(Cl)=C2

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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 570416-05-6 ]

[ 570416-05-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 112581-77-8 ]
  • [ 927-77-5 ]
  • [ 570416-05-6 ]
YieldReaction ConditionsOperation in experiment
99% 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; toluene; at 20 - 30℃;Product distribution / selectivity; Reference Example 2 Into a 500 mL reaction container purged with nitrogen, 20.4 g of <strong>[112581-77-8]2,6-dichloroimidazo[1,2-b]pyridazine</strong> (content: 92% by weight), 150mL of toluene and 0.27 g of 1,3-bis(diphenylphosphino)propanenickel chloride (II) (content: 94% by weight) were charged, and 50 mL of a tetrahydrofuran solution of n-propylmagnesium bromide (concentration: 2 mole/L) was added dropwise thereto at 20 to 30C to effect reaction. After completion of the reaction, the reaction mixture was added dropwise into 75 g of 10% by weight aqueous sulfuric acid solution. The resultant mixture was stirred and left, and the organic layer was separated. The organic layer was washed with 10% by weight aqueous sulfuric acid solution, 5% by weight aqueous sodium carbonate solution and water followed by concentrating to obtain 20.7 g of 6-n-propyl-2-chloroimidazo[1,2-b]pyridazine (purity: 94.0%). Yield: 99%
94% 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; toluene; xylene; at 20 - 30℃; for 2h;Product distribution / selectivity; Reference Example 1 Into a 500 mL four-necked separable flask purged with nitrogen, 20.17 g of <strong>[112581-77-8]2,6-dichloroimidazo[1,2-b]pyridazine</strong> (content: 99.2% by weight) and 190.5 g of xylene were charged to prepare a xylene solution containing <strong>[112581-77-8]2,6-dichloroimidazo[1,2-b]pyridazine</strong>. The solution obtained by mixing 4 mL of xylene and 0.22 g of 1,3-bis(diphenylphosphino)propane and 0.62 g of a toluene solution of nickel naphthenate (II) (content: 5% by weight) were mixed to prepare a solution containing a nickel catalyst. The xylene solution containing <strong>[112581-77-8]2,6-dichloroimidazo[1,2-b]pyridazine</strong> and the solution containing a nickel catalyst were mixed, and to the resultant mixture, 63.4 g of a tetrahydrofuran solution of n-propylmagnesium bromide (content: 22.2% by weight) was added dropwise over about 2 hours at an inner temperature of 20 to 30C to effect reaction. After completion of the reaction, the reaction mixture was added dropwise into a mixture of 40.4 g of 3% by weight aqueous sulfuric acid solution and 1 g of Radiolite (which was manufactured by Showa Chemical Industry Co., LTD.). After that, the resultant mixture was stirred and filtrated. The organic layer was separated from the filtrate obtained and washed twice with about 40 g of water. The organic layer after washing was concentrated to obtain 20.9 g of 6-n-propyl-2-chloroimidazo[1,2-b]pyridazine (purity: 93.2%). Yield: 94%
88.5% 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; at 0 - 20℃; for 3.16667h; <strong>[112581-77-8]2,6-Dichloroimidazo[1,2-b]pyridazine</strong> (10.0 g, 53.2 mmol) and [1,3-bis(diphenylphosphino)propane]nickel (II) dichloride (0.43 g, 0.80 mmol) were added to tetrahydrofuran (80.0 ml) under a nitrogen stream, and a solution of n-propylmagnesium bromide in tetrahydrofuran (2 M, 31.9 ml, 63.8 mmol) was added dropwise over 60 minutes to the mixture under ice-cooling. The mixture was stirred for 10 minutes under ice-cooling, and the reaction mixture was warmed to room temperature and stirred for 2 hours at room temperature. Cold water (700 ml) was added to the reaction mixture which was then acidified with conc. hydrochloric acid, and the precipitated solids were collected by filtration, and the insoluble solids were washed with dilute hydrochloric acid and then with water. On one hand, the filtrate was extracted with ethyl acetate, and the extracts were combined and washed with dilute hydrochloric acid, a saturated saline solution, an aqueous saturated sodium bicarbonate solution and a saturated saline solution in this order. The resulting organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated. The concentrated residues and the solids collected by filtration were purified by silica gel column chromatography (ethyl acetate : hexane = 3 : 7), to give the title compound as white crystals. The yield was 9.21 g (88.5%). mp 73.9-80.0C1H NMR (CDCl3, delta): 1.01(3H, t, J=7.4 Hz), 1.78(2H, m), 2.79(2H, t, J=7.6 Hz), 6.96 (1H, d, J=9.3 Hz), 7.75(1H, d, J=9.3 Hz), 7.80(1H, s). IR(Nujol, cm-1): 3122, 1466, 1377, 1314, 1302.
  • 2
  • [ 112581-77-8 ]
  • [ 2234-82-4 ]
  • [ 570416-05-6 ]
YieldReaction ConditionsOperation in experiment
48.2% 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; at 10 - 60℃; for 4h; <strong>[112581-77-8]2,6-Dichloroimidazo[1,2-b]pyridazine</strong> (1.6 g, 8.5 mmol), [1,3-bis(diphenylphosphino)propane]nickel (II) dichloride (catalytic amount) and dehydrated tetrahydrofuran (20 ml) were introduced into a 100-ml three-necked flask under a nitrogen stream and stirred under ice-cooling, and a solution of propylmagnesium chloride in tetrahydrofuran (2 M, 6.4 ml, 12.8 mmol) was added dropwise thereto at 10C or less. After dropping, the mixture was stirred for 1 hour at the same temperature, for 1 hour at room temperature and for 2 hours at 50 to 60C. After the reaction was completed, the reaction solution was left and cooled, and water (50 ml) was added thereto, and the mixture was stirred and extracted with ethyl acetate (20 ml×2). The organic layers were combined, washed with water, dried over magnesium sulfate and concentrated, and the residues were purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1) to give the title compound as orange crystals (containing a small amount of impurities). The yield was 0.8 g (48.2%). mp: not measured.1H NMR (CDCl3, delta): 1.01 (3H,t,J=7.3 Hz), 1.7-1.9 (2H,m), 2.79 (2H,t,J=7.6 Hz), 6.96 (1H,d,J=9.3 Hz), 7.75 (1H,d,J=9.3 Hz), 8.19 (1H,d,J=9.4 Hz)
 

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