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Chemical Structure| 127566-18-1 Chemical Structure| 127566-18-1

Structure of 127566-18-1

Chemical Structure| 127566-18-1

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Product Details of [ 127566-18-1 ]

CAS No. :127566-18-1
Formula : C6H6ClN3O2
M.W : 187.58
SMILES Code : O=C(O)CN1C(C=CC(Cl)=N1)=N

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Application In Synthesis of [ 127566-18-1 ]

* 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 [ 127566-18-1 ]

[ 127566-18-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 127566-18-1 ]
  • [ 112581-77-8 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; trichlorophosphate; In chlorobenzene; at 20 - 120℃; for 6.38333h;Product distribution / selectivity; Example 4 1.88 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 99.5% by weight) was mixed with 7.52g of monochlorobenzene and 0.79 g of pyridine. To the mixture obtained, 3.84 g of phosphorus oxychloride was added dropwise over 3 minutes at an inner temperature of 20 to 40C followed by heating to an inner temperature of 120C over 20 minutes. After reacting at the same temperature for 6 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 99%.
96% Example 1 41.5 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 96. 5% by weight) was mixed with 260 g of mixed xylene. To the mixture obtained, 98.1 g of phosphorus oxychloride was added at an inner temperature of 20 to 25C over 1 hour. To the mixture obtained, 32.4 g of triethylamine was added at an inner temperature of 10 to 40C over 2 hours followed by heating to an inner temperature of 120C over 3 hours. After reacting at the same temperature for 12 hours, the mixture was cooled to an inner temperature of 80C. The reaction mixture obtained was added dropwise over 1 hour into 184.8 g of water adjusted at an inner temperature of 85C. To this, 120 g of mixed xylene was added and 48% by weight aqueous sodium hydroxide solution was added to adjust pH of an aqueous layer to 4.5. An organic layer was obtained by separation procedure, and the organic layer was washed with 83 g of 1% by weight aqueous sodium hydroxide solution and then with 83 g of water. The organic layer after washing was concentrated to obtain 39.6 g of 2,6-dichloro[1,2-b]pyridazine (content: 97.0% by weight). The yield of 2,6-dichloro[1,2-b]pyridazine was 96%.
95% With 5-ethyl-2-methyl-pyridine; trichlorophosphate; at 20 - 120℃; for 6.38333h;Product distribution / selectivity; Example 2 1.88 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 99.5% by weight) was mixed with 3.64g of 2-methyl-5-ethylpyridine. To the mixture obtained, 9.22 g of phosphorus oxychloride was added dropwise over 3 minutes at an inner temperature of 20 to 40C followed by heating to an inner temperature of 120C over 20 minutes. After reacting at the same temperature for 6 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 95%.
90% With N,N-dimethylaniline hydrochloride; trichlorophosphate; at 20 - 120℃; for 6.38333h;Product distribution / selectivity; Examples 3 According to the same manner as that described in Example 2, the reaction mixture containing 2,6-dichloroimidazo[1,2-b]pyridazine was obtained except that 4.70 g of dimethylaniline hydrochloride salt was used in place of 3.64 g of 2-methyl-5-ethylpyridine. The yield of 2,6-dichloro[1,2-b]pyridazine was 90%.
73% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In xylene; at 10 - 120℃; for 15h;Product distribution / selectivity; Example 7; To the mixture prepared by mixing 10.0 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 98% by weight) with 62.7 g of xylene, 24.0 g of phosphorus oxychloride was added dropwise at an inner temperature of 10 to 30C followed by adding dropwise 10.13 g of diisopropylethylamine at an inner temperature of 10 to 50C. The mixture obtained was heated to 120C. After reacting at the same temperature for 15 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 73%.
61 - 62% With triethylamine; trichlorophosphate; In xylene; at 10 - 120℃; for 21 - 24h;Product distribution / selectivity; Example 5 To the mixture prepared by mixing 10.0 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 98% by weight) with 62.7 g of xylene, 24.0 g of phosphorus oxychloride was added dropwise at an inner temperature of 10 to 30C followed by adding dropwise 15.8 g of triethylamine at an inner temperature of 10 to 50C. The mixture obtained was heated to 120C. After reacting at the same temperature for 21 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 61%. Example 6; To the mixture prepared by mixing 10.0 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 98% by weight) with 62.7 g of xylene, 12.0 g of phosphorus oxychloride was added dropwise at an inner temperature of 10 to 30C followed by adding dropwise 2.64 g of triethylamine at an inner temperature of 10 to 50C. The mixture obtained was heated to 120C. After reacting at the same temperature for 24 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 62%.
22% With trichlorophosphate; at 20 - 120℃; for 6.38333h;Product distribution / selectivity; Comparative Example 1 To 1.88 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 99.5% by weight), 9.22 g of phosphorus oxychloride was added dropwise over 3 minutes at an inner temperature of 20 to 40C. The mixture obtained was heated to an inner temperature of 120C over 30 minutes. After reacting at the same temperature for 6 hours, the mixture was cooled to obtain the reaction mixture containing 2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 22%.
0.4% Comparative Example 2 1.88 g of 3-imino-6-chloro-2,3-dihydropyridazine-2-acetic acid (content: 99.5% by weight) was mixed with 7.29g of 2-methyl-5-ethylpyridine. To the mixture obtained, 4.61 g of phosphorus oxychloride was added dropwise while keeping an inner temperature of 40C or less followed by heating to an inner temperature of 120C. After reacting at the same temperature for 6 hours, the mixture was cooled to obtain the reaction mixture containing.2,6-dichloro[1,2-b]pyridazine. The yield of 2,6-dichloro[1,2-b]pyridazine was 0.4%.

 

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