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[ CAS No. 14628-34-3 ] {[proInfo.proName]}

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Chemical Structure| 14628-34-3
Chemical Structure| 14628-34-3
Structure of 14628-34-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 14628-34-3 ]

CAS No. :14628-34-3 MDL No. :MFCD26401610
Formula : C5H5ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :RNUMDSZAIHARFX-UHFFFAOYSA-N
M.W : 144.56 Pubchem ID :12910144
Synonyms :

Safety of [ 14628-34-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14628-34-3 ]

* 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 [ 14628-34-3 ]

[ 14628-34-3 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 908094-01-9 ]
  • [ 14628-34-3 ]
  • [ 40995-48-0 ]
  • [ 40995-50-4 ]
  • 2
  • [ 14628-34-3 ]
  • [ 100-79-8 ]
  • [ 98700-57-3 ]
  • 3
  • [ 194861-99-9 ]
  • [ 14628-34-3 ]
  • 5-<(3-tert-Butyl-2-phenyl-1,3-oxazolidin-5-yl)methoxy>-2-methylpyridazin-3(2H)-one [ No CAS ]
  • 4
  • [ 91757-10-7 ]
  • [ 14628-34-3 ]
  • [ 87633-93-0 ]
  • 6
  • [ 14628-34-3 ]
  • [ 98700-69-7 ]
  • 7
  • [ 14628-34-3 ]
  • [ 104949-35-1 ]
  • 8
  • [ 14628-34-3 ]
  • [ 87633-91-8 ]
  • 9
  • [ 73746-45-9 ]
  • [ 14628-34-3 ]
  • [ 1262423-41-5 ]
YieldReaction ConditionsOperation in experiment
71% With caesium carbonate; In N,N-dimethyl-formamide; at 45 - 65℃; for 3.5h; b) 5-(4-iodo-2-methyl-imidazol-1-yl)-2-methyl-2H-pyridazin-3-oneTo a solution of 160 mg (1.11 mmol) of 5-chloro-2-methyl-2H-pyridazin-3-one (CAS: [14628-34-3]), 230 mg (1.11 mmol) of <strong>[73746-45-9]4-iodo-2-methyl-1H-imidazole</strong> (CAS: [73746-45-9]), in 3.5 ml of dry DMF were added 721 mg (2.21 mmol) of cesium carbonate. The suspension was stirred for 30 min at 45 C., then for 3 h at 65 C. and allowed to cool. The cristallised product is filtered off, washed with ethyl acetate and dried in vaccuo to yield 250 mg (0.791 mmol, 71%) of the title compound as a crystalline light yellow solid, MS: m/e=316.9 (M+H+).
71% With caesium carbonate; In N,N-dimethyl-formamide; at 45 - 60℃; for 3.5h;Product distribution / selectivity; To a solution of 160 mg (1.11 mmol) of 5-chloro-2-methyl-2H-pyridazin-3-one (CAS: [14628- 34-3]), 230 mg (1.11 mmol) of 4-iodo-2-methyl-lH-imidazole (CAS: [73746-45-9]), in 3.5 ml of dry DMF were added 721 mg (2.21 mmol) of cesium carbonate. The suspension was stirred for 30 min at 45C, then for 3h at 65C and allowed to cool. The cristallised product is filtered off, washed with ethyl acetate and dried in vaccuo to yield 250 mg (0.791 mmol, 71%) of the title compound as a crystalline light yellow solid, MS: m/e = 316.9 (M+H+).
  • 10
  • [ 14628-58-1 ]
  • [ 14628-34-3 ]
YieldReaction ConditionsOperation in experiment
58% c) 5-chloro-2-methyl-2H-pyridazin-3-one A mixture of 1.50 g (10.70 mmol) of 5-methoxy-2-methyl-2H-pyridazin-3-one and 7.8 ml (13.1 g, 85.6 mmol) of phosphorus oxychloride was heated at 110 C. for 2 h. After allowing to cool to room temperature, the mixture was poured into 100 ml of ice/water with vigourous stirring. After neutralization by addition of saturated sodium carbonate solution, the compound was worked up with methylene chloride/water, dried over magnesium sulfate and concentrated in vaccuo. The crude material was purified by flash chromatography on silicagel using a 80:20 mixture of ethyl acetate and heptane as eluant to yield 904 mg (6.25 mmol, 58%) of the title compound as a crystalline white solid, MS: 141.2 (M+H+).
58% A mixture of 1.50 g (10.70 mmol) of 5-methoxy-2-methyl-2H-pyridazin-3-one and 7.8 ml (13.1 g, 85.6 mmol) of phosphorus oxychloride was heated at 1100C for 2h. After allowing to cool to room temperature, the mixture was poured into 100 ml of ice/water with vigourous stirring. After neutralization by addition of saturated sodium carbonate solution, the compound was worked up with methylene chloride/water, dried over magnesium sulfate and concentrated in vaccuo. The crude material was purified by flash chromatography on silicagel using a 80:20 mixture of ethyl acetate and heptane as eluant to yield 904 mg (6.25 mmol, 58%) of the title compound as a crystalline white solid, MS: 141.2(M+H+).
  • 11
  • [ 933-76-6 ]
  • [ 14628-34-3 ]
YieldReaction ConditionsOperation in experiment
414 mg With hydrogen iodide; In water; for 12h;Reflux; Step 1: 5-Chloro-2-methylpyridazin-3(2H)-one 4,5-Dichloro-2-methylpyridazin-3(2H)-one (1 g) is dissolved in aqueous HI solution (57%, 8.5 mL) and the mixture is heated to reflux for 12 hours. After cooling to room temperature the mixture is treated with aqueous Na2S2O3 solution (30%, 100 mL) and stirred for 1 hour. The mixture is then extracted three times with dichloromethane. The combined organic phases are washed with brine, dried (MgSO4) and concentrated. The residue is triturated with diisopropylether. Yield: 414 mg; Mass spectrum (ESI+): m/z=145 [M+H]+.
414 mg With hydrogen iodide; for 12h;Reflux; 4,5-Dichloro-2-methylpyridazin-3(2H)-one (1 g) is dissolved in aqueous HI solution (57 %, 8.5 mL) and the mixture is heated to reflux for 12 hours. After cooling to room temperature the mixture is treated with aqueous Na2S2O3 solution (30 %, 100 mL) and stirrd for 1 hour. The mixture is then extracted three times with dichloromethane. The com bined organ ic phases are washed with bri ne, d ried (MgSO4) and concentrated. The resudue is triturated with diisopropylether. Yield: 414 mg; Mass spectrum (ESI+): m/z = 145 [M+H]+.
  • 12
  • [ 14628-57-0 ]
  • [ 14628-34-3 ]
  • 13
  • [ 14628-34-3 ]
  • [ 1262422-95-6 ]
  • 14
  • [ 1004761-68-5 ]
  • [ 14628-34-3 ]
  • [ 1458655-56-5 ]
YieldReaction ConditionsOperation in experiment
2.6 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 60℃; for 12h;Inert atmosphere; Sealed tube; Step 2: 5-(4-Amino-3,5-dimethylphenyl)-2-methylpyridazin-3(2H)-one [0781] The title compound is prepared from <strong>[14628-34-3]5-chloro-2-methylpyridazin-3(2H)-one</strong> and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline following a procedure analogous to that described in Step 2 of Intermediate 62. The mixture is stirred for 12 hours at 60 C. LC (method 9): tR=0.79 min; Mass spectrum (ESI+): m/z=230 [M+H]+.
  • 15
  • [ 14628-34-3 ]
  • [ 73183-34-3 ]
  • [ 1527525-02-5 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos; In 1,4-dioxane; at 90℃; for 2h;Sealed tube; Inert atmosphere; To a mixture of 5-chloro-2-methyl-pyridazin-3-one (3.560 mmol; 514.7 mg), bis(pinacolato)diboron (5.687 mmol; 1459 mg) and potassium acetate (7.121 mmol; 720.5 mg) in 1,4-Dioxane (12 mL) in a pressure tube under Nitrogen was added X-PHOS (0.4273 mmol; 142.3 mg) and tris(dibenzylideneacetone)dipalladium(0); (0.1780 mmol; 163.0 mg). The tubewas sealed and heated at 90C for 2h. The reaction mixture was filtered hot through Celite. The filter cake was washed with EtOAc. The filtrated washed with water, and brine. The organic layer was dried with MgSO4, and then concentrated to afford 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazin-3-one, which was used without further purification.
  • 16
  • 5-chloropyridazin-3(2H)-one [ No CAS ]
  • [ 74-88-4 ]
  • [ 14628-34-3 ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; A solution of 4-chloro-1H-pyridazin-6-one ( 6.000 mmol; 783.2 mg), lodomethane(7.200 mmol; 1032 mg; 0.453 mL), and potassium carbonate (9.000 mmol; 1256 mg) in DMF(12 mL) was stirred at room temperature overnight. The mixture was filtered. The filtrate was partitioned between EtOAc and water. The organic layer was concentrated. The residue was purified on silica eluted with 0 to 40% EtOAc in DCM to afford 5-chloro-2-methyl-pyridazin-3-one as an off-white solid (514.7, 59%).
  • 17
  • [ 14628-34-3 ]
  • [ 1527522-55-9 ]
  • 18
  • potassium trifluoro(2-methyl-4-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-5-yl)borate [ No CAS ]
  • [ 14628-34-3 ]
  • [ 1611464-59-5 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In tetrahydrofuran; water; at 80℃; for 16h; Example 135 Step A : 2-methyl-5-(2-methyl-4-(((lS,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy) pyrimidin-5-yl)pyridazin-3(2H)-one A mixture of potassium trifluoro(2-methyl-4-(((lS,2S)-2-(5-methylpyridin-2- yl)cyclopropyl)methoxy)pyrimidin-5-yl)borate (100 mg, 0.28 mmol), 5-chloro-2- methylpyridazin-3(2H)-one (made according to WO2011/6910 Al, 48 mg, 0.34 mmol), [1,1'- bis(diphenylphosphino) ferrocene] dichloropalladium(II) (23 mg, 0.03 mmol) and cesium carbonate (274 mg, 0.84 mmol) in THF (1.7 mL) and H20 (0.8 mL) was stirred at 80 C for 16 h. The mixture was cooled to ambient temperature, diluted with EtOAc (5 mL), washed with sodium bicarbonate (2 mL) and brine (2 mL), dried over MgS04, filtered and concentrated. The residue was purified by reverse phase chromatography (Waters Sunfire CI 8 OBD 5-80% methanol in water with 0.1% H3' FLO modifer) to give the title compound: LC/MS m/z = 364.1 [M+H]+; NMR (400 MHz, MeOD) δ 8.57 (s, 1 H), 8.20 (d, 2 H), 7.50 (d, 1 H), 7.20 (s, 1 H), 7.15 (d, 1 H), 4.63 - 4.58 (m, 1 H), 4.52 - 4.47 (m, 1 H), 3.79 (s, 3 H), 2.63 (s, 3 H), 2.16 (s, 3 H), 2.28 - 2.15 (m, 1 H), 1.86 (s, 1 H), 1.34 - 1.13 (m, 1 H), 1.13 - 1.11 (m, 1 H).
  • 19
  • 5-chloropyridazin-3(2H)-one [ No CAS ]
  • [ 18107-18-1 ]
  • [ 14628-34-3 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; at 0 - 20℃; for 65h; Step A: 5-Chloro-2-methylpyridazin-3(2H)-one A solution of 5-chloropyridazin-3(2H)-one (1 g, 7.66 mmol) in CH2C12 (20 mL) and MeOH (4.00 mL) was cooled to 0 C, trimethylsilyldiazomethane (8 mL, 16.00 mmol) was added and the resulting mixture was stirred for 1 h. The reaction mixture was wanned to room temperature and stirred for 64 h. It was quenched with acetic acid (1 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (ISCO Combiflash, Gold 40 g, 0-50% EtOAc in hexanes) to give 5-chloro-2-methylpyridazin-3(2H)-one, as a white solid. LCMS calc. = 145.02; found = 145.00 (M+H)+. NMR (500 MHz, CDC13): δ 7.72 (d, J= 2.4 Hz, 1 H); 6.97 (d, J= 2.4 Hz, 1 H); 3.76 (s, 3 H).
  • 20
  • [ 4522-35-4 ]
  • [ 14628-34-3 ]
  • [ 1621525-40-3 ]
YieldReaction ConditionsOperation in experiment
Step B: 5-(3-Iodo-lH-pyrazol-l-yl)-2-methylpyridazin-3(2 /)-one To a clean dry flask was added sodium hydride (200 mg, 5.00 mmol) and anhydrous NMP (10 mL). The mixture was cooled to 0 C. 3-Iodopyrazole (959 mg, 4.95 mmol) was added to the mixture in one portion. The mixture was stirred for 10 min at room temperature, then 5-chloro-2-methylpyridazin-3(2H)-one (650 mg, 4.50 mmol) was added in one portion. The mixture was stirred at 100 C for 2 h. The reaction mixture was cooled to room temperature, water (100 mL) was added, and the resulting mixture was extracted with EtOAc (100 mL). The organic layer was washed with water (3 x 50 mL) and the combined aqueous layers were extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (ISCO Combiflash, 40 g, 0-100% EtOAc in hexanes) to give 5-(3-iodo-lH-pyrazol-l-yl)-2-methylpyridazin-3(2H)-one, as a white solid. LCMS calc. = 302.97; found = 302.95 (Mu+Eta)+. NMR (500 MHz, CDC13): delta 8.47 (d, J = 2.6 Hz, 1 H); 7.79-7.74 (d, J = 2.6 Hz, 1 H); 6.93 (d, J = 2.6 Hz, 1 H); 6.74 (d, J = 2.6 Hz, 1 H); 3.84 (s, 3 H).
  • 21
  • [ 40636-99-5 ]
  • [ 60-34-4 ]
  • [ 14628-34-3 ]
YieldReaction ConditionsOperation in experiment
70% With acetic acid; for 3h;Reflux; 13.4 g of <strong>[40636-99-5]4-chloro-5-hydroxy-5H-furan-2-one</strong> and 4.6 g of methylhydrazine were added to 40 mL of iceAcid, heated to reflux for 3 hours. After completion of the reaction, the reaction solution was poured into 40 mL of water. The pH of the solution was adjusted with NaHC03 to pH 7-8, and finally extracted three times with ethyl acetate (3 * 25 mL). The resulting ethyl acetate phase was dried over anhydrous sodium sulfate and finally concentrated toDry, get 10. lg final product, the yield of 70%.
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