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Chemical Structure| 160664-95-9 Chemical Structure| 160664-95-9

Structure of 160664-95-9

Chemical Structure| 160664-95-9

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Product Details of [ 160664-95-9 ]

CAS No. :160664-95-9
Formula : C6H9N3O
M.W : 139.16
SMILES Code : COC1=NC=C(NN)C=C1
MDL No. :MFCD09263636
InChI Key :SRQWKLIXHJRVSG-UHFFFAOYSA-N
Pubchem ID :22217853

Safety of [ 160664-95-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 160664-95-9 ]

* 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 [ 160664-95-9 ]

[ 160664-95-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 160664-95-9 ]
  • [ 179543-88-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; [Referential Example 1] ;5-Hydrazino-2-methoxypyridine hydrochloride; [] A solution of sodium nitrite (3.795 g) in water (20 mL) was added dropwise to 5-amino-2-methoxypyridine (6.21 g) in concentrated hydrochloric acid (50 mL) over a period of 60 minutes with ice cooling, and the resultant mixture was stirred at a constant temperature for 30 minutes. Tin(II) chloride dihydrate (39.5 g) in concentrated hydrochloric acid (30 mL) was added dropwise to the reaction mixture at an internal temperature of about 10C for 30 minutes, followed by stirring for 2 hours at room temperature. Under cooling with ice, the reaction mixture was partitioned between sodium hydroxide (75 g) in water (300 mL) and diethyl ether. The aqueous layer was extracted with diethyl ether twice. Subsequently, the aqueous layer was saturated with sodium chloride, followed by extraction with diethyl ether. The organic layers were combined, and dried over sodium sulfate anhydrate, followed by filtration. 1M HCl in ethanol (50 mL) was added to the filtrate and the mixture was stirred. The solid that precipitated was collected by filtration, washed with diethyl ether, and dried, to thereby give the title compound (5.02 g, 57%).1H-NMR(400MHz,DMSO-d6)delta: 3.81(3H,s), 6.82(1H,d,J=8.8Hz), 7.57 (1H, dd, J=8.8,2.9Hz) , 7.97 (1H, d, J=2.9Hz) , 8.55-9.20 (1H, br) , 10.13-10.50(3H,br). MS(ESI)m/z: 140(M+H)+.
  • 2
  • [ 179543-88-5 ]
  • [ 160664-95-9 ]
YieldReaction ConditionsOperation in experiment
60% Referential Example 2];5-Hydrazino-2-methoxypyridine; [] Sodium nitrite (3.795 g) in water (20 mL) was added dropwise to 5-amino-2-methoxypyridine (6.207 g) in concentrated hydrochloric acid (50 mL) for 80 minutes with ice cooling, followed by stirring at a constant temperature for 30 minutes. Tin(II) chloride dihydrate (39.5 g) in concentrated hydrochloric acid (30 mL) was added dropwise to the reaction mixture at an internal temperature of about 10C for 60 minutes, followed by stirring at room temperature for 12.5 hours. Under cooling with ice, sodium hydroxide (54 g) in water (200 mL) and chloroform were added to the reaction mixture. After insoluble substances in the resultant mixture were removed by filtration, the mixture was partitioned. The aqueous layer was extracted with chloroform twice. The organic layers were combined, and dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, to thereby give the title compound as crystals (4.23 g, 60%) .1H-NMR (400MHz, CDCl3) delta: 3.50-3.68(2H,br), 3.88(3H,s), 4.86-5.03 (1H, br) , 6.66(1H,d,J=8.8Hz), 7.20 (1H, dd, J=8.8, 2.9Hz), 7.77 (1H, d, J=2.9Hz). MS(ESI)m/z: 140 (M+H)+.
  • 3
  • [ 160664-95-9 ]
  • [ 50607-30-2 ]
  • 6-methoxy-1,2,3,9-tetrahydro-3,5,9-triazafluoren-4-one [ No CAS ]
  • 4
  • [ 160664-95-9 ]
  • [ 21168-41-2 ]
  • 8-chloro-2-(6-methoxypyridin-3-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With triethylamine; In 5,5-dimethyl-1,3-cyclohexadiene; at 138℃; for 2h; A mixture of ethyl-4,6-dichloro-7-methoxy-3-carboxylate DK- I-35-1 (2 g, 7.4 mmol), 5-hydrazinyl-2-methoxypyridine DK-I-82-3 (1.24 g, 8.9 mmol), triethylamine (0.90 g, 8.9 mmol) and xylenes (16 mL) was heated to reflux (138 oC) and held at reflux for 2 h. The resulting yellow-orange slurry was cooled to 100 oC and diluted with ethanol (16 mL). The reaction mixture was then refluxed at 80 oC for 30 min and then cooled to 20-25 oC. The solids were collected by filtration and washed twice with a 1:1 mixture of ethanol (2.5 mL x 2) and hexanes (2.5 mL x 2) and then washed twice with hexanes (5 mL x 2). The solid was dried to afford the product as a yellow powder DK-II-18-1 (1.0 g, 41.0%): 1H NMR (300 MHz, DMSO) delta 12.96 (s, 1H), 8.92 (d, J = 2.6 Hz, 1H), 8.77 (s, 1H), 8.42 (dd, J = 8.9, 2.6 Hz, 1H), 8.14 (s, 1H), 7.89- 7.60 (m, 2H), 6.93 (d, J = 9.0 Hz, 1H), 3.89 (s, 3H); 13C NMR (75 MHz, DMSO) delta 161.62, 160.64, 142.70, 140.12, 137.57, 134.58, 131.66, 131.15, 130.92, 130.64, 122.11, 121.58, 120.38, 110.59, 106.25, 53.74; HRMS m/z calculated for C16H12ClN4O2 (M+H)+ 327.0649 found 327.25.
 

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