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Chemical Structure| 5459-50-7

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Product Details of [ 5459-50-7 ]

CAS No. :5459-50-7
Formula : C6H5IN2O2
M.W : 264.02
SMILES Code : NC1=CC([N+]([O-])=O)=CC=C1I
MDL No. :MFCD16877042
InChI Key :VKQOHFHGWCXKOA-UHFFFAOYSA-N
Pubchem ID :229959

Safety of [ 5459-50-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 5459-50-7 ]

* 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 [ 5459-50-7 ]

[ 5459-50-7 ] Synthesis Path-Downstream   1~42

  • 3
  • [ 5459-50-7 ]
  • [ 154048-77-8 ]
  • [ 154048-84-7 ]
  • 5
  • [ 99-09-2 ]
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  • [ 105752-04-3 ]
  • [ 116529-47-6 ]
  • [ 146512-89-2 ]
  • 6
  • [ 5459-50-7 ]
  • 6-Iod-3-nitro-benzoldiazoniumhydroxid-(1) [ No CAS ]
  • 7
  • [ 99-09-2 ]
  • [ 5459-50-7 ]
YieldReaction ConditionsOperation in experiment
With Iodine monochloride; In ethanol; at 20℃; 3-nitroaniline (6.9 g, 0.05 mmol) was dissolved in 150ml ethanol, iodine chloride (8.1 g, 0.05 mmol) added with dropwise. The reaction mixture was stirred at RT for 4 hours. After that, the solvents were evaporated, and the residue was extracted with EtOAc (100 mL), washed with water (50 mL) and brine (50 mL), dried over anhydrous NaSO4. After concentrated in vacuo, the residue was purified by column chromatography (PE/EtOAc =40:1→20:1) to afford the desired product (8.9 g). MS (ESI) m/e (M+H*): 265.
8.9 g With Iodine monochloride; In ethanol; at 25℃; for 4h; 3-nitroaniline (6.9 g, 0.05 mmol) was dissolved in 150 ml ethanol, iodine chloride (8.1 g, 0.05 mmol) added with dropwise. The reaction mixture was stirred at RT for 4 hours. After that, the solvents were evaporated, and the residue was extracted with EtOAc (100 mL), washed with water (50 mL) and brine (50 mL), dried over anhydrous NaSO4. After concentrated in vacuo, the residue was purified by column chromatography (PE/EtOAc=40:1→20:1) to afford the desired product (8.9 g). MS (ESI) m/e (M+H+): 265.
  • 8
  • [ 7790-99-0 ]
  • [ 64-19-7 ]
  • [ 99-09-2 ]
  • [ 5459-50-7 ]
  • [ 116529-47-6 ]
  • [ 146512-89-2 ]
  • 9
  • [ 7647-01-0 ]
  • [ 99-09-2 ]
  • potassium iodate [ No CAS ]
  • [ 5459-50-7 ]
  • [ 105752-04-3 ]
  • [ 116529-47-6 ]
  • [ 146512-89-2 ]
  • 11
  • [ 99-09-2 ]
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  • [ 146512-89-2 ]
  • 13
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  • [ 355839-49-5 ]
  • [ 808145-75-7 ]
  • 14
  • [ 5459-50-7 ]
  • [ 192314-71-9 ]
  • (2S)-2-(di-tert-butoxycarbonylamino)-3-(6-nitro-1H-indol-3-yl)propionic acid methyl ester [ No CAS ]
  • 15
  • [ 709-49-9 ]
  • [ 5459-50-7 ]
  • [ 105752-04-3 ]
  • 16
  • [ 5459-50-7 ]
  • [ 943975-78-8 ]
  • [ 943975-79-9 ]
  • 17
  • [ 5459-50-7 ]
  • [ 504-02-9 ]
  • C12H11IN2O3 [ No CAS ]
  • 18
  • [ 5459-50-7 ]
  • [ 536-74-3 ]
  • 5-nitro-2-(phenylethynyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile;Inert atmosphere; Reflux; General procedure: PdCl2(PPh3)2 (35.1 mg, 0.05 mmol), CuI (9.5 mg, 0.05 mmol), PPh3 (13.1 mg, 0.05 mmol) and iodoaniline derivatives (1.00 mmol) were stirred under N2 in a mixed solvent with CH3CN (5 mL) and Et3N (1 mL). The alkyne (1.20 mmol) was added to the mixture and stirred in reflux. The reaction was monitored by TLC. After completion, H2O (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over anhydrous MgSO4, concentrated at the reduced pressure. And the crude product was purified by column chromatography to give 2-alkynylanilines.
  • 19
  • [ 5459-50-7 ]
  • 7-nitro-2,3-dihydro-1H-carbazole-4(9H)-one [ No CAS ]
  • 20
  • [ 5459-50-7 ]
  • [ 943975-93-7 ]
  • 21
  • [ 5459-50-7 ]
  • [ 854443-88-2 ]
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  • [ 854443-93-9 ]
  • 23
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  • [ 943975-82-4 ]
  • 24
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  • [ 943975-91-5 ]
  • 25
  • [ 5459-50-7 ]
  • C42H38N4O10Cl4 [ No CAS ]
  • 26
  • [ 5459-50-7 ]
  • [ 943975-92-6 ]
  • 27
  • [ 5459-50-7 ]
  • [ 943975-80-2 ]
  • 28
  • [ 5459-50-7 ]
  • C27H38N2O8 [ No CAS ]
  • 29
  • [ 5459-50-7 ]
  • [ 943975-81-3 ]
  • 31
  • [ 5459-50-7 ]
  • [ 56937-50-9 ]
  • 32
  • [ 5459-50-7 ]
  • [ 808145-80-4 ]
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  • [ 808145-77-9 ]
  • 34
  • [ 5459-50-7 ]
  • [ 2996-30-7 ]
  • 35
  • [ 5459-50-7 ]
  • [ 129241-89-0 ]
  • C25H35N3O8 [ No CAS ]
  • 36
  • [ 35447-83-7 ]
  • [ 5459-50-7 ]
  • [ 1246471-66-8 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of 4-ethynylacetanilide (800 mg, 3.1 mmol) in anhydrousTHF (6 ml) was added compound 2 (0.5 g, 3.1 mmol), PdCl2(PPh)3 (33 mg, 0.05 mmol), CuI (10 mg, 0.05 mmol) and TEA (2 mL). The mixture was protected from light and stirred at RT overnight. The resulting solution was concentrated in vacuo, and the residue was washed with DCM to give the desired compound (300 mg) as a yellow solid. MS (ESI) m/e (M+H+): 296.
300 mg With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 25℃; To a stirred solution of 4-ethynylacetanilide (800 mg, 3.1 mmol) in anhydrous THF (6 ml) was added compound 2 (0.5 g, 3.1 mmol), PdCl2(PPh)3 (33 mg, 0.05 mmol), CuI (10 mg, 0.05 mmol) and TEA (2 mL). The mixture was protected from light and stirred at RT overnight. The resulting solution was concentrated in vacuo, and the residue was washed with DCM to give the desired compound (300 mg) as a yellow solid. MS (ESI) m/e (M+H+): 296.
  • 37
  • [ 70933-58-3 ]
  • [ 5459-50-7 ]
  • [ 1246471-71-5 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; 3-Ethynylacetanilide (480 mg, 3 mmol) and 2-iodo-5-introaniline (800 mg, 3 mmol) were dissolved in anhydrous THF (30 mL), PdCl2(PPh3)2 (105 mg,0.15 mmol) and CuI (28.5 mg,0.15 mmol) Et3N(I ml) was added sequentially. The reaction mixture was protected by N2 and stirred at RT for overnight. After that, the solvents were evaporated, and the residue was extracted with EtOAc (50x2 mL), washed with water (40 mL) and brine (30 mL), dried over anhydrous NaSO4. After concentrated in vacuo, the residue was purified by column chromatography (DCM/MeOH =50: l→20:l) to afford the desired product (620 mg). MS (ESI) m/e (M+H*): 296.
620 mg With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 25℃;Inert atmosphere; 3-Ethynylacetanilide (480 mg, 3 mmol) and 2-iodo-5-introaniline (800 mg, 3 mmol) were dissolved in anhydrous THF (30 mL), PdCl2(PPh3)2 (105 mg,0.15 mmol) and CuI (28.5 mg,0.15 mmol) Et3N (1 ml) was added sequentially. The reaction mixture was protected by N2 and stirred at RT for overnight. After that, the solvents were evaporated, and the residue was extracted with EtOAc (50×2 mL), washed with water (40 mL) and brine (30 mL), dried over anhydrous NaSO4. After concentrated in vacuo, the residue was purified by column chromatography (DCM/MeOH=50:1→20:1) to afford the desired product (620 mg). MS (ESI) m/e (M+H+): 296.
  • 38
  • [ 99-09-2 ]
  • [ 5459-50-7 ]
  • [ 105752-04-3 ]
  • 2-iodo-3-nitro-aniline [ No CAS ]
  • 39
  • [ 99-09-2 ]
  • [ 5459-50-7 ]
  • 2-iodo-3-nitro-aniline [ No CAS ]
  • 40
  • [ 124-13-0 ]
  • [ 5459-50-7 ]
  • 3-hexyl-6-nitro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% General procedure: to ortho iodoaniline,1(a-q) (0.10 mmol), in dioxane (5 mL) was added PdCl2 (5 mol %), A-taphos(10 mol %). The solution was purged with nitrogen and stirred at roomtemperature for 10 min and aldehyde (2a-q) (0.16 mmol), CH3COOCs(0.20 mmol), were added. The reaction mixture was again purged withnitrogen and heated in the microwave at 120 C for 30-40 min. Reaction wasmonitored by TLC. After the completion, reaction mixture was cooled to roomtemperature and water was added to the reaction mixture. It was thenextracted with ethyl acetate (25 mL 2) and the separated organic layer wasdried over anhydrous Na2SO4. The organic layer was filtered and concentratedunder vacuum, and the residue was purified by flash column chromatographyon silica gel.
  • 41
  • 4-(1H-indol-3-yl)butanal [ No CAS ]
  • [ 5459-50-7 ]
  • [ 1476806-90-2 ]
YieldReaction ConditionsOperation in experiment
40 mg With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; In N,N-dimethyl-formamide; at 85℃; for 20h;Sealed tube; Inert atmosphere; General procedure: A quantitativeyield for the oxidation step (8→5)16 is presumed and hencethe molar amounts of each reagent are based on alcohol 8. Asealed tube charged with DMF (1-2 mL) was degassed withnitrogen for 30 min. Freshly prepared aldehyde 5 (0.15-0.26mmol) was added, followed by the appropriate o-iodoaniline6a-i (0.17-0.29 mmol), DABCO (0.45-0.79 mmol) andPd(OAc)2 (5 mol%). The tube was then sealed under ablanket of nitrogen and stirred at 85 C for 18-90 h. Thecooled solution was poured onto H2O (10 mL) and extractedwith Et2O (3 × 10 mL). The combined organic extracts weredried (MgSO4), filtered, and concentrated in vacuo.Purification by flash chromatography on silica gel (hexanes-EtOAc) gave the desired products 1a-i, the yields of whichwere calculated over two steps from alcohol 8.
  • 42
  • [ 234084-69-6 ]
  • [ 5459-50-7 ]
  • [ 1589523-05-6 ]
 

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