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Chemical Structure| 656798-50-4 Chemical Structure| 656798-50-4

Structure of 656798-50-4

Chemical Structure| 656798-50-4

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Product Details of [ 656798-50-4 ]

CAS No. :656798-50-4
Formula : C8H6N2O2
M.W : 162.15
SMILES Code : NC1=CC=C(C#C)C=C1[N+]([O-])=O
MDL No. :MFCD11618077
InChI Key :ZYKXXTRGRCOWJO-UHFFFAOYSA-N
Pubchem ID :50998788

Safety of [ 656798-50-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 656798-50-4 ]

* 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 [ 656798-50-4 ]

[ 656798-50-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 261953-36-0 ]
  • [ 656798-50-4 ]
  • [ 947311-93-5 ]
YieldReaction ConditionsOperation in experiment
35% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) chloride; In tetrahydrofuran; at 20℃; Example 159; Synthesis of [5-(lH-Indazol-6-ylethynyl)-lH-benzoimidazol-2-yl]-(2-trifluoromethyl- phenyl)-amineA mixture of 4-bromo-2-nitrophenylamine (2.17 g, 10 mmol), ethynyltrimethyl-silane (2.11 mL, 98%, 15 mmol), dichlorobis(triphenylphosphine)palladium(II) (211 mg, 0.3 mmol) and copper(I) chloride (66.5 mg, 0.35 mmol) in THF (10 mL) and triethyl amine (10 mL) was stirred at room temperature for 3 days. The product, 2-nitro-4- trimethylsilanylethynylphenylamine was purified by silica gel column chromatography. LC-MS m/z: 235 (M+l)+. A mixture of the silyl intermediate from previous above potassium carbonate (2.76 g,20 mmol) and methanol (30 mL) was stirred for two days. Purification by silica gel column chromatography gave 4-ethynyl-2-nitrophenylamine as red solid (1.306 g, 8.05 mmol, yield81% for 2 steps). LC-MS m/z: 163 (M+l)+.A mixture of 4-ethynyl-2-nitro-phenylamine (1.306 g, 8.05 mmol), 6-iodo-lH- indazole (1.965 g, 8.05 mmol), dichlorobis(triphenylphosphine)palladium(II) (122 mg, 0.24 mmol) and copper(I) chloride (54.4 mg, 0.28 mmol) in THF (8 mL) and triethyl amine (8 mL) was stirred at room temperature overnight. Purification by column chromatography on silica <n="86"/>gel gave 4-(lH-indazol-6-ylemynyl)-2-nitrophenylamine as red solid (777 mg, 2.79 ramol, yield 35%). LC-MS m/z: 279 (M+l)+.A mixture of the nitro compound from above (774 mg, 2.78 mmol), iron powder (1.61 g, 97%, 28 mmol) and ammonium chloride (2.25 g, 42 mmol) in ethanol (1.5 mL) and water (1.5 mL) was refluxed for 6 h. Purification by column chromatography on silica gel gave 4- (lH-indazol-6-ylethynyl)-benzene-l,2-diamine as brown solid (284 mg, 1.14 mmol, yield 41%). LC-MS m/z: 249 (M+l)+.The diamine (0.3 mmol) from above was reacted with 1 -isothiocyanato-2- trifluoromethylbenzene (0.3 mmol) followed by cyclization in situ using EDC as described in general procedure B to provide [5-(lH-Indazol-6-ylethynyl)-lH-benzoimidazol-2-yl]-(2- trifluoromethylphenyl)-amine as yellow solid (178 mg, 0.426 mmol, yield 66%). LC-MS m/z: 418 (MH-I)+.
 

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