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CAS No. : | 5044-38-2 | MDL No. : | MFCD00047067 |
Formula : | C10H8ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 177.63 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) iodide; N-hydroxyphthalimide; sodium methylate In dimethyl sulfoxide at 90℃; for 12h; | |
94% | With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; | |
88% | With [Cu8(H){S2P(OiPr)2}6](PF6); caesium carbonate at 105℃; for 24h; |
88% | With 4.5Cu(2+)*4.5Ni(2+)*9C16H12N2*6C2O4(2-)*6H2O*P2W18O62(6-); sodium hydroxide In dimethyl sulfoxide at 120℃; for 12h; | |
87% | With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 24h; Inert atmosphere; Schlenk technique; | General procedure 1: Synthesis of N-aryl pyrroles General procedure: An oven-dried Schlenk tube was charged with Cu(OAc)2·H2O (0.1 mmol, 0.01 equiv), Cs2CO3(20 mmol, 2 equiv), and aryl iodide (if solid, 12 mmol, 1.2 equiv). The tube was degassed with argon for three times. Then DMF (20 mL), pyrrole (10 mmol, 1 equiv), and aryl iodide (if liquid,12 mmol, 1.2 equiv) were added via syringe under room temperature. The mixture was stirred at110 °C for 24 h, and then cooled down to room temperature. The reaction mixture was quenched with water (40 mL) and extracted with ethyl ether (20 mL) for three times. The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude products were purified using flash column chromatography on silica gel to afford the desired product. |
86% | With dimethylenecyclourethane; copper(l) iodide; sodium methylate In dimethyl sulfoxide at 80℃; for 8h; | |
83% | With copper(l) iodide; N-[phenyl(acetylamino)methyl]acetamide; sodium methylate In dimethyl sulfoxide at 130℃; for 12h; | |
83% | With tetramethyl ammoniumhydroxide; ethyl 2-oxocyclohexane carboxylate; copper(l) chloride In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; | |
82% | With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In tetrahydrofuran at 60℃; for 18 - 24h; Inert atmosphere; | |
80% | With sodium hydroxide; copper(l) iodide; tetrabutylammomium bromide In toluene for 22h; Heating; | |
79% | With copper(l) iodide; (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one; caesium carbonate In acetonitrile at 82℃; for 12h; Inert atmosphere; | |
75% | With copper(l) iodide; C37H56N4O4; caesium carbonate In 1,2-dimethoxyethane at 80℃; for 20h; Inert atmosphere; Sealed tube; chemoselective reaction; | |
72% | With tetra(n-butyl)ammonium hydroxide; copper(l) chloride In water at 80℃; for 24h; Inert atmosphere; | |
72% | With MOF-199; sodium hydroxide In dimethyl sulfoxide at 120℃; for 12h; Sealed tube; | |
67% | With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 25 - 30℃; for 14h; | |
62% | With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 100℃; for 24h; | General procedure for N-arylation of nitrogen nucleophiles General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis. |
60% | With copper(ll) sulfate pentahydrate; sodium hydroxide In dimethyl sulfoxide at 110℃; for 12h; Sealed tube; | N-arylation of pyrrole: General procedure: CuSO4·5H2O (12.50 mg, 0.05 mmol), the aryl iodide or bromide(1.0 mmol), pyrrole (1.5 mmol), NaOH (80 mg, 2 mmol), and DMSO(2 mL) were placed in a 10 mL sealed tube. The mixture was heatedat 110 °C in a preheated oil bath for 12 h. It was then cooled to roomtemperature, diluted with 20 mL H2O, and the mixture was extractedwith ethyl acetate (3 × 20 mL). The combined organic phases waswashed with water and brine, dried over anhydrous Na2SO4, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel (ethyl acetate/petroleum ether, 1 : 100)to afford the target products. All C-N coupling products reported hereare known products and were characterised by GC-MS and 1H NMR,which were compared with the previously reported dates. |
52% | With copper(I) oxide; potassium phosphate; tetrabutylammomium bromide In water at 130℃; for 24h; Closed system; | General procedure for N-arylation of amines:The N-nucleophile (1.47 mmol), Cu2O (Sigma-Aldrich, 99.99% purity, 0.147 mmol), K3PO4 (2.94 mmol), the aryl halide (1.76 mmol), phase transfer catalyst (0.147 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 130 °C for 24 h, then the heterogeneous mixture was cooled to RT and diluted with dichloromethane. The resulting solution was directly filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of all products was confirmed by 1H and 13C NMR spectroscopic analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With methanesulfonato tri(tert-butyl)phosphine (2'-amino-1,1‘-biphenyl-2-yl) palladium (II); potassium carbonate In water; toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; | |
74% | With n-BuPAd2; caesium carbonate In water; toluene at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium diacetate; sodium carbonate; ruphos In ethanol at 85℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; | General procedure for the synthesis of N-aryl pyrroles. General procedure: to a stirred solution of iodo benzene (1.0 mmol) and trans-4-hydroxy-L-proline (2.0 equiv) in dry DMSO (3.0 mL) at rt was added CuI (20 mol %) followed by Cs2CO3 (2.5 equiv) and heated at 110 °C for 24 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation; | |
87% | With copper acetylacetonate; N<SUP>1</SUP>-(4-hydroxy-2,6-dimethylphenyl)-N<SUP>2</SUP>-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere; |
Tags: 5044-38-2 synthesis path| 5044-38-2 SDS| 5044-38-2 COA| 5044-38-2 purity| 5044-38-2 application| 5044-38-2 NMR| 5044-38-2 COA| 5044-38-2 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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