Structure of 1203-41-4
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CAS No. : | 1203-41-4 |
Formula : | C13H13N |
M.W : | 183.25 |
SMILES Code : | NC1=CC=CC=C1C2=CC=CC=C2C |
MDL No. : | MFCD06739417 |
GHS Pictogram: |
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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 |
* 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 |
---|---|---|
84.8% | With potassium carbonate; triphenylphosphine;palladium diacetate; In 1,2-dimethoxyethane; ethyl acetate; | Step 1: Synthesis of 2-amino-2'-methyl-biphenyl Added together 2-methylphenyl boronic acid (24.7 g, 181 mmol), 2-bromo aniline (25.7 g, 151 mmol), palladium(II)acetate (0.85 g, 3.78 mmol), triphenylphosphine (4.0 g, 15.1 mmol), a 2 M solution of potassium carbonate (204 mL) and ethylene glycol dimethyl ether (223 mL) and heated the reaction mixture at reflux for 18 hours. After the reaction was cooled to room temperature, the aqueous phase was separated from the organic phase. The aqueous phase was extracted with ethyl acetate and the organic extractions were combined, dried over magnesium sulfate and filtered. The crude product was purified by silica gel column chromatography using 10% ethyl acetate in hexanes as the eluants. The pure fractions were collected, combined and concentrated to give 2-amino-2'-methyl-biphenyl (23.5 g, 84.8% yield) whose structure was confirmed by GCMS and NMR. |
84.8% | With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; for 18h;Reflux; | Step 1: Synthesis of 2-amino-2?-methyl-biphenyl Added together 2-methylphenyl boronic acid (24.7 g, 181 mmol), 2-bromo aniline (25.7 g, 151 mmol), palladium(II)acetate (0.85 g, 3.78 mmol), triphenylphosphine (4.0 g, 15.1 mmol), a 2 M solution of potassium carbonate (204 mL) and ethylene glycol dimethyl ether (223 mL) and heated the reaction mixture at reflux for 18 hours. After the reaction was cooled to room temperature, the aqueous phase was separated from the organic phase. The aqueous phase was extracted with ethyl acetate and the organic extractions were combined, dried over magnesium sulfate and filtered. The crude product was purified by silica gel column chromatography using 10% ethyl acetate in hexanes as the eluants. The pure fractions were collected, combined and concentrated to give 2-amino-2?-methyl-biphenyl (23.5 g, 84.8% yield) whose structure was confirmed by GCMS and NMR. |
84.8% | With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; for 18h;Reflux; | Step 1: Synthesis of 2-Amino-2'-methyl-biphenyl 2-methylphenyl boronic acid (24.7 g, 181 mmol), 2-bromoaniline (25.7 g, 151 mmol), palladium (II) acetate (0.85 g, 3.78 mmol), triphenylphosphine (4.0 g, 15.1 mmol) and added to a 2 M solution of potassium carbonate (204 ) and ethylene glycol dimethyl ether (223) together, and the reaction mixture was heated to reflux for 18 hours. After cooling the reaction to room temperature and separating the aqueous phase from the organic phase. The aqueous phase was extracted with ethyl acetate, the organic extracts were combined, dried over magnesium sulfate, and filtered. And the crude product was used as an eluent of 10% ethyl acetate in hexane was purified by silica gel column chromatography. The pure fractions were combined and collected, and concentrated to which 2-amino-2'-methyl-biphenyl-gain (23.5 g, 84.8% yield), its structure was confirmed by GCMS and NMR. |
62% | With C20H12N2O8PdS2(2-)*2Na(1+); sodium hydroxide; In water; at 100℃; for 3h; | General procedure: A solution of aryl bromide (0.5 mmol), arylboronic acid (0.75 mmol), NaOH (1.0 mmol), and complex 1 (0.5 mol %) in H2O (1.0 mL) was stirred at 100 C for 5 h. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (3 × 10 mL). The combined EtOAc extracts were dried over anhydrous Na2SO4, filtrated, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products. |
29.5% | With Supported Pd(OAc)2(PPh3)2 Over Mixed Magnesium Hydroxide and Cerium Carbonate Hydroxide Composite; In water; at 79.84℃; for 2h; | General procedure: A typical procedure for Suzuki reaction is as follows: arylhalide (0.5mmol) was weighed in 25mL round bottom flask containing boronic acids (0.6mmol), and Pd(OAc)2(PPh3)2/MgCe-HDC (100mg). The reactants and catalyst were dispersed in water (4mL), the RB was mounted on an oil bath at 353K and the mixture was stirred for 2h. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the catalyst was separated by filtration. Then the solution was extracted with ethyl acetate and brine solution. The organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by column chromatography on silicagel to afford pure product. The pure product was analyzed using 1H- and 13C-NMR techniques and compared with literature NMR data. |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In ethanol; water; toluene; at 100℃; for 16h; | To a 100mL round bottom flask equipped with a magnetic stir bar, o-tolylboronic acid (15mmol, 1.5equiv), K2CO3 (5.520g, 40mmol, 4.0equiv), and Pd(PPh3)4 (1154mg, 1.000mmol, 0.1equiv) were dissolved in 45mL toluene followed by the addition of 9mL of H2O and 15mL of EtOH. Then 2-bromoaniline (10mmol, 1.0equiv) was added and the resulting mixture was stirred at 100C for 16h. After cooling to room temperature, the biphasic solution was diluted with 50mL of saturated aqueous NH4Cl, and 30mL of CH2Cl2. The aqueous phase was extracted with diethyl ether (3×30mL) and the combined organic layers were washed with brine (40mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as eluent to afford the corresponding 2?-methylbiphenyl-2-amine (1p). 1H NMR (400MHz, CDCl3, TMS) delta 7.16-7.28 (m, 5H), 7.01 (d, J=7.2Hz, 1H), 6.80 (t, J=7.4Hz, 1H), 6.76 (d, J=7.6Hz, 1H), 3.44 (br s, 2H), 2.17 (s, 3H); 13C NMR (100MHz, CDCl3, TMS) delta 143.5, 138.6, 136.9, 130.2, 130.0, 130.0, 128.3, 127.7, 127.4, 126.1, 118.2, 115.0, 19.6. | |
With palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 6h; | General procedure: Reagents and conditions: (i) Pd(OAc)2, PCy3, Toluene, 0, 100C, 6h; (general yields 10-40%) | |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃; for 6h;Inert atmosphere; Schlenk technique; | General procedure: Taking 1d as an example: (A) Under a nitrogen atmosphere, a 100 mL Schlenk flask was charged with 2-bromoaniline (0.86 g, 5.0 mmol), 4-tert-butylphenylboronic acid (1.07 g, 6.0 mmol), Na2CO3 (1.33 g, 12.5 mmol), and a solvent mixture of toluene/EtOH/H2O (24 mL, 1:1:1 (v/v/v)) with stirring. Pd(PPh3)4 (0.29 g, 0.25 mmol) was added. Then, the mixture was stirred at 80 C for 6 h, cooled to room temperature, quenched with saturated NH4Cl, and extracted with EtOAc (3 × 25 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate (10:1 (v/v)) as eluents to afford 4'-(tert-butyl)-[1,1'-biphenyl]-2-amine as a yellow oil (0.88 g, 78%). |
Tags: 1203-41-4 synthesis path| 1203-41-4 SDS| 1203-41-4 COA| 1203-41-4 purity| 1203-41-4 application| 1203-41-4 NMR| 1203-41-4 COA| 1203-41-4 structure
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