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[ CAS No. 583-05-1 ] {[proInfo.proName]}

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Chemical Structure| 583-05-1
Chemical Structure| 583-05-1
Structure of 583-05-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 583-05-1 ]

CAS No. :583-05-1 MDL No. :MFCD00092889
Formula : C11H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RBLXWIPBPPVLPU-UHFFFAOYSA-N
M.W : 176.21 Pubchem ID :136371
Synonyms :

Safety of [ 583-05-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 583-05-1 ]

* 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 [ 583-05-1 ]

[ 583-05-1 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 583-05-1 ]
  • [ 33282-25-6 ]
  • 2
  • [ 100-52-7 ]
  • [ 2543-57-9 ]
  • [ 583-05-1 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanide In N,N-dimethyl-formamide
  • 3
  • [ 78-94-4 ]
  • [ 2901-80-6 ]
  • [ 583-05-1 ]
  • 4
  • [ 530-48-3 ]
  • [ 14284-89-0 ]
  • [ 119-61-9 ]
  • [ 102860-77-5 ]
  • [ 133216-64-5 ]
  • [ 583-05-1 ]
  • 6
  • [ 7149-03-3 ]
  • [ 583-05-1 ]
  • 3-bromo-4-(2-methyl-5-phenyl-pyrrol-1-yl)-benzoic acid ethyl ester [ No CAS ]
  • 7
  • [ 583-05-1 ]
  • [ 764650-97-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / methanol / 12 h / 50 °C 2: 91 percent / CH2Cl2 / 13 h / 23 °C
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / methanol / 12 h / 50 °C 2: 1.22 g / CH2Cl2 / 13 h / 23 °C
  • 8
  • [ 617-27-6 ]
  • [ 583-05-1 ]
  • [ 1325726-72-4 ]
  • 9
  • [ 17609-47-1 ]
  • [ 583-05-1 ]
  • [ 1325726-76-8 ]
  • 10
  • [ 69320-88-3 ]
  • [ 583-05-1 ]
  • [ 1325726-74-6 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: tert-Butyl 2-aminopropanoate hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-phenylpentane-1,4-dione With iodine In tetrahydrofuran at 20℃; for 24h;
  • 11
  • [ 402-67-5 ]
  • [ 583-05-1 ]
  • [ 357988-78-4 ]
YieldReaction ConditionsOperation in experiment
86% With indium; acetic acid In toluene for 2h; Inert atmosphere; Reflux; 37 4.2.37. 1-(3-Fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole (39) General procedure: Nitrobenzene derivative (1.0mmol) was added to a mixture of indium powder (460mg, 4.0mmol), and acetic acid (0.572mL, 10mmol) in toluene (2mL), followed by the addition of 2,5-hexadione or 1-phenyl-1,4-pentanedione (1.0mmol) in toluene (3mL). The reaction mixture was stirred at 80°C for 2,5-hexadione (or reflux for 1-phenyl-1,4-pentadione) under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30mL), filtered through Celite, poured into 10% NaHCO3 (30mL), and then extracted with ethyl acetate (30mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with hexane for most derivatives or ethyl acetate/hexane (v/v=5:95) for benzonitrile derivatives through a neutral silica gel column to give the corresponding pyrroles. The structures of the pyrroles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. If it is an unknown compound, elemental analysis data were reported additionally.
  • 12
  • [ 612-24-8 ]
  • [ 583-05-1 ]
  • [ 1446490-77-2 ]
YieldReaction ConditionsOperation in experiment
60% With indium; acetic acid In toluene for 24h; Inert atmosphere; Reflux; 41 4.2.41. 2-(2-Methyl-5-phenyl-1H-pyrrol-1-yl)benzonitrile (43) General procedure: Nitrobenzene derivative (1.0mmol) was added to a mixture of indium powder (460mg, 4.0mmol), and acetic acid (0.572mL, 10mmol) in toluene (2mL), followed by the addition of 2,5-hexadione or 1-phenyl-1,4-pentanedione (1.0mmol) in toluene (3mL). The reaction mixture was stirred at 80°C for 2,5-hexadione (or reflux for 1-phenyl-1,4-pentadione) under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30mL), filtered through Celite, poured into 10% NaHCO3 (30mL), and then extracted with ethyl acetate (30mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with hexane for most derivatives or ethyl acetate/hexane (v/v=5:95) for benzonitrile derivatives through a neutral silica gel column to give the corresponding pyrroles. The structures of the pyrroles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. If it is an unknown compound, elemental analysis data were reported additionally.
  • 13
  • [ 34800-90-3 ]
  • [ 583-05-1 ]
  • N-(2-methyl-5-phenyl-1H-pyrrol-1-yl)-2-(naphthalen-1-yl)acetamide [ No CAS ]
  • 14
  • [ 369-35-7 ]
  • [ 583-05-1 ]
  • 1-(2-fluoro-4-nitrophenyl)-2-methyl-5-phenyl-1H-pyrrole [ No CAS ]
  • 15
  • [ 6358-64-1 ]
  • [ 583-05-1 ]
  • 1-(4-chloro-2,5-dimethoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aminosulfonic acid In water at 60℃; for 5h; Synthesis of 2-methyl-1,5-diphenyl-1H-pyrrole (4); Typical Procedure General procedure: Cu(OTf)2 (5 mol%), MnCl2*4H2O (5 mol%), DBU (1.5 equiv.) and aqueous TBHP (4 equiv., 70% in water) were sequentially added to a mixture of styrene (0.5 mmol, 1 equiv.) and acetone (3 mL). The reaction was heated at 60 °C for 20 h, then cooled to room temperature before aniline (0.5 mmol, 1 equiv.) and H2NSO3H (5 mol%) was added and the reaction mixture heated at 60 °C for 5 h. The organic phase was removed under reduced pressure and the crude product purified by silica gel column chromatography (EtOAc-hexanes, 20%) to afford 4a as a pale-yellow solid.
  • 16
  • [ 827-94-1 ]
  • [ 583-05-1 ]
  • 2,6-dibromo-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With indium; acetic acid In toluene for 8h; Inert atmosphere; Reflux; 2. General procedure for the indium-mediated reductive reaction of 2,6-disubstutited nitroanilines with 2,5-hexanedione or 1-phenyl-1,4-pentanedione to obtain 4-(1H-pyrrol-1-yl)aniline derivatives General procedure: To a mixture of the 2,6-dihalo-4-nitroaniline derivative (1.0 mmol) and indium powder (459 mg, 4.0 mmol) in toluene (2.5 mL) was added acetic acid (573 μL, 10 mmol) followed by the 1,4-diketone (2.0 mmol) in toluene (2.5 mL). The resulting mixture was stirred at 80 qC (2,5-hexanedione) or reflux (1-phenyl-1,4-pentanedione) under a nitrogen atmosphere. After the reaction was complete, the reaction mixture was diluted with EtOAc (30 mL) or CH 2 Cl 2 (30 mL) and filtered through a celite pad. The filtrate was poured onto a 10% aqueous solution of NaHCO 3 (30 mL), the layers separated, and the aqueous layer extracted with EtOAc (30 mL u 3) or CH2Cl2 (30 mL u 3). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The resulting residue was purified using flash column chromatography on neutral silica gel eluted with EtOAc/hexane (v/v = 5/95) to give the corresponding pyrrole product. The structures of the pyrrole products, which were mostly novel compounds, were characterized using 1 H NMR, 13 C NMR and FTIR spectroscopy, GC-MS, and HRMS.
  • 17
  • [ 455-58-3 ]
  • [ 583-05-1 ]
  • 2-bromo-6-fluoro-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)aniline [ No CAS ]
  • C28H22BrFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 82% 2: 11% With indium; acetic acid In toluene for 12h; Inert atmosphere; Reflux; 2. General procedure for the indium-mediated reductive reaction of 2,6-disubstutited nitroanilines with 2,5-hexanedione or 1-phenyl-1,4-pentanedione to obtain 4-(1H-pyrrol-1-yl)aniline derivatives General procedure: To a mixture of the 2,6-dihalo-4-nitroaniline derivative (1.0 mmol) and indium powder (459 mg, 4.0 mmol) in toluene (2.5 mL) was added acetic acid (573 μL, 10 mmol) followed by the 1,4-diketone (2.0 mmol) in toluene (2.5 mL). The resulting mixture was stirred at 80 qC (2,5-hexanedione) or reflux (1-phenyl-1,4-pentanedione) under a nitrogen atmosphere. After the reaction was complete, the reaction mixture was diluted with EtOAc (30 mL) or CH 2 Cl 2 (30 mL) and filtered through a celite pad. The filtrate was poured onto a 10% aqueous solution of NaHCO 3 (30 mL), the layers separated, and the aqueous layer extracted with EtOAc (30 mL u 3) or CH2Cl2 (30 mL u 3). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The resulting residue was purified using flash column chromatography on neutral silica gel eluted with EtOAc/hexane (v/v = 5/95) to give the corresponding pyrrole product. The structures of the pyrrole products, which were mostly novel compounds, were characterized using 1 H NMR, 13 C NMR and FTIR spectroscopy, GC-MS, and HRMS.
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