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Chemistry
Heterocyclic Building Blocks
Imidazolines
2-(4-Bromophenyl)-4,5-dihydro-1H-imidazole
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Imidazolines
Aryls Bromides

[ CAS No. 206535-83-3 ] {[proInfo.proName]}

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Chemical Structure| 206535-83-3
Chemical Structure| 206535-83-3
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CAS No. :206535-83-3 MDL No. :MFCD07776868
Formula : C9H9BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 225.09 Pubchem ID :-
Synonyms :

Safety of [ 206535-83-3 ]

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Application In Synthesis of [ 206535-83-3 ]

* 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 [ 206535-83-3 ]

[ 206535-83-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 206535-83-3 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
83% With [bis(acetoxy)iodo]benzene; potassium carbonate In dimethyl sulfoxide at 20℃; for 24h;
78% With oxygen; pyrographite In xylene at 120℃; for 25h;
Reference： [1]Ishihara, Midori; Togo, Hideo [Synlett, 2006, # 2, p. 227 - 230]
[2]Haneda, Satoshi; Okui, Ayaka; Ueba, Chigusa; Hayashi, Masahiko [Tetrahedron, 2007, vol. 63, # 11, p. 2414 - 2417]
  • 2
  • [ 623-00-7 ]
  • [ 107-15-3 ]
  • [ 206535-83-3 ]
YieldReaction ConditionsOperation in experiment
93% With [Ru(CO)(pyridoxalthiosemicarbazone hydrochloride)(triphenylphosphine)2] In neat (no solvent) at 80℃; for 3h; 3 2-(4-Chloro-phenyl)-4,5-dihydro-1H-imidazole General procedure: A mixture of nitrile (1.0 mmol), ethylenediamine (2.0 mmol) and catalyst (4 mol%) were heated under solvent-free conditions with stirring at 80°C. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography to provide the desired product. The products were characterized by elemental analyses, 1H NMR [49],31C NMR and ESI-MS spectra. 2.6.3 ;2-(4-bromo-phenyl)-4,5-dihydro-1H-imidazole; Anal. Calc. for C9H9BrN2 (225.09 g, mol-1): C, 48.02; H, 4.03; N, 145%. Found: C, 48.34; H, 4.41; N, 164%. 1H NMR (DMSO-d6, δ): 7.43-7.48 (d, 2H, aromatic CH), 7.22-7.24 (d, 2H, aromatic CH), 4.26 (s, 1H, NH), 3.71-3.75 (t, 2H, CH2), 3.60-3.67 (t, 2H, CH2). ;13C NMR (DMSO-d6, δ): 164.5, 137.7, 134.7, 130, 130.6, 54.5, 36.1. ESI-MS, m/z: 224.0 [M]+.
93% With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 2.5h; chemoselective reaction;
85% With Cu(II) immobilized on Fe3O4-agarose nanomagnetic catalyst functionalized with ethanolamine phosphate-salicylaldehyde Schiff base at 100℃; for 1.5h; 3.6. Typical procedure for preparation of 2-phenyl-4,5-dihydro-1H-imidazole catalyzed in the presence of Fe3O4 Agarose/SAEPH2 /Cu(II) General procedure: A mixture of benzonitrile (0.1 g, 1 mmol), ethanediamine (0.09 g, 1.5 mmol), and Fe3O4 Agarose/SAEPH2 /Cu(II) nanomagnetic catalyst (0.05 g, 14 mol%) was stirred at 100 °C. The progress of the reaction was monitored by TLC. After completion of the reaction, the nanomagnetic catalyst was separated with an external magnetic field and the crude product was recrystallized from n-hexane to afford the pure 2-phenyl-4, 5-dihydro-1H-imidazole (0.13 g, 95%). The nanomagnetic catalyst was washed with hot ethyl acetate several times to remove unreacted starting materials and then was dried at 70 °C for 5 h and used in the next run.
54% With sodium carbonate In methanol at 80℃; for 15h; Inert atmosphere; Schlenk technique;

Reference： [1]Manikandan, Rajendran; Anitha, Panneerselvam; Prakash, Govindan; Vijayan, Paranthaman; Viswanathamurthi, Periasamy; Butcher, Ray Jay; Malecki, Jan Grzegorz [Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 312 - 324]
[2]Hojati, Seyedeh Fatemeh; Nezhadhoseiny, Seyede Atefe [Journal of the Serbian Chemical Society, 2012, vol. 77, # 9, p. 1181 - 1189,9]
[3]Zarei, Zeinab; Akhlaghinia, Batool [Turkish Journal of Chemistry, 2018, vol. 42, # 1, p. 170 - 191]
[4]Garg, Parul; Chaudhary, Shweta; Milton, Marilyn D. [Journal of Organic Chemistry, 2014, vol. 79, # 18, p. 8668 - 8677]

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