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Chemistry
Organic Building Blocks
Triazoles
bromophenyl
MetAP2-IN-1
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Aryls Bromides Benzene Compounds
bromophenyl

[ CAS No. 5301-98-4 ] {[proInfo.proName]}

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Chemical Structure| 5301-98-4
Chemical Structure| 5301-98-4
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Product Details of [ 5301-98-4 ]

CAS No. :5301-98-4 MDL No. :
Formula : C8H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :RYKZCPFWGNDOQV-UHFFFAOYSA-N
M.W : 224.06 Pubchem ID :6419341
Synonyms :
Chemical Name :4-(4-Bromophenyl)-1H-1,2,3-triazole

Safety of [ 5301-98-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5301-98-4 ]

* 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 [ 5301-98-4 ]

[ 5301-98-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 136350-66-8 ]
  • [ 5301-98-4 ]
YieldReaction ConditionsOperation in experiment
65% With copper(l) iodide; sodium azide; potassium carbonate; sodium L-ascorbate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
Reference： [1]Location in patent: experimental part Wang, Xiaokun; Kuang, Chunxiang; Yang, Qing [European Journal of Organic Chemistry, 2012, # 2, p. 424 - 428]
  • 2
  • [ 32315-10-9 ]
  • [ 3466-80-6 ]
  • [ 5301-98-4 ]
  • [ 1402612-57-0 ]
YieldReaction ConditionsOperation in experiment
42% A solution of 2-benzyl piperidine (0.42 g, 2.6 mmol) in THF (8 mL) was treated with iPr2NEt (1.4 mL, 7.8 mmol) and triphosgene (0.39 g, 1.3 mmol), and the reaction mixture was stirred for 30 min at 4 C. The mixture was poured into H20 and extracted ethyl acetate. The organic layer was washed with H20 and brine, dried over Na2S04 and concentrated under reduced pressure. The intermediate was dissolved in THF (10 mL), and iPr2NEt (1.4 mL, 7.8 mmol), DMAP (0.32 g, 2.6 mmol) and 4-(4-bromophenyl)-lH-l,2,3-triazole (0.60 g, 2.6 mmol) were added to the solution. The mixture was stirred for 2h at 60 C and poured into saturated aqueous NH4C1 solution. The mixture was extracted with ethyl acetate, washed with H20 and brine, dried over Na2S04 and concentrated under reduced pressure. Chromatography (60 g; ethyl acetate :hexane= 1 :6) afforded 1,4-triazole urea KT179 (450 mg, 42%) as a top spot. 1HNMR (CDCI3, 400 MHz) delta = 8.40 (s, 1H), 7.75 (d, 2H, J = 8.5 Hz), 7.58 (d, 2H, J = 8.5 Hz), 7.43-7.26 (m, 5H), 5.91 (br, 1H), 4.36 (brd, 1H, J = 13.6 Hz), 3.18 (m, 1H), 2.52 (brd, 1H, J = 14.2 Hz), 2.15 (m, 1H), 1.90-1.60 (m, 4H). 13C NMR (CDC13, 150 MHz) delta = 150.15, 146.74, 138.66, 133.03, 129.85, 129.41, 128.27, 128.08, 127.42, 123.55, 122.01, 28.68, 26.67, 20.16. HRMS calculated for C20H2oBrN40 [M+H]+411.0815, found 411.0802.
Reference： [1]Patent: WO2012/138877,2012,A1 .Location in patent: Page/Page column 79
  • 3
  • [ 766-96-1 ]
  • [ 5301-98-4 ]
YieldReaction ConditionsOperation in experiment
74% With copper(l) iodide; sodium azide; acetic acid; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In N,N-dimethyl-formamide at 40℃; for 24h;
63% With copper(l) iodide; trimethylsilylazide In methanol; N,N-dimethyl-formamide at 100℃; for 12h; Sealed tube; Inert atmosphere; 6.1 Step 1: Synthesis of compound 4-(4-bromophenyl)-1H-1,2,3-triazole p-Bromophenyl acetylene (815 mg, 4.50 mmol) and cuprous iodide (44 mg, 0.23 mmol) were weighed and placed in a seal tube, to which was add 9 mL of a mixed solution of DMF and methanol (9:1), and the mixture was stirred well at room temperature. Then, trimethylsilyl azide (778 mg, 6.75 mmol) was added to the system. After that, the system was evacuated, and then argon was purged, that was repeated 5 times to ensure an inert gas atmosphere in the system. Then, the system was transferred to an oil bath at 100 °C, and the reaction was stirred under heating. After 12 h, the reaction was completed by TLC detection. After cooling to room temperature, the system was transferred to a round-bottom flask containing ethyl acetate (30 mL) and water (15 mL), stirred vigorously, and then allowed to stand for separation of layers. The aqueous phase was extracted with ethyl acetate (10 mL 3), and the organic phases were combined, successively washed with water (10 mL 3) and saturated brine (15 mL), dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation to obtain the crude product, which was separated and purified by column chromatography, to provide the compound 4-(4-bromophenyl)-1H-1,2,3-triazole (631 mg), with a yield of 63%. LC/MS (ESI+) calcd for C8H6BrN3+ (M + H+) m/z, 224.1; found, 224.0.
With copper(ll) sulfate pentahydrate; trimethylsilylazide; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 100℃; for 48h; 1 l-Bromo-4-ethynylbenzene (650 mg, 3.59 mmol) and trimethylsilyl azide (3.57 mL, 26.9 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL). CuSO4-5H2O (90 mg, 0.36 mmol) in water (1.0 mL) and sodium ascorbate (285 mg, 1.44 mmol) in water (1.0 mL) were added, and the sealed reaction mixture was stirred at 100°C for 48 h. The mixture was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (dry load, 0-50% EtOAc/hexanes) afforded the title compound as a colorless solid. Calc'd for C8H7BrN3 [M+H]+ 224, found 224.
Multi-step reaction with 2 steps 1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol / 12 h 2: copper diacetate; oxygen; pyridine / 5 h / 80 °C / Green chemistry
With copper(l) iodide; trimethylsilylazide In methanol; N,N-dimethyl-formamide at 100℃; for 17h; Schlenk technique; Inert atmosphere;
Multi-step reaction with 2 steps 1: copper(I) thiophene-2-carboxylate hydrate / toluene / 24 h / 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere
With trimethylsilylazide 6.1 Step 1: Step 1: Synthesis of compound 4-(4-bromophenyl)-1H-1,2,3-triazole p-Bromophenyl acetylene (815 mg, 4.50 mmol) and cuprous iodide (44 mg, 0.23 mmol) were weighed and placed in a seal tube, to which was add 9 mL of a mixed solution of DMF and methanol (9:1), and the mixture was stirred well at room temperature. Then, trimethylsilyl azide (778 mg, 6.75 mmol) was added to the system. After that, the system was evacuated, and then argon was purged, that was repeated 5 times to ensure an inert gas atmosphere in the system. Then, the system was transferred to an oil bath at 100 °C, and the reaction was stirred under heating. After 12 h, the reaction was completed by TLC detection. After cooling to room temperature, the system was transferred to a round-bottom flask containing ethyl acetate (30 mL) and water (15 mL), stirred vigorously, and then allowed to stand for separation of layers. The aqueous phase was extracted with ethyl acetate (10 mL∗3), and the organic phases were combined, successively washed with water (10 mL∗3) and saturated brine (15 mL), dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation to obtain the crude product, which was separated and purified by column chromatography, to provide the compound 4-(4-bromophenyl)-1H-1,2,3-triazole (631 mg), with a yield of 63%. LC/MS (ESI+) calcd for C8H6BrN3+ (M + H+) m/z, 224.1; found, 224.0.

Reference： [1]Jankovič, Dominik; Virant, Miha; Gazvoda, Martin [Journal of Organic Chemistry, 2022, vol. 87, # 6, p. 4018 - 4028]
[2]Current Patent Assignee: HINOVA PHARMACEUTICALS - EP3950678, 2022, A1 Location in patent: Paragraph 0049-0050
[3]Current Patent Assignee: MERCK & CO INC - WO2008/156726, 2008, A1 Location in patent: Page/Page column 106
[4]Cha, Hyojin; Lee, Kyongkyu; Chi, Dae Yoon [Tetrahedron, 2017, vol. 73, # 20, p. 2878 - 2885]
[5]Chao, Zengyin; Ma, Mingming; Gu, Zhenhua [Organic Letters, 2020, vol. 22, # 16, p. 6441 - 6446]
[6]Wang, Tao; Tang, Zongyuan; Luo, Han; Tian, Yi; Xu, Mingchuan; Lu, Qixing; Li, Baosheng [Organic Letters, 2021, vol. 23, # 16, p. 6293 - 6298]
[7]Current Patent Assignee: HINOVA PHARMACEUTICALS - EP3950678, 2022, A1
  • 4
  • [ 75-52-5 ]
  • [ 873-75-6 ]
  • [ 5301-98-4 ]
YieldReaction ConditionsOperation in experiment
90% With sodium azide; dihydrogen peroxide In ethanol at 78℃; 2.3 General Procedure for Synthesis of 4-aryl-NH-1, 2, 3-triazoles General procedure: A round-bottomed flask (10 mL) was charged with benzyl alcohol (1.0 mmol), sodium azide (2.0 mmol), H2O2(3 mmol) and nitromethane (2.0 mmol) were added in ethanol (4 mL). Afterwards, the mixture was refluxed in the presence of 40 mg Fe3O4SiO2TCT-DABCO-SO3H magnetic catalyst. After completion of the reaction, the magnetic catalyst was separated by using an external magnet, finally, the product had to be isolated by column chromatography on silica gel (70-230 Mesh) using n-hexane-ethyl (4:1) acetate as eluent.
Reference： [1]Bagheri, Sepideh; Heydari, Akbar; Jadidi Nejad, Masoumeh; Pazoki, Farzane; Yazdani, Elahe [Journal of Chemical Sciences, 2020, vol. 132, # 1]

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