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[ CAS No. 446-09-3 ]

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Chemical Structure| 446-09-3
Chemical Structure| 446-09-3
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CAS No. :446-09-3 MDL No. :MFCD00055530
Formula : C6H3BrFNO2 Boiling Point : 220.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :220.00 g/mol Pubchem ID :2773383
Synonyms :

Safety of [ 446-09-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 446-09-3 ]

  • Upstream synthesis route of [ 446-09-3 ]
  • Downstream synthetic route of [ 446-09-3 ]

[ 446-09-3 ] Synthesis Path-Upstream   1~19

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  • [ 387-43-9 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
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  • [ 40311-13-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 44, p. 10511 - 10515
  • 3
  • [ 446-09-3 ]
  • [ 394-33-2 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 3, p. 473 - 476
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  • [ 460-00-4 ]
  • [ 364-73-8 ]
  • [ 446-09-3 ]
Reference: [1] Bl. Acad. Belg., vol. <5> 12, p. 804,815[2] Chem. Zentralbl., 1927, vol. 98, # I, p. 884
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Reference: [1] Bl. Acad. Belg., vol. <5> 12, p. 802[2] Chem. Zentralbl., 1927, vol. 98, # I, p. 884
  • 6
  • [ 394-01-4 ]
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YieldReaction ConditionsOperation in experiment
48% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium bromide In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,37 mg of 2-nitro-4-fluorobenzoic acid and 30.9 mg of sodium bromide4 mL of dimethyl sulfoxide. Heat 160 ° C in the presence of oxygenReaction for 24 hours. After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases were concentrated to give 21.1 mg of 2-nitro-4-fluorobromobenzene,The yield is 48percent.
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A, . Location in patent: Paragraph 0067
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
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Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
[2] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 17, p. 7912 - 7918
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 51, p. 12257 - 12261
[4] Patent: WO2009/153307, 2009, A1, . Location in patent: Page/Page column 53-54
[5] Patent: US2010/29729, 2010, A1, . Location in patent: Page/Page column 25
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  • [ 364-78-3 ]
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Reference: [1] Bl. Acad. Belg., vol. <5> 12, p. 804,815[2] Chem. Zentralbl., 1927, vol. 98, # I, p. 884
[3] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1976, vol. 30, p. 141 - 149
[4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5259 - 5272
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  • [ 460-00-4 ]
  • [ 364-73-8 ]
  • [ 446-09-3 ]
Reference: [1] Bl. Acad. Belg., vol. <5> 12, p. 804,815[2] Chem. Zentralbl., 1927, vol. 98, # I, p. 884
  • 10
  • [ 351-83-7 ]
  • [ 446-09-3 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1976, vol. 30, p. 141 - 149
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  • [ 448-39-5 ]
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1976, vol. 30, p. 141 - 149
  • 12
  • [ 7697-37-2 ]
  • [ 460-00-4 ]
  • [ 40466-95-3 ]
  • [ 364-73-8 ]
  • [ 446-09-3 ]
  • [ 586-78-7 ]
Reference: [1] Bl. Acad. Belg., vol. <5> 12, p. 802[2] Chem. Zentralbl., 1927, vol. 98, # I, p. 884
  • 13
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  • [ 1003-99-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With iron; acetic acid In ethanol at 20℃; for 2.08333 h; Heating / reflux
Stage #2: With sodium hydroxide In diethyl ether; water
2-Bromo-5-fluorobenzenamine; To a solution of 1-bromo-4-fluoro-2-nitrobenzene (5.0 g, 22.7 mmol) in HOAc/EtOH (20 mL/20 mL) was added iron powder in one portion at room temperature. The mixture was bubbled with N2 for 5 min, and then refluxed for 2 hrs. Partial of the solvents were removed on rotary vacuum, then the residue was partitioned between aqueous NaOH (10N, 200 mL) and Et2O (200mL). After separation, the organic phase was washed with H2O(50 mL), brine (50 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product, as an light tan oil (quantitative yield), which was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 4.15 (s, 1 H), 6.34 (td, J=8.44, 2.77 Hz, 1 H) ,6.46 (dd, J=10.20, 2.90 Hz, 1 H), 7.31 (dd, J=8.81, 5.79 Hz, 1 H); Mass spec. 189.94 (MH+), Calc. for C6H5BrFN 188.96.
Reference: [1] Patent: US2007/259850, 2007, A1, . Location in patent: Page/Page column 95-96
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 51, p. 12257 - 12261
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5259 - 5272
[4] Patent: US2006/94707, 2006, A1, . Location in patent: Page/Page column 61
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
[6] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137
  • 14
  • [ 446-09-3 ]
  • [ 73183-34-3 ]
  • [ 74386-13-3 ]
YieldReaction ConditionsOperation in experiment
60% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane for 3 h; Reflux Reaction 1-1 (19.48 g, 89 mmol) was added sequentially to a 1 L round bottom flask.Bis(pinacolato)diboron(27 g, 106 mmol), bis(triphenylphosphine)palladium dichloride (3.1 g, 4.45 mmol), potassium acetate (KOAc) (22 g, 222 mmol) and 1,4-Dioxane (445 mL) was stirred with stirring to reflux. After 3 hours, the mixture was extracted with methylene chloride and distilled water. After that, Intermediate 1-1 (13.08 g, 60percent) was obtained by column chromatography.
Reference: [1] Patent: CN108383842, 2018, A, . Location in patent: Paragraph 0056; 0057; 0059
  • 15
  • [ 446-09-3 ]
  • [ 1826-67-1 ]
  • [ 292636-09-0 ]
YieldReaction ConditionsOperation in experiment
47% at -45 - -40℃; for 0.5 h; Example S66; Preparation of 4-fluoro-1H-indole-7-carboxylic acid; 1.12 g (5 mmol) of 2-bromo-5-fluoro-nitrobenzene were dissolved in 50 ml THF. At a temperature of -45° C. 15 ml of a 1M vinyl magnesium bromide solution in THF were added under nitrogen in such a way that the temperature did not exceed -40° C. After complete addition the dark solution was stirred for 30 min at -40° C. The reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution and extracted twice with diethyl ether. The combined organic layers were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was dissolved in DCM and purified by column chromatography (100 g silica gel; heptane/EtOAc 9:1) to yield 501 mg (47percent) 7-bromo-4-fluoro-1H-indole as an orange oil. MS (EI) 213.0 (100), 215.0 (100) (M)+.
Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5856 - 5869
[3] Patent: US2006/30613, 2006, A1, . Location in patent: Page/Page column 35
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
[5] Patent: WO2009/153307, 2009, A1, . Location in patent: Page/Page column 54
[6] Patent: US2010/29729, 2010, A1, . Location in patent: Page/Page column 25
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  • [ 292636-09-0 ]
YieldReaction ConditionsOperation in experiment
57% With vinyl magnesium bromide In tetrahydrofuran; 1,2-dimethoxyethane at -78℃; for 4 h; Inert atmosphere Intermediate 120: 7-Bromo-4-fluoro-1 H-indole.A solution of 1-bromo-4-fluoro-2-nitrobenzene (3.6 g, 16.4 mmol) in THF (100 ml.) was added to a solution of 1 M vinylmagnesium bromide in THF (100 ml_, 100 mmol) and DME (100 ml.) at -78 0C (bath temp). The reaction was stirred at -78 0C for 4 h, and saturated aqueous NH4CI was added. The layers were separated, and the organic layer was evaporated. The crude product was purified flash chromatography, giving 2g (57percent) of the title compound.
Reference: [1] Patent: WO2008/118724, 2008, A1, . Location in patent: Page/Page column 131
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  • [ 292636-13-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
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  • [ 344790-96-1 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
  • 19
  • [ 446-09-3 ]
  • [ 313337-34-7 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
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