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[ CAS No. 776239-07-7 ] {[proInfo.proName]}

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Chemical Structure| 776239-07-7
Chemical Structure| 776239-07-7
Structure of 776239-07-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 776239-07-7 ]

CAS No. :776239-07-7 MDL No. :MFCD12025320
Formula : C6H6BrFN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 205.03 Pubchem ID :-
Synonyms :

Safety of [ 776239-07-7 ]

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

Application In Synthesis of [ 776239-07-7 ]

* 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 [ 776239-07-7 ]

[ 776239-07-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 776239-07-7 ]
  • [ 298-12-4 ]
  • 2-(2-(2-bromo-5-fluorophenyl)hydrazono)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In water at 20℃; for 2h; To a solution of (2-bromo-5-fluorophenyl)hydrazine (2.15 g, 10.5 mmol) and concentrated HCl (1.2 mL) in water (30 mL) was added glyoxylic acid hydrate (1.06 g, 11.5 mmol). The resulting mixture was stirred at room temperature for 2 h. The precipitate that formed was collected by filtration, washed with water and dried at reduced pressure to afford the title compound as a yellow solid (2.67 g, 98% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 12.57 (1 H, s), 10.65 (1 H, s), 7.65 (1 H, s), 7.56 (1 H, dd, J=8.7, 5.9 Hz), 7.31 (1 H, dd, J=11.4, 3.0 Hz), 6.73 (1 H, td, J=8.5, 3.0 Hz); LCMS (+ESI, M+H+) m/z 261-263.
  • 2
  • [ 60481-35-8 ]
  • [ 776239-07-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; water;pH > 7; To a suspension of <strong>[60481-35-8](2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride</strong> (41 g, 0.17 mol; prepared from 2-bromo-5-fluoroaniline by the method described in U.S. Pat. No. 3,959,309 (1976) p-23, and p-48) in water (300 mL) and CH2Cl2 (200 mL) was added 1N-NaOH (200 mL) until the solution was basic. The CH2Cl2 layer was separated and the aqueous portion was further extracted with CH2Cl2 (150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to obtain 33 g (0.16 mol) of the title compound as an off-white powder: HPLC: 0.89 min (AP 97% at 220 nm); 1H NMR (CDCl3, 500 MHz) delta ppm 3.62 (2H, s, NH2), 5.75 (1H, s, NH), 6.37 (1H, m, 5-CH), 6.87 (1H, dd, J=11, 3 Hz, 3-CH), 7.31 (1H, dd, J=8.6, 5.8 Hz, 6-CH); 13C NMR (CDCl3, 125.8 Hz) 8ppm 100.0 (d, J=29 Hz, 3-CH), 101.4 (d, J=2.9 Hz, 1-C), 106.1 (d, J=23 Hz, 5-CH), 133.1 (d, J=9.6 Hz, 6-CH), 149.1 (d, J=10.6 Hz, 2-C), 163.5 (d, J=244 Hz, 4-CF); LC/MS m/z 205/207 (M+H).
  • 3
  • [ 1003-99-2 ]
  • [ 776239-07-7 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 2-bromo-5-fluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With tin(II) chloride dihdyrate In water at 0 - 20℃; for 5h;
Stage #1: 2-bromo-5-fluoroaniline With hydrogenchloride In water for 0.333333h; Cooling with ice; Stage #2: With sodium nitrite In water Stage #3: With sodium dihydrogenphosphate; sodium hydroxide; sodium sulfite In water at 75℃; for 1h; Cooling with ice; 14 Example 14; 4,4'-[4-fluoro-2-methyl-7-({4-[4-(pentafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic Acid By the same procedure as in Example 1→Example 2→Example 3→Example 4→Example 8→Example 9 using (2-bromo-5-fluorophenyl)hydrazine (which was prepared according to the following procedure: 2-bromo-5-fluoroaniline (20 g) was poured into 5N hydrochloric acid (200 mL) under ice-cooling, followed by stirring for 20 minutes, and a solution of sodium nitrite (8.0 g) in water (20 mL) was slowly added thereto, followed by stirring for 40 minutes. The reaction mixture and a 5N aqueous sodium hydroxide solution (150 mL) were added under ice-cooling to an aqueous solution (200 mL) of sodium sulfite (33 g) and sodium dihydrogen phosphate (1.7 g) with maintaining a pH of 6 or higher, followed by stirring at 75° C. for 1 hour. The reaction mixture was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was poured into concentrated hydrochloric acid at 60° C., followed by stirring for 2 hours, and at room temperature overnight. The reaction mixture was neutralized under ice-cooling with an aqueous 12N sodium hydroxide solution. The precipitated solid was filtered; washed with water; and dissolved in ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain a hydrazine compound.) instead of (2-bromophenyl)hydrazine hydrochloride, the compound of the present invention having the following physical properties was obtained.TLC:Rf 0.43 (methylene chloride:methanol=9:1)1H-NMR (DMSO-D6): δ 1.64-1.84, 1.88-2.02, 2.14-2.23, 2.33, 2.68-2.82, 4.02, 4.49-4.59, 6.76, 6.97, 7.19, 7.47, 12.08
Stage #1: 2-bromo-5-fluoroaniline With hydrogenchloride; sodium nitrite In water for 0.666667h; Cooling with ice; Stage #2: With sodium dihydrogenphosphate; sodium hydroxide; sodium sulfite In water at 75℃; for 1h; Cooling with ice; Stage #3: With hydrogenchloride In water at 60℃; for 2h; 10 Example 10 4,4'-[4-fluoro-2-methyl-7-({4-[4-(pentafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid (2-bromo-5-fluorophenyl)hydrazine was produced according to the following production method:2-bromo-5-fluoroaniline (20 g) was poured into 5N hydrochloric acid (200 mL) under ice-cooling, followed by stirring for 20 minutes, and a solution of sodium nitrite (8.0 g) in water (20 mL) was slowly added thereto, followed by stirring for 40 minutes. The reaction mixture and a 5N aqueous sodium hydroxide solution (150 mL) were added under ice-cooling to an aqueous solution (200 mL) of sodium sulfite (33 g) and sodium dihydrogen phosphate (1.7 g) with maintaining a pH of 6 or higher, followed by stirring at 75° C. for 1 hour. The reaction mixture was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was poured into concentrated hydrochloric acid at 60° C., followed by stirring for 2 hours, and at room temperature overnight. The reaction mixture was neutralized under ice-cooling with an aqueous 12N sodium hydroxide solution. The precipitated solid was filtered; washed with water; and dissolved in ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain a hydrazine compound.
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