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Chemical Structure| 91167-74-7 Chemical Structure| 91167-74-7

Structure of 91167-74-7

Chemical Structure| 91167-74-7

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Product Details of [ 91167-74-7 ]

CAS No. :91167-74-7
Formula : C6H6ClFN2O
M.W : 176.58
SMILES Code : OC1=CC(NN)=C(F)C=C1Cl

Safety of [ 91167-74-7 ]

Application In Synthesis of [ 91167-74-7 ]

* 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 [ 91167-74-7 ]

[ 91167-74-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 84478-72-8 ]
  • [ 91167-74-7 ]
YieldReaction ConditionsOperation in experiment
With stannous chloride; urea; sodium nitrite; In hydrogenchloride; sodium hydroxide; water; EXAMPLE 6 Production of the substituted phenylhydrazine (IV): <strong>[84478-72-8]4-Chloro-2-fluoro-5-hydroxyaniline</strong> (10 g) was dissolved in conc. hydrochloric acid (130 ml) under heating, and the resultant mixture was cooled to 0 C. To the resulting mixture, there was dropwise added a solution of sodium nitrite (4.5 g) in water (20 ml). After completion of the addition, the mixture was further stirred at 5 to -5 C. for 1 hour, and urea was added thereto, whereby excessive sodium nitrite ion was decomposed. The resulting mixture was cooled to -30 to -25 C., and a solution of anhydrous stannous chloride (20.5 g) in conc. hydrochloric acid (40 ml) was added thereto, followed by stirring at -10 to 0 C. for 3 hours. The precipitated crystals were collected by filtration, washed with a small amount of water and dissolved in a 10% aqueous sodium hydroxide solution. The resultant solution was adjusted to pH 7 and extracted with ethyl acetate. The extract was dried and concentrated. The crystallized residue was washed with ether to obtain 1 g of 4-chloro-2-fluoro-5-hydroxyphenylhydrazine. m.p., 149-150 C. (decomp.).
With stannous chloride; urea; sodium nitrite; In hydrogenchloride; sodium hydroxide; water; EXAMPLE 8 Production of the substituted phenylhydrazine (VII): <strong>[84478-72-8]4-Chloro-2-fluoro-5-hydroxyaniline</strong> (10 g) was dissolved in conc. hydrochloric acid (130 ml) under heating, and the resultant mixture was cooled to 0 C. To the resulting mixture, there was dropwise added a solution of sodium nitrite (4.5 g) in water (20 ml). After completion of the addition, the mixture was further stirred at 5 to -5 C. for 1 hour, and urea was added thereto, whereby excessive sodium nitrite ion was decomposed. The resulting mixture was cooled to -30 to -25 C., and a solution of anhydrous stannous chloride (20.5 g) in conc. hydrochloric acid (40 ml) was added thereto, followed by stirring at -10 to 0 C. for 3 hours. The precipitated crystals were collected by filtration, washed with a small amount of water and dissolved in a 10% aqueous sodium hydroxide solution. The resultant solution was adjusted to pH 7 and extracted with ethyl acetate. The extract was dried and concentrated. The crystallized residue was washed with ether to obtain 1 g of 4-chloro-2-fluoro-5-hydroxyphenylhydrazine. m.p., 149-150 C. (decomp.).
  • 2
  • nitrite ion [ No CAS ]
  • [ 84478-72-8 ]
  • [ 91167-74-7 ]
YieldReaction ConditionsOperation in experiment
With stannous chloride; urea; sodium nitrite; In hydrogenchloride; water; EXAMPLE 4 <strong>[84478-72-8]4-Chloro-2-fluoro-5-hydroxyaniline</strong> (32.5 g) was added to conc. hydrochloric acid (300 ml), and a solution of sodium nitrite (15.2 g) in water (20 ml) was added thereto at 0 to -5 C. The resultant mixture was stirred at 0 to 5 C. for 30 minutes, and urea was added thereto to rremove excessive nitrite ion, followed by cooling to -30 C. A solution of stannous chloride (92 g) in hydrochloric acid (160 ml) was added thereto, and the mixture was stirred at 0 to -10 C. for 3 hours. The reaction mixture was filtered, and the precipitated crystals were dissolved in water, neutralized with sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was treated with ether to give 4-chloro-2-fluoro-5-hydroxyphenylhydrazine (8.4 g) as crystals.
 

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