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[ CAS No. 39561-82-5 ] {[proInfo.proName]}

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Chemical Structure| 39561-82-5
Chemical Structure| 39561-82-5
Structure of 39561-82-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 39561-82-5 ]

CAS No. :39561-82-5 MDL No. :MFCD00662320
Formula : C10H9ClO3 Boiling Point : -
Linear Structure Formula :C10H9O3Cl InChI Key :-
M.W :212.63 Pubchem ID :-
Synonyms :

Safety of [ 39561-82-5 ]

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Application In Synthesis of [ 39561-82-5 ]

* 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 [ 39561-82-5 ]

[ 39561-82-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 25128-35-2 ]
  • [ 39561-82-5 ]
  • 2-(4-chloro-phenyl)-3-hydroxy-quinoline-4,8-dicarboxylic acid [ No CAS ]
  • 2
  • [ 127-09-3 ]
  • [ 536-38-9 ]
  • [ 39561-82-5 ]
YieldReaction ConditionsOperation in experiment
83% With acetic acid In ethanol; water for 2.5h; Heating;
83% With acetic acid In water at 20℃; Heating / reflux; 2 This compound was prepared as described by Cragoe et al. (J. Org. Chem., 1953, 18, 561), except that the phenacyl bromide was used instead of the phenacyl chloride. A suspension of 2-bromo-4'-chloroacetophenone (Aldrich, 50 g, 0.21 mol) in 220 mL ethanol was prepared in a 1 L round-bottomed flask, and a solution of sodium acetate trihydrate (32 g, 0.24 mol) in 110 mL water and 11 mL acetic acid was added. The mixture was heated at reflux for 2.5 hours, then cooled to room temperature and refrigerated overnight. The white crystalline material which precipitated was collected by filtration, washing once with a cold solution of 50% aqueous ethanol, and dried under vacuum to give pure phenacyl acetate 4 (38 g, 83% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.22 (s, 3H) 5.28 (s, 2H) 7.46 (d, J=8.59 Hz, 2H) 7.85 (d, J=8.59 Hz, 2H).
83% In ethanol; water; acetic acid for 2.5h; Heating / reflux; 2.4; 2 Compound 2 was prepared as described by Cragoe et al. (J. Org. Chem., 1953, 18, 561), except that the phenacyl bromide was used instead of the phenacyl chloride. A suspension of 2-bromo-4'-chloroacetophenone (Aldrich, 50 g, 0.21 mol) in 220 mL ethanol was prepared in a 1 L round-bottomed flask, and a solution of sodium acetate trihydrate (32 g, 0.24 mol) in 110 mL water and 11 mL acetic acid was added. The mixture was heated at reflux for 2.5 hours, then cooled to room temperature and refrigerated overnight. The white crystalline material which precipitated was collected by filtration, washing once with a cold solution of 50% aqueous ethanol, and dried under vacuum to give pure phenacyl acetate 4 (38 g, 83% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.22 (s, 3H) 5.28 (s, 2H) 7.46 (d, J=8.59 Hz, 2H) 7.85 (d, J=8.59 Hz, 2H).
With ethanol
With ethanol
In ethanol Reflux; α-hydroxy-4’-chloroacetophenone (3a) General procedure: α-bromo-3’-chloroacetophenone (6a, 17.5 g, 75 mM) in ethanol (100 mL) was refluxed for 10 h with anhydrous sodium acetate (6.2 g, 76 mM). The mixture was diluted with water and the solid which separated was collected and recrystallized from ethyl acetate. Then the solid (2-(3-chlorophenyl)-2-oxoethyl acetate, 10.4 g, 49 mM, 65%) in ethanol (50 mL) and hydrochloric acid (50 mL of 1 M) was refluxed for 6 h. The mixture was diluted with water and was then extracted with ethyl acetate. The extract was dried (sodium sulfate) and concentrated to give 2a (6.8 g, 40 mM, 53%).

  • 3
  • [ 111-75-1 ]
  • [ 39561-82-5 ]
  • [ 23972-47-6 ]
YieldReaction ConditionsOperation in experiment
52% With formic acid at 180℃; for 20h;
  • 4
  • [ 39561-82-5 ]
  • [ 1530-39-8 ]
  • (E)-2,3-bis(4-chlorophenyl)prop-2-en-1-yl acetate [ No CAS ]
  • (Z)-2,3-bis(4-chlorophenyl)prop-2-en-1-yl acetate [ No CAS ]
  • 5
  • [ 52351-75-4 ]
  • [ 39561-82-5 ]
  • C17H12ClNO4 [ No CAS ]
  • 6
  • [ 77395-10-9 ]
  • [ 39561-82-5 ]
  • C17H11BrClNO3 [ No CAS ]
  • 7
  • [ 109496-98-2 ]
  • [ 39561-82-5 ]
  • C22H14ClNO3 [ No CAS ]
  • 8
  • [ 1127-59-9 ]
  • [ 39561-82-5 ]
  • C17H12ClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: 7-methyl-1H-indole-2,3-dione With potassium hydroxide at 100℃; Stage #2: 4-chlorophenacyl acetate In ethanol; water for 5h; Heating; Further stages.;
  • 9
  • [ 150560-58-0 ]
  • [ 39561-82-5 ]
  • C19H16ClNO3 [ No CAS ]
  • 10
  • [ 149125-30-4 ]
  • [ 39561-82-5 ]
  • C17H9ClF3NO4 [ No CAS ]
  • 11
  • [ 39561-82-5 ]
  • [ 391-12-8 ]
  • C17H9ClF3NO3 [ No CAS ]
  • 12
  • [ 84575-27-9 ]
  • [ 39561-82-5 ]
  • C17H12ClNO4 [ No CAS ]
  • 13
  • [ 25128-32-9 ]
  • [ 39561-82-5 ]
  • C17H10ClNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 1H-indole-2,3-dione-5-carboxylic acid With potassium hydroxide at 100℃; Stage #2: 4-chlorophenacyl acetate In ethanol; water for 5h; Heating; Further stages.;
  • 14
  • [ 57817-00-2 ]
  • [ 39561-82-5 ]
  • C20H18ClNO3 [ No CAS ]
  • 15
  • [ 39561-82-5 ]
  • [ 4919-43-1 ]
  • C20H12ClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The procedure described above for the synthesis of Compound 2 was followed, reacting intermediate 5 (2.19 g, 11.1 mmol) with 4-chlorophenacyl acetate (intermediate 4, 2.95 g, 13.9 mmol). The crude acid was purified by flash chromatography over silica gel (70 ethyl acetate: 5 acetonitrile: 2.5 methanol: 2.5 water [+0.5% triethylamine]). The product was not pure enough and therefore purified again by Discovery Analytical Chemistry (preparative HPLC, acetonitrile/water/triethylamine). After lyophilization, product Compound 3 was obtained as the triethylammonium salt, a yellow solid (54 mg, 1.1% yield): 1H NMR (400 MHz, DMSO-D6) delta 1.17 (t, J=7.3 Hz, 9H) 3.09 (m, 6H) 7.57 (m, 3H) 7.65 (m, 1H) 7.80 (d, J=9.1 Hz, 1H) 7.89 (d, J=8.6 Hz, 1H) 8.55 (dt, J=9.1, 2.5, 2.3 Hz, 2H) 9.13 (d, J=8.8 Hz, 1H) 9.53 (d, J=9.4 Hz, 1H); HRMS (ESI+) calcd for C20H13ClNO3 350.0579, found 350.0580.
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