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Chemical Structure| 15216-81-6 Chemical Structure| 15216-81-6

Structure of 15216-81-6

Chemical Structure| 15216-81-6

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Product Details of [ 15216-81-6 ]

CAS No. :15216-81-6
Formula : C7H4Cl2O2
M.W : 191.01
SMILES Code : O=C(Cl)C1=CC(Cl)=CC=C1O
MDL No. :MFCD11169665

Safety of [ 15216-81-6 ]

Application In Synthesis of [ 15216-81-6 ]

* 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 [ 15216-81-6 ]

[ 15216-81-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 15216-81-6 ]
  • [ 112734-22-2 ]
  • [ 314297-95-5 ]
YieldReaction ConditionsOperation in experiment
53% With triethylamine; In n-heptane; dichloromethane; ethyl acetate; A solution of 5-chloro-2-hydroxy-benzoyl chloride (4.00 g, 23.2 mmol) in dichloromethane (46 mL, 0.5 M) was treated with triethylamine (6.46 mL, 46.4 mmol) and <strong>[112734-22-2]4-bromo-2-fluorobenzylamine</strong> (6.10 g, 30.1 mmol). After stirring at room temperature for 16 h, the solution was washed successively with 2 N HCl and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. Purification by MPLC (10-50percent ethyl acetate in heptane, 23 mL/min, 70 min) gave N-(4-bromo-2-fluoro-benzyl)-4-chloro-2-hydroxy-benzamide as a white crystalline solid (4.4 g, 53percent): mp 159-161° C.; Rf 0.49 (30percent ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) delta 12.56 (br s, 1H), 9.28 (br t, J=5.4 Hz, 1H), 7.88 (d, J=6.0 Hz, 1H), 7.50 (dd, J1=9.9 Hz, J2=1.8 Hz, 1H), 7.37 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.33 (dd, J1=15.9 Hz, J2=8.1 Hz, 1H), 6.99-6.93 (m, 2H), 4.50-4.46 (m, 2H). ESI-LC/MS m/z calcd for C14H10BrClFNO2: 358.6; found 360.0 (M+1)+. Anal. calcd for C14H10BrClFNO2: C, 46.89; H, 2.81; N, 3.91; Cl, 19.78. Found C, 46.89; H, 2.81; N, 3.90; Cl, 19.73.
  • 2
  • [ 1123-93-9 ]
  • [ 15216-81-6 ]
  • N-(benzo[d]thiazol-5-yl)-5-chloro-2-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene; at 135℃; for 2h; [0136] 5-Chlorosalicyclic acid (215.7 mg, 1.250 mmol) was dissolved in TIIF (8.0 mL), followed by the addition of catalytic amount of DMF (10 .iL) and oxalyl chloride (0.13 mL, 1.500 mmol) respectively. The reaction was allowed to stir at rt for 30 mm and then concentrated in vacuo. The residue was re-dissolved in o-xylene followed by addition of benzo[d]thiazol-5- amine (150.2 mg, 1.000 mmol). The mixture was then heated to 135 °C and stirred at this temperature for 2 hours before it was cooled to rt and filtered. The filter cake was washed with cold diethyl ether to give N-(benzo[d]thiazol-5-yl)-5-chloro-2-hydroxybenzamide 15 as an off- white solid (40.6 mg, 13percent yield). ?H NMR (300 MHz, DMSO-d6) 6 11.10 (brs, 1H), 69.41 (d, J = 0.8 Hz, 1H), 8.59 (d, J= 2.0 Hz, 1H), 8.14 (dd, J= 8.7, 0.9 Hz, 1H), 7.95 (dd, J= 2.7, 0.9 Hz, 1H), 7.73 (dd, J= 8.7, 2.1 Hz, 1H), 7.44 (ddd, J= 8.9, 2.7, 0.9 Hz, 1H), 7.00 (dd, J 8.7, 0.9 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C14H1OC1N2O2S) requires m/z 305.0, found m/z 305.1.
  • 3
  • [ 15216-81-6 ]
  • [ 64628-73-5 ]
  • 5-chloro-N-[3-chloro-4-(trifluoromethoxy)phenyl]-2-hydroxy-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 25℃;Inert atmosphere; General procedure: A dry, 50 mL round bottom flask was charged with a magnetic stir bar then sealed with a septum and flushed with nitrogen. To this was added the salicylic acid derivative (2.0 mmol) and dichloromethane (10 mL). While stirring, SOCl2 (10 mmol) was added dropwise, followed by dimethylformamide (0.05 mmol), and the mixture was allowed to stir at room temperature under nitrogen for 12 hours. At this point, the mixture was concentrated under vacuum to afford the solid acid chloride derivative which was used immediately without further purification. The flask containing the acid chloride was then re-sealed with a septum and placed under a nitrogen atmosphere, and its contents were re-suspended in fresh dichloromethane (20 mL). While stirring, the aniline derivative (4.0 mmol) was added and the resulting opaque mixture was stirred for an additional 18 h. At this point, the mixture was quenched with ice water (5 mL) and phases were separated using a separatory funnel. The aqueous layer was extracted twice with dichloromethane (20 mL) then the organic layers were combined and washed with brine (40 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated under vacuum to afford a crude solid residue. This residue was then re-suspended in dichloromethane (10 mL) and adsorbed onto silica gel (1 g), then chromatographed on a 12 g silica gel column using a solvent gradient of 0-40% ethyl acetate in hexanes over 25 min. The product-containing fractions were combined then concentrated under vacuum to afford the purified salicylamide derivative.
  • 4
  • [ 15216-81-6 ]
  • [ 445-13-6 ]
  • 5-chloro-N-[3-chloro-4-(trifluoromethyl)phenyl]-2-hydroxy-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 25℃;Inert atmosphere; General procedure: A dry, 50 mL round bottom flask was charged with a magnetic stir bar then sealed with a septum and flushed with nitrogen. To this was added the salicylic acid derivative (2.0 mmol) and dichloromethane (10 mL). While stirring, SOCl2 (10 mmol) was added dropwise, followed by dimethylformamide (0.05 mmol), and the mixture was allowed to stir at room temperature under nitrogen for 12 hours. At this point, the mixture was concentrated under vacuum to afford the solid acid chloride derivative which was used immediately without further purification. The flask containing the acid chloride was then re-sealed with a septum and placed under a nitrogen atmosphere, and its contents were re-suspended in fresh dichloromethane (20 mL). While stirring, the aniline derivative (4.0 mmol) was added and the resulting opaque mixture was stirred for an additional 18 h. At this point, the mixture was quenched with ice water (5 mL) and phases were separated using a separatory funnel. The aqueous layer was extracted twice with dichloromethane (20 mL) then the organic layers were combined and washed with brine (40 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated under vacuum to afford a crude solid residue. This residue was then re-suspended in dichloromethane (10 mL) and adsorbed onto silica gel (1 g), then chromatographed on a 12 g silica gel column using a solvent gradient of 0-40% ethyl acetate in hexanes over 25 min. The product-containing fractions were combined then concentrated under vacuum to afford the purified salicylamide derivative.
  • 5
  • [ 15216-81-6 ]
  • [ 33322-60-0 ]
  • C16H15ClN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 90℃; for 2h; General procedure: 5-chloro-2-hydroxybenzoyl chloride (0.166 g, 0.869 mmol) and 4-nitroaniline (.060 g, 0.434 mmol) were suspended in Pyridine (1.5 mL) and stirred at room temperature for 1h. After this time it was heated at 90 C for 2h. The reaction mixture was then cooled to room temperature, diluted with EtOAc (20 mL), washed with 10% CuSO4 solution (20 mL), washed with 1N HCl solution, separated from aqueous layer, dried and concentrated to give the crude product which was purified by reverse phase HPLC.
 

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