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[ CAS No. 89488-25-5 ]

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Chemical Structure| 89488-25-5
Chemical Structure| 89488-25-5
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Product Details of [ 89488-25-5 ]

CAS No. :89488-25-5 MDL No. :MFCD06659863
Formula : C6H6BClO3 Boiling Point : 369.275°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :172.37 g/mol Pubchem ID :-
Synonyms :

Safety of [ 89488-25-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89488-25-5 ]

  • Downstream synthetic route of [ 89488-25-5 ]

[ 89488-25-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 89466-08-0 ]
  • [ 89488-25-5 ]
YieldReaction ConditionsOperation in experiment
With chlorine In acetic acid
  • 2
  • [ 89488-25-5 ]
  • [ 78607-36-0 ]
  • [ 1018687-75-6 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In water; acetonitrile at 20 - 80℃; The title compound was prepared using methods analogous to those in Representative Procedure A. 1H NMR (500 MHz, CDCl3, δ): 8.41 (dd, J=4.8, 1.9 Hz, 1H), 7.73 (dd, J=7.5, 1.9 Hz, 1H), 7.35 (dd, J=7.5, 4.8 Hz, 1H), 7.29 (dd, J=8.7, 2.6 Hz, 1H), 7.19 (d, J=2.6 Hz, 1H), 6.95 (d, J=8.7 Hz, 1H), 6.05 (br s, 1H); 13C NMR (126 MHz, CDCl3, δ): 157.8, 150.7, 149.1, 140.9, 132.4, 130.4, 130.1, 125.8, 125.74, 122.6, 117.7; HRMS (ESI+): calculated for C11H8Cl2NO [M+H+], 239.9977; m/z found, 239.9976.
  • 3
  • [ 89488-25-5 ]
  • [ 703-61-7 ]
  • [ 956125-03-4 ]
YieldReaction ConditionsOperation in experiment
22% With sodium carbonate In water; toluene for 15h; Reflux; Inert atmosphere; 37 4-Chloro-2-(4-chloro-quinolin-2-yl)-phenol 2,4-Dichloroquinoline (0.29 g, 1.5 mmol), 2-hydroxy-5-chloro boronic acid (0.24 g, 1.44 mmol), sodium carbonate (0.31 g, 3 mmol) and palladium tetrakistriphenylphosphine (0.086 g, 0.075 mmol) were suspended in a previously degassed mixture of toluene (3 mL) and water (1 mL). The reaction mixture was refluxed under nitrogen for 15 hours and allowed to cool to room temperature. The contents of the flask were dissolved in ethyl acetate (100 mL) and water (100 mL) and the layers were separated. The aqueous layer was extracted with another portion of ethyl acetate (100 mL), the organics were combined, washed with water (100 mL) and brine (100 mL), dried with magnesium sulfate, filtered, and evaporated to give a pale red solid. The solid was triturated with ethyl acetate to give a yellow solid. Yield: 100 mg, 22%. Analytical LCMS method 2 retention time 7.91 min, M+H=290.
  • 4
  • [ 956124-96-2 ]
  • [ 89488-25-5 ]
  • [ 956124-97-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water; toluene; butan-1-ol for 48h; Heating; 27 {(R)-2-[2-(5-Chloro-2-hydroxy-phenyl)-pyrimidin-4-ylamino]-1-methyl-ethyl}-carbamic acid benzyl ester (5-Chloro-2-hydroxyphenyl)boronic acid (0.6 mmol, 0.1 g) and palladium tetrakistriphenylphosphine (0.01 mmol, 0.011 g) were weighed into a tube and placed under a nitrogen atmosphere. A previously de-gassed sodium carbonate solution (2 M, 1 mL) was added. (R)-2-(2-Chloro-pyrimidin-4-ylamino)-1-methyl-ethyl]-carbamic acid benzyl ester (0.2 mmol, 0.06 g) was dissolved in a de-gassed mixture of toluene (1 mL) and butanol (1 mL) and added to the other reagents. The reaction mixture was heated to 10° C. for 48 hours. The reaction mixture was allowed to cool to room temperature, water was added in a test tube, a small amount of ethyl acetate was added, and the organic layer was decanted off and filtered through a plug of silica and eluted with ethyl acetate. The solvent was removed under reduced pressure to yield the crude material. Analytical LCMS method 1, retention time 5.01 min, M+H=413. The product was used in the next step without further purification.
  • 5
  • [ 35450-36-3 ]
  • [ 89488-25-5 ]
  • [ 1238196-95-6 ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); water; caesium carbonate In 1,2-dimethoxyethane at 125℃; for 0.25h; Inert atmosphere; Microwave irradiation; Combinatorial reaction / High throughput screening (HTS);
  • 6
  • [ 89488-25-5 ]
  • [ 1354787-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr 5.1: potassium carbonate / dimethyl sulfoxide / 18 h / 20 °C
  • 7
  • [ 89488-25-5 ]
  • [ 1354786-47-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr 5.1: potassium carbonate / dimethyl sulfoxide / 2 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C
  • 8
  • [ 89488-25-5 ]
  • [ 1354787-42-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr 5.1: potassium carbonate / dimethyl sulfoxide / 2 h / 20 °C
  • 9
  • [ 89488-25-5 ]
  • [ 1354786-52-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr 5.1: potassium carbonate / dimethyl sulfoxide / 20 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C
  • 10
  • [ 89488-25-5 ]
  • [ 1354787-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr 5.1: potassium carbonate / dimethyl sulfoxide / 20 h / 20 °C
  • 11
  • [ 89488-25-5 ]
  • [ 1354787-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube 4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 18 h / 60 °C / 2585.81 Torr
  • 12
  • [ 89488-25-5 ]
  • [ 1354787-47-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C 3.1: potassium carbonate; tetra(n-butyl)ammonium hydroxide / tri tert-butylphosphoniumtetrafluoroborate; bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide / N,N-dimethyl-formamide; methanol / 3 h / 130 °C / Microwave irradiation; Sealed tube
  • 13
  • [ 89488-25-5 ]
  • [ 1354787-48-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 2.2: 18 h / 60 °C
  • 14
  • [ 1197294-80-6 ]
  • [ 89488-25-5 ]
  • [ 1235407-20-1 ]
YieldReaction ConditionsOperation in experiment
66% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 70℃; for 18h;Inert atmosphere; <strong>[1197294-80-6]tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate</strong> (1.00 g, 2.66 mmol), 5-chloro-2-hydroxyphenylboronic acid (458 mg, 2.66 mmol) and sodium carbonate (1.13 g, 10.64 mmol) were combined and dissolved in a mixture of dioxane/water (14 mL/4 mL). The reaction mixture was degassed for 20 min with nitrogen and then tetrakistriphenylphosphinepalladium (0) (153 mg, 0.133 mmol) was added. The reaction mixture was heated at 70 C. for 18 hours and then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was separated, washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (10% to 60% ethyl acetate in heptane over 20 CV) to give the title compound (700 mg, 66%) as a white solid.1H NMR (400 MHz, CD3OD): delta 1.40 (s, 9H), 3.50 (s, 8H), 6.80-6.90 (m, 2H), 6.95 (s, 1H), 7.15 (d, 1H), 7.30 (s, 1H), 8.05 (d, 1H).LCMS Rt=2.48 minutes MS m/z 388 [M-H]-.
  • 15
  • [ 3934-20-1 ]
  • [ 89488-25-5 ]
  • [ 1207535-01-0 ]
YieldReaction ConditionsOperation in experiment
7% With sodium carbonate In 1,2-dimethoxyethane; water at 85℃; for 4h; Inert atmosphere; 1 A mixture of 2,4-dichloropyrimidine (0.765 g, 5.03 mmol), (5-chloro-2- hydroxyphenyl)boronic acid (0.568 g, 3.30 mmol), 2.0 M aqueous sodium carbonate (2.82 mL, 5.64 mmol), and 1 ,2-dimethoxyethane (8 mL) was sparged for 10 minutes with argon. Tetrakis(triphenylphosphine)palladium(0) (0.217 g, 0.19 mmol) was added, and the resultant mixture was heated for 4 hours at 85 °C. The reaction mixture mixture was cooled to 0 °C, quenched with saturated aqueous ammonium chloride solution, and extracted with dichloromethane (x 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by automated silica gel flash chromatography (hexanes to ethyl acetate gradient elution) to afford the title compound as a yellow solid (61 .5 mg, 7%). 1 HNMR (de-DMSO): δ 7.06 (d, 1 H), 7.45 (m, 1 H), 8.00 (d, 1 H), 8.28 (d, 1 H), 8.81 (d, 1 H), 1 1 .21 (s, 1 H).LCMS Rt = 1 .74 min MS m/z 241 [MH]+
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