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[ CAS No. 191089-06-2 ]

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Chemical Structure| 191089-06-2
Chemical Structure| 191089-06-2
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Product Details of [ 191089-06-2 ]

CAS No. :191089-06-2 MDL No. :MFCD09037832
Formula : C8H9BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :179.97 g/mol Pubchem ID :-
Synonyms :

Safety of [ 191089-06-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 191089-06-2 ]

  • Downstream synthetic route of [ 191089-06-2 ]

[ 191089-06-2 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 191089-06-2 ]
  • 2-methyl-4-(3-methyl-pyridin-2-yl)-<i>N</i>-(4-trifluoromethyl-phenyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BOP / CH2Cl2 2: aq. Na2CO3; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 80 °C
  • 3
  • [ 5419-55-6 ]
  • [ 68837-59-2 ]
  • [ 191089-06-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Triisopropyl borate; 4-bromo-2-methylbenzoic acid With n-butyllithium In tetrahydrofuran Stage #2: In tetrahydrofuran Acidic conditions;
  • 4
  • [ 191089-06-2 ]
  • [ 1899-24-7 ]
  • [ 1052597-25-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene for 3h; Reflux;
  • 5
  • [ 191089-06-2 ]
  • [ 947248-68-2 ]
  • [ 1309682-28-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid,; 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine With potassium carbonate In propan-1-ol for 1h; Reflux; Stage #2: With hydrogenchloride In water Int11.1 Intermediate [Example Intl 1.14- 2-amino[1 , 2, 4]triazolo[1 ,5-a] pyridin-6-yl)-2-methyl benzoic acidTo a stirred solution of Int1.2 (1 .45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic aci (1 .22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1 H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).
With potassium carbonate In propan-1-ol for 1h; Reflux; Int05.01 Intermediate Example Int05.01; 4- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acid To a stirred solution of Int01.02 (1.45 g) in 1 -propanol (65 ml) was added 2M potassium carbonate solution (10 ml), 4-carboxy-3-methylphenylboronic acid (1.22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).
Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid,; 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine With potassium carbonate In propan-1-ol for 1h; Reflux; Stage #2: With hydrogenchloride In water Intermediate Example Int7.14- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acid To a stirred solution of Int 1.2 (1.45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic acid (1.22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).
With potassium carbonate In propan-1-ol 05.01 Intermediate Example Int05.014- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acidTo a stirred solution of Int01.02 (1.45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic acid (1 .22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).

  • 6
  • [ 191089-06-2 ]
  • [ 1082604-63-4 ]
  • [ 1464154-85-5 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; 74.1 Step 1 : To a solution of 4-(6-chloroimidazo[l,2-b]pyridazin-3-yl)benzonitrile (200 mg, 0.67 mmol) in a mixture of DMF (4 mL) and water (lmL) blanketed with nitrogen, was successively added K2C03 (185 mg, 1.34 mmol), Pd(dppf)Cl2 (98 mg, 0.13 mmol) and 4- borono-2-methylbenzoic acid (131 mg, 0.73 mmol). The reaction mixture was stirred at 80 °C for 18 h, then was diluted with water (10 mL) and extracted with DCM (3 χ 10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the crude 4-(3-(4-cyanophenyl)imidazo[l,2-b]pyridazin-6-yl)-2- methylbenzoic acid (271 mg) as black solid which was used carried forth to the next step without further purification. MS (ESI) m/z 355 [C21Hi4FN402 + H ]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; 74.1 Example 74 To a solution of 4-(6-chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile (200 mg, 0.67 mmol) in a mixture of DMF (4 mL) and water (1 mL) blanketed with nitrogen, was successively added K2CO3 (185 mg, 1.34 mmol), Pd(dppf)Cl2 (98 mg, 0.13 mmol) and 4-borono-2-methylbenzoic acid (131 mg, 0.73 mmol). The reaction-mixture was stirred at 80° C. for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude 4-(3-(4-cyanophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-methylbenzoic acid (271 mg) as black solid which was used carried forth to the next step without further purification. MS (ESI) m/z 355 [C21H14FN4O2+H]+.
  • 7
  • [ 191089-06-2 ]
  • [ 1025065-97-7 ]
  • [ 1464155-30-3 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; 83.1 Step 1 : To a solution of 6-chloro-3-(4-chlorophenyl)imidazo[l,2-b]pyridazine (308 mg, 1.00 mmol) in a mixture of DMF (4 mL) and water (lmL), were successively added K CO3 (138 mg, 1.00 mmol), Pd(dppf)Cl2 (146 mg, 0.20 mmol) and 4-borono-2-methylbenzoic acid (198 mg, 1.10 mmol). The reaction mixture was stirred at 80 °C for 18 h under inert atmosphere, then was diluted with water (10 mL) and extracted with DCM (3x10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under vacuum to afford the crude 4-(3-(4-chlorophenyl)imidazo[l,2-b]pyridazin-6-yl)-2-methylbenzoic acid (724 mg) as black solid. MS (ESI) m/z 364 [C20H14ClN3O2 + H ]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; 83.1 Example 83 To a solution of 6-chloro-3-(4-chlorophenyl)imidazo[1,2-b]pyridazine (308 mg, 1.00 mmol) in a mixture of DMF (4 mL) and water (1 mL), were successively added K2CO3 (138 mg, 1.00 mmol), Pd(dppf)Cl2 (146 mg, 0.20 mmol) and 4-borono-2-methylbenzoic acid (198 mg, 1.10 mmol). The reaction mixture was stirred at 80° C. for 18 h under inert atmosphere, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford the crude 4-(3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-methylbenzoic acid (724 mg) as black solid. MS (ESI) m/z 364 [C20H14ClN3O2+H]+.
  • 8
  • [ 191089-06-2 ]
  • [ 1464153-49-8 ]
  • [ 1464153-68-1 ]
YieldReaction ConditionsOperation in experiment
83% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide for 18h; Inert atmosphere; Reflux; 27.2 Example 27 4-borono-2-methylbenzoic acid (100 mg, 0.55 mmol), K2CO3 (138 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.1 mg, 0.01 mmol) were added sequentially to a solution of 4-(6-bromoimidazo[1,2-a]pyrazin-3-yl)benzonitrile (150 mg, 0.50 mmol) in DMF at room temperature under inert atmosphere. The reaction mixture was refluxed for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-methylbenzoic acid (105 mg, 83%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) 12.87 (bs, 1H), 9.31 (s, 1H), 9.07 (s, 1H), 8.24 (s, 1H), 8.10-8.04 (m, 5H), 8.02 (d, J=8.2 Hz, 1H), 7.94 (d, J=8.2 Hz, 1H), 2.62 (s, 3H); MS (ESI) m/z 355 [C21H14N4O2+H]+.
105 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; 27.2 Step 2: 4-borono-2-methylbenzoic acid (100 mg, 0.55 mmol), 2C03 (138 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.1 mg, 0.01 mmol) were added sequentially to a solution of 4-(6- bromoimidazo[l,2-a]pyrazin-3-yl)benzonitrile (150 mg, 0.50 mmol) in DMF at room temperature under inert atmosphere. The reaction mixture was refluxed for 18 h, then was diluted with water (10 mL) and extracted with DCM (3x10 mL). The combined organic layers were dried over Na S04, filtered and concentrated under reduced pressure to afford 4- (3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2-methylbenzoic acid (105 mg, 83 %) as a brown solid. 1H NMR (400 MHz, DMSO- 12.87 (bs, 1H), 9.31 (s, 1H), 9.07 (s, 1H), 8.24 (s, 1H), 8.10 - 8.04 (m, 5H), 8.02 (d, J= 8.2 Hz, 1H), 7.94 (d, J= 8.2 Hz, 1H), 2.62 (s, 3H); MS (ESI) m/z 355 [C21H14N402 + H ]+.
  • 10
  • [ 191089-06-2 ]
  • 2-methyl-4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 72 h / 105 °C 2: sodium carbonate; palladium dichloride / 1,4-dioxane / 15 h / 100 °C 3: potassium carbonate / methanol / 65 h / 50 °C
  • 11
  • [ 191089-06-2 ]
  • C27H20N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 72 h / 105 °C 2: sodium carbonate; palladium dichloride / 1,4-dioxane / 15 h / 100 °C
  • 12
  • [ 191089-06-2 ]
  • C39H36Br3Cl6N6O3 [ No CAS ]
  • C63H57Cl6N6O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With 2'-dicyclohexyl-2,6-dimethoxy-3-(sulfonic acid)-1,1'-biphenyl sodium; potassium carbonate; palladium dichloride In water at 100℃; for 36h; Schlenk technique; Inert atmosphere; 2.2 (2) Preparation of nitrite-containing aryltriphenyl (triazine) tricarboxylic acid (22) Under a protective atmosphere of inert gas (high purity nitrogen), 1 mmol of the nitrogen-containing oxygen radical-triarylbenzene (triazine) bromide (24) obtained in the step (1) is added to a 50 ml Schlek reaction tube, 6mmol 3-methyl-4-p-carboxybenzeneboronic acid, 0.15 mmol of palladium chloride, 0.18 mmol of 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 6 mmol of potassium carbonate and 30 ml of water, The reaction tube was replaced with nitrogen three times, then heated to 100 ° C with an oil bath under magnetic stirring, and the reaction was refluxed for 36 h; The oil bath was removed, the reaction was filtered, the filtrate was acidified, the pH was adjusted to 1 with concentrated hydrochloric acid, and stirred at 20 ° C for 1 h, filtered, and dried. A pure product containing a nitroxyl radical, a ternary arylbenzene (triazine)tricarboxylic acid (22) was obtained, and the structural formula was as follows, and the yield was 66%.
  • 13
  • [ 191089-06-2 ]
  • C42H48Br3N6O3 [ No CAS ]
  • C66H69N6O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2'-dicyclohexyl-2,6-dimethoxy-3-(sulfonic acid)-1,1'-biphenyl sodium; potassium carbonate; palladium dichloride In water at 100℃; for 36h; Schlenk technique; Inert atmosphere; 6.2 (2) Preparation of nitrite-containing aryl benzene ((triazine)) tricarboxylic acid (29) Under the protection of inert gas (high purity nitrogen), add 1 mmol of the nitrogen-containing oxygen radical-triarylbenzene (triazine) bromide obtained in the step (1) to a 50 ml Schlek reaction tube, and 6 mmol 3-methyl-4. - p-carboxyphenylboronic acid, 0.15 mmol of palladium chloride, 0.22 mmol of 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 6 mmol of potassium carbonate and 30 ml of water, The reaction tube was replaced with nitrogen three times, then heated to 100 ° C with an oil bath under magnetic stirring, and the reaction was refluxed for 36 h; The oil bath was removed, the reaction was filtered, the filtrate was acidified, the pH was adjusted to 1 with concentrated hydrochloric acid, and stirred at 25 ° C for 1 h, then filtered. The obtained solid was dried to obtain a pure product nitrogen-oxygen radical-containing ternary arylbenzene (triazine)tricarboxylic acid (29) having the structural formula shown below, and the yield was 76%.
  • 14
  • [ 191089-06-2 ]
  • [ 506-59-2 ]
  • [4-(dimethylcarbamoyl)-3-methylphenyl]boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid, With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: N,N-dimethylammonium chloride In N,N-dimethyl-formamide at 20℃; for 3h; 10.1 Step 1: Intermediate 7 -- [4-(Dimethylcarbamoyl)-3-methyl-phenyl]boronic acid . [0457] 4-Carboxy-3-methylphenylboronic acid (500 mg, 2.78 mmol) was dissolved in DMF (4 mL). DIPEA (2.9 mL, 16.67 mmol) and HATU (1.27 g, 3.33 mmol) were added and the resulting mixture was stirred at rt for 10 min. Dimethylamine HC1 (453 mg, 5.56 mmol) was added and the mixture stirred at rt for 3 h. Half-saturated aq. NH4CI (50 mL) and EtOAc (50 mL) were added, the organic layer was separated and the aqueous layer extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated to give the product (954 mg, 83%, 50% purity), which was used in the next step without further purification. MS ES+ m z 208 [M+H]+.
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