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[ CAS No. 25487-66-5 ] {[proInfo.proName]}

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Chemical Structure| 25487-66-5
Chemical Structure| 25487-66-5
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Product Details of [ 25487-66-5 ]

CAS No. :25487-66-5 MDL No. :MFCD00036833
Formula : C7H7BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :DBVFWZMQJQMJCB-UHFFFAOYSA-N
M.W :165.94 Pubchem ID :2733957
Synonyms :

Calculated chemistry of [ 25487-66-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 43.23
TPSA : 77.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.35
Log Po/w (WLOGP) : -0.94
Log Po/w (MLOGP) : -0.13
Log Po/w (SILICOS-IT) : -1.35
Consensus Log Po/w : -0.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.33
Solubility : 7.81 mg/ml ; 0.0471 mol/l
Class : Very soluble
Log S (Ali) : -1.55
Solubility : 4.71 mg/ml ; 0.0284 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.65
Solubility : 36.8 mg/ml ; 0.222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 25487-66-5 ]

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

Application In Synthesis of [ 25487-66-5 ]

* 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.

  • Upstream synthesis route of [ 25487-66-5 ]
  • Downstream synthetic route of [ 25487-66-5 ]

[ 25487-66-5 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 109-04-6 ]
  • [ 25487-66-5 ]
  • [ 4467-07-6 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In water; acetonitrile at 100℃; for 24 h; Inert atmosphere Example 161 A3-(pyridin-2-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100° C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85percent. LC-MS (ESI) m/z: 200 (M+1)+.
Reference: [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 75
  • 2
  • [ 1120-87-2 ]
  • [ 25487-66-5 ]
  • [ 4385-78-8 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In water; acetonitrileReflux Example 165 A3-(pyridin-4-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 4-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g 3-(pyridin-4-yl)benzoic acid. Yield: 83percent. LC-MS (ESI) m/z: 200 (M+1)+.
Reference: [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 76
  • 3
  • [ 25487-66-5 ]
  • [ 19524-06-2 ]
  • [ 4385-78-8 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 3, p. 1089 - 1095
  • 4
  • [ 25487-66-5 ]
  • [ 618-51-9 ]
YieldReaction ConditionsOperation in experiment
78% With iodine; potassium carbonate In acetonitrile at 80℃; for 8 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v
Reference: [1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
[2] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
  • 5
  • [ 150255-96-2 ]
  • [ 25487-66-5 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With potassium hydroxide In ethylene glycol at 175℃; for 3 h;
Stage #2: With hydrogenchloride In water; ethylene glycol
1.
Preparation of 3-carboxyphenylboronic acid
10 g (68 mmol) of 3-cyanophenylboronic acid and 15.26 g (272 mmol, 4 eq.) of potassium hydroxide powder were suspended in 40 ml of ethylene glycol and heated to 175° C.
After three hours, the reaction mixture was allowed to cool and was diluted with 60 ml of water.
The pH was adjusted to 2-3 with 32percent hydrochloric acid, which precipitated the 3-carboxyphenylboronic acid in colorless crystalline form, which was isolated by filtering it off with suction.
The crystals were washed with water and dried under a gentle vacuum at 35° C.
The yield was 10.04 g (60.5 mmol, 89percent).
Reference: [1] Patent: US2009/286995, 2009, A1, . Location in patent: Page/Page column 4
  • 6
  • [ 7722-64-7 ]
  • [ 17933-03-8 ]
  • [ 25487-66-5 ]
YieldReaction ConditionsOperation in experiment
61.2% With sodium hydroxide In water at 30 - 40℃; 250 ml of aqueous sodium hydroxide solution (30percent) was added to the reaction flask, 0.90 mol of 3-methylphenylboronic acid was prepared as described above, and the temperature was controlled to 30-40° C. under stirring. Potassium permanganate 1.50 mol ( 1.7eq) was added in batches, feeding was completed, and the reaction was incubated until the reaction of the raw materials was complete, suction filtration, rotary evaporation, acidification, suction filtration, and beating purification to obtain 0.612 mol 3-carboxyphenylboronic acid as a white solid, purity 99.5percent, yield 61.2percent .
Reference: [1] Patent: CN106946924, 2017, A, . Location in patent: Paragraph 0011; 0019; 0021; 0022; 0024; 0025; 0027
  • 7
  • [ 17933-03-8 ]
  • [ 25487-66-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 153,169,170
[2] Patent: US5183653, 1993, A,
[3] Tetrahedron, 1963, vol. 19, p. 821 - 826
[4] J. Prakt. Chem. (2), 1930, vol. 128, p. 153 - 170
[5] Liebigs Annalen der Chemie, 1901, vol. 315, p. 26 - 40
[6] Arkiv foer Kemi, 1957, vol. 10, p. 473 - 482
[7] Arkiv foer Kemi, 1957, vol. 10, p. 513 - 521
[8] Journal of the American Chemical Society, 1934, vol. 56, p. 1865 - 1870
[9] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 8
  • [ 124-38-9 ]
  • [ 98527-70-9 ]
  • [ 25487-66-5 ]
YieldReaction ConditionsOperation in experiment
110 g
Stage #1: With iodine; magnesium In tetrahydrofuran at 40 - 70℃; Inert atmosphere
Stage #2: at -20℃;
Under nitrogen, in a 2 L three-necked flask, 26.7 g (1.1 mol) of metallic magnesium and several small grains of iodine were added, followed bySlowly add 600 ml solution of the m-bromophenylboronic acid trimer in anhydrous tetrahydrofuran obtained as described above, and add about 30-50 ml of the solution dropwise to the solution and raise the temperature to 40-45 ° C. To be triggered by the reaction, the disappearance of iodine color, and then the rest of the solution slowly added dropwise temperature does not exceed 70 is appropriate. The reaction was then kept for 2-5 hours and the reaction was confirmed complete. Then the system was cooled to -20 ° C, began to slowly access the carbon dioxide gas, the system to maintain a certain pressure until the pressure drops, and then continue to access the carbon dioxide gas. This process takes about 4-8 hours, added to maintain the temperature to continue stirring the reaction 1-3 hours, then naturally rose to room temperature and stirred for 3-5 hours. After completion of the TLC detection reaction, the system was cooled to 0 ° C and quenched by addition of 10percent aqueous hydrochloric acid to adjust the pH to 2-3. At this point, a large amount of solid was precipitated in the system. After filtration, drying gave p-carboxyphenylboronic acid 110 as a white solidG, HPLC: 98.0percent, total yield 66percent for two steps.
Reference: [1] Patent: CN104844643, 2017, B, . Location in patent: Paragraph 0027; 0028
  • 9
  • [ 124-38-9 ]
  • [ 626-00-6 ]
  • [ 25487-66-5 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 18, p. 3171 - 3178
  • 10
  • [ 13675-18-8 ]
  • [ 99-05-8 ]
  • [ 25487-66-5 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
  • 11
  • [ 535-80-8 ]
  • [ 25487-66-5 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
  • 12
  • [ 13675-18-8 ]
  • [ 25487-66-5 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 13
  • [ 99-05-8 ]
  • [ 25487-66-5 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 14
  • [ 64-17-5 ]
  • [ 25487-66-5 ]
  • [ 4334-87-6 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 5068
[2] Arkiv foer Kemi, 1957, vol. 10, p. 497,503
  • 15
  • [ 25487-66-5 ]
  • [ 101084-81-5 ]
YieldReaction ConditionsOperation in experiment
63% for 0.5 h; Cooling with ice The 7.5g between 5-carboxyphenylboronic acid(45.2mmol) by adding 25 ml of concentrated sulfuric acid, under rapid stirring state by adding 25 ml fuming nitric acid, ice water bath cooling. Stirring the reaction 15 min evacuation de-ice water bath, to continue reaction 15 min. In ice water into the reaction liquid, precipitate, filtering, washing 5 times, re-crystallization with water, to obtain white solid 3-nitro-5-carboxyl phenylo boric acid 6.01g, yield 63.0percent ; the 1.50g3-carboxy-5-nitro-phenylboronic acid (7.1mmol), 20 ml methanol, 10percent Pd/C0 . 2g by adding 50 ml in three-necked bottle, catalytic hydrogenolysis 6h. Filtered to remove palladium-carbon, the filtrate is evaporated to dryness, to obtain white powder solid 3-amino-5-carboxyl phenylo boric acid 1.25g, yield 97.1percent.
Reference: [1] Patent: CN103497211, 2016, B, . Location in patent: Paragraph 0190
[2] Organic Preparations and Procedures International, 1991, vol. 23, # 6, p. 729 - 734
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 3017
[4] Arkiv foer Kemi, 1957, vol. 10, p. 497,503
  • 16
  • [ 626-55-1 ]
  • [ 25487-66-5 ]
  • [ 4385-77-7 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In water; acetonitrileReflux Example 163 A3-(pyridin-3-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g of 3-(pyridin-3-yl)benzoic acid. Yield: 83percent. LC-MS (ESI) m/z: 200 (M+1)+.
Reference: [1] Synlett, 2000, # 6, p. 829 - 831
[2] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 76
[3] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1853 - 1863
[4] Patent: JP5743418, 2015, B2, . Location in patent: Paragraph 0142; 0143; 0144
  • 17
  • [ 67-56-1 ]
  • [ 25487-66-5 ]
  • [ 99769-19-4 ]
YieldReaction ConditionsOperation in experiment
97.1% at 55 - 65℃; Autoclave; Industrial scale In a 20L reactor, 8.0 Kg of anhydrous methanol was added and carboxylbenzene acid 1.66 Kg (10 mol), stirring the reactor was heated to 55 , temperature 55 ~ 65 thionyl chloride was added dropwise to the kettle (1.78 Kg, 15 mol), dropwise after the reaction warmed to reflux for 2-3 hours.After completion of the reaction was confirmed (TLC: n-heptane: ethyl acetate = 2: 1), the reaction solution was cooled, the solvent evaporated under reduced pressure, after adding heptane, cooled -10 ~ 0 , stirred for 1 hour was filtered, Save 80 The solid was dried pressure until no impurities confirmation HNMR (HNMR: DMSO-d6In 3.16ppm peak) to stop drying.Water was added after stirring at room temperature was filtered, dried at room temperature to give a white solid 1.75Kg, 97.1percent yield.
Reference: [1] Patent: CN106188117, 2016, A, . Location in patent: Paragraph 0015
  • 18
  • [ 25487-66-5 ]
  • [ 4595-60-2 ]
  • [ 579476-26-9 ]
Reference: [1] Synlett, 2000, # 6, p. 829 - 831
  • 19
  • [ 25487-66-5 ]
  • [ 376592-93-7 ]
Reference: [1] Patent: WO2013/49605, 2013, A1,
[2] Patent: EP2799425, 2014, A1,
[3] Patent: WO2014/177517, 2014, A1,
  • 20
  • [ 76-09-5 ]
  • [ 25487-66-5 ]
  • [ 269409-73-6 ]
YieldReaction ConditionsOperation in experiment
91% for 4 h; General procedure: The boronic acids 26 and 27 (0.667 mmol) were dissolved in 6 mL of ethyl acetate and, stirring the solution, pinacol (0.667 mmol) was added. After 4 h the reaction was stopped adding anhydrous Na2SO4 (1 g) and CaCl2 (1 g). The mixture was filtered and concentrated in vacuo (Yields: 91percent of 28 and 89percent of 29).
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 311 - 323
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 16, p. 5012 - 5016
  • 21
  • [ 25487-66-5 ]
  • [ 15969-10-5 ]
  • [ 376592-58-4 ]
Reference: [1] Patent: WO2013/49605, 2013, A1, . Location in patent: Paragraph 0055
  • 22
  • [ 25487-66-5 ]
  • [ 376592-58-4 ]
Reference: [1] Patent: WO2013/49605, 2013, A1,
  • 23
  • [ 4595-59-9 ]
  • [ 25487-66-5 ]
  • [ 852180-74-6 ]
Reference: [1] Patent: WO2005/58837, 2005, A1, . Location in patent: Page/Page column 16
  • 24
  • [ 4487-59-6 ]
  • [ 25487-66-5 ]
  • [ 864075-95-6 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In ethanol; water; toluene for 48 h; Heating / reflux 2-Bromo-5-nitropyridine (1.96g, 9. 6mmol) and 3- carboxybenzeneboronic acid (1.8g, 10. 8mmol, l. lequiv. ) were dissolved in a mixture of toluene (40mL), ethanol (40mL) and water (5mL) and potassium carbonate (4.1g, 29.3mmol, 3. 0equiv.) was added. The flask was purged with nitrogen gas then palladium tetrakis (triphenylphosphine) (0.2g) was added and the mixture heated at reflux for 48 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (lOOmL) and extracted with water (3 x 50mL). The aqueous extracts were combined and washed with dichloromethane (3 x 50mL). The aqueous fraction was acidified (pH 1-2) with concentrated hydrochloric acid to give an off white precipitate, which was collected on a filter and dried under vacuum to give a white solid 18,2. 132g (91percent). 1H-NMR (d6-DMSO) 8 13.21 (1H, bs, CO2H), 9.46 (1H, d, J = 2.7Hz, H- 6'), 8.75 (1H, dd, J= 1. 6Hz, H-2), 8.66 (1H, dd, J = 2.7, 8.8Hz, H-4'), 8.42 (1H, ddd, J = 1.2, 1.9, 7.9Hz, H-6), 8.33 (1H, dd, J = 8.8Hz, H-3'), 8.10 (1H, m, H-4), 7.69 (1H, dd, J = 7.8Hz, H-5); 13C NMR (d6-DMSO) 8 166.8, 159.9, 144.9 (CH), 143.3, 136.9, 132.8 (CH), 131.7, 131.6 (CH), 131.3 (CH), 129.5 (CH), 128.2 (CH), 120.8 (CH); LCMS RT = 3.00 min, (M--l) = 243.
Reference: [1] Patent: WO2005/85177, 2005, A2, . Location in patent: Page/Page column 50-51
  • 25
  • [ 3934-20-1 ]
  • [ 25487-66-5 ]
  • [ 937271-47-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 169 - 196
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2404 - 2408
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 9, p. 2284 - 2288
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