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[ CAS No. 858131-73-4 ] {[proInfo.proName]}

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Chemical Structure| 858131-73-4
Chemical Structure| 858131-73-4
Structure of 858131-73-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 858131-73-4 ]

CAS No. :858131-73-4 MDL No. :MFCD28978624
Formula : C24H18BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YVBMFCFOASRILM-UHFFFAOYSA-N
M.W : 363.22 Pubchem ID :58892383
Synonyms :

Calculated chemistry of [ 858131-73-4 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 25
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 116.04
TPSA : 45.39 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 5.53
Log Po/w (WLOGP) : 4.13
Log Po/w (MLOGP) : 3.7
Log Po/w (SILICOS-IT) : 2.97
Consensus Log Po/w : 3.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.04
Solubility : 0.000332 mg/ml ; 0.000000915 mol/l
Class : Poorly soluble
Log S (Ali) : -6.24
Solubility : 0.000208 mg/ml ; 0.000000572 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.01
Solubility : 0.00000356 mg/ml ; 0.0000000098 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.47

Safety of [ 858131-73-4 ]

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 [ 858131-73-4 ]

* 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 [ 858131-73-4 ]

[ 858131-73-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 858131-73-4 ]
  • [ 6484-25-9 ]
  • C38H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 9h; Heating / reflux; 1.1 A 100 ml three neck flask was charged with 1.68 g (7 mmol) of 2-phenyl-4-chloroquinazoline (catalogue No. 16,243-4 manufactured by Aldrich Corp.), 2.80 g (7.7 mmol) of 4'-(N-carbazolyl)biphenyl borate and 0.243 g (0.21 mmol, 3 mol % Pd) of tetrakis-(triphenylphosphine)palladium (0), and the inside of the vessel was substituted with argon. Further, 26 ml of 1,2-dimethoxyethane and 12.5 ml (3 eq) of a 2M sodium carbonate aqueous solution were added thereto, and the mixture was heated and refluxed on an oil bath of 90°C for 9 hours. After finishing the reaction, resulting powder was taken by filtering to obtain 3.27 g of the compound (H-1). The compound (H-1) thus obtained was measured for FD-MS (field desorption mass spectrum), and the result thereof is shown below. FD-MS: calculated for C38H25N3 = 524, found m/z=524 (M+,100) The compound (H-1) obtained was further refined by sublimation (340°C, 2 × 10-3 Pa) and used for production of an organic EL device.
  • 2
  • [ 121-43-7 ]
  • [ 207447-27-6 ]
  • [ 7732-18-5 ]
  • [ 858131-73-4 ]
YieldReaction ConditionsOperation in experiment
62% With n-C4H9Li; NH4Cl In tetrahydrofuran; cyclohexane (N2); n-C4H9Li in cyclohexane added dropwise to C12H8N(C6H4)2I in THF at-78°C, kept for 30 min, warmed to room temp. for 1 h, B(OCH3)3 a dded at -78°C, stirred for 30 min, warmed to room temp. and stirred overnight, aq. NH4Cl added; extd. (CH2Cl2), evapd., chromd. (silica gel, CH2Cl2/MeOH), evapd., dissolved in THF, added dropwise to HCl soln. (pH 5), filtered, dried; elem. anal.;
  • 3
  • [ 858131-73-4 ]
  • [ 195813-56-0 ]
  • [ 1233923-44-8 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In benzene for 15h; Reflux;
75% With (C2H5)3N In benzene (N2); a mixt. of (HOC6H4)2C5H3N, B compd., and (C2H5)3N in C6H6 refluxed; evapd., chromd. (silica gel, cyclohexane/CH2Cl2); elem. anal.;
  • 4
  • [ 858131-73-4 ]
  • [ 89583-92-6 ]
  • [ 1262866-89-6 ]
YieldReaction ConditionsOperation in experiment
50% With sodium carbonate In ethanol; water; toluene at 120℃; for 3h; 3 After 4-chloropyrido[4,3-d]pyrimidin (2.5 g, 15.0 mmol), 3-(9H- carbazole-9-one)biphenylboronic acid (8.1 g, 22.5 mmol), Pd(PPh3)4693 mg(0.60 mmol), sodium carbonate aqueous solution (52 mL), and ethanol (52 mL) were dissolved in toluene (100 mL) , the mixture was stirred under reflux at 120 °C for 3 hours. After extracting with ethyl acetate when the reaction was completed, remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 89 (3 g, 6.69 mmol, 50 %)
  • 5
  • [ 207447-27-6 ]
  • [ 858131-73-4 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 9-(4'-iodine-[1,1'-biphenyl]-4-yl)-9H-carbazole With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 20℃; for 1.5h; Stage #2: With Trimethyl borate In tetrahydrofuran; cyclohexane at -78 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; cyclohexane
  • 6
  • [ 858131-73-4 ]
  • [ 956034-07-4 ]
  • [ 98-80-6 ]
  • C36H23N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 13h; Inert atmosphere; Reflux; Step2: synthesis of compound (A-5) General procedure: Intermediate product A 20.0 g (50.5 mmol), 4 - phenylboronic Acid 7.39 g (60.6 mmol) and K2CO3 16.8 g (121 mmol), Pd (PPh3) 4 2.92 g (2.53 mmmol) and THF 400 ml, distilled water 200 It was suspended in a stream of nitrogen mlReflux for 13 hours and stirred. After the reaction was cooled and the precipitated solid was filtered. Methanol and the solid several times with water and dried after ssikeun dichloromethane (methylene chloride: MC) and hexane (n-hexane: n-Hex) by recrystallization to obtain a compound (A-5) 18.4g (yield: 83%) was obtained .To the specific compounds according to the embodiment of thepresent invention prepared according to the synthetic methods as describedabove it is shown in Table 1 below.
  • 7
  • [ 21848-84-0 ]
  • [ 858131-73-4 ]
  • C36H24BNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.2% Stage #1: 1-bromo-2-[(2-bromophenyl)thio]benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: (4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)boronic acid at -78 - 20℃; for 6h; 9 Example 9 20 g of compound 3-6, 200 ml of tetrahydrofuran (THF) were added to a 500 ml three-necked flask.The air in the reaction flask was replaced with nitrogen, and the temperature was lowered to -78 ° C, and 60 ml of n-BuLi (2.0 M in THF) was slowly added dropwise under nitrogen protection.The reaction was kept at this temperature for 2 h.43.2 g of 4'-(9-carbazolyl)-biphenyl-4-boronic acid was added,Maintain this temperature and continue to react to room temperature after 6 hours.When the raw material reaction is complete,Add 1M ammonium chloride solution to adjust the pH to neutral, stir for 10 min, and then stand still.The organic phase was dried over anhydrous Na 2 SO 4 for 2 h and filtered.The filtrate was concentrated and passed through a silica gel column to give compound 3-8 as a white solid 17.4 g.The yield was 58.2%.
  • 8
  • [ 858131-73-4 ]
  • 4'-bromo-5'-phenyl-[1,1':2',1''-terphenyl]-4-carbonitrile [ No CAS ]
  • C49H32N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Inert atmosphere; Reflux; 5 Intermediate 3 (2.136 g, 1.5 mmol), compound 8 (1.416 g, 3.9 mmol), anhydrous potassium carbonate (1.616 g, 11.7 mmol) and Pd (PPh3) 4 (225 mg, 0.195 mmol) were added to a 250 mL reaction flask. Under nitrogen protection, 10 mL of THF and 5 mL of water were added, and the mixture was refluxed overnight. The reaction was cooled, extracted with dichloromethane, concentrated, and then filtered to give a white solid CzPh-TPB-CN, yield 89%.
  • 9
  • [ 858131-73-4 ]
  • [ 877615-05-9 ]
  • C51H32N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux; 10 Synthesis Example 10 Synthesis of Comparative Compound R2 6 g (13.46 mmol) of the intermediate F synthesized in Synthesis Example 9 and5.13 g (14.13 mmol) of 4- (9H-carbazole-9-yl) biphenyl boronic acid, 0.47 g (0.40 mmol) of Pd (PPh3) 4,3.72 g (26.91 mmol) of K 2 CO 3 is suspended in 50 ml of THF 100 ml distilled water and stirred under reflux for 12 hours.After the reaction was completed, the produced solid was filtered and washed with distilled water / acetone. After heating and dissolving in 300 ml of dichlorobenzene, the filtrate was cooled to room temperature by Silicagel filter and the resulting solid was filtered and dried to obtain 3.9 g (40% yield) of the comparative compound R2.
  • 10
  • [ 858131-73-4 ]
  • C19H10Cl2N2S [ No CAS ]
  • C67H42N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; caesium carbonate In 1,4-dioxane at 80 - 90℃; for 4h; Inert atmosphere; 13 Example 11 Synthesis of Compound I-16 General procedure: 1L three-neck flask, equipped with magnetic stirring, add M1 (40.2g, 0.1mol),(9-Phenyl-9H-carbazol-3-yl)boronic acid (86.1g, 0.3mol), cesium carbonate (117g, 0.36mol) and dioxane 400ml, start stirring.After nitrogen replacement again (2.2 g, 11 mmol) tri-tert-butyl phosphine and (4.1 g, 4.5 mmol) tris(dibenzylideneacetone) dipalladium were added.After the addition, the temperature is increased, and the temperature is controlled at 80-90°C to react for 4 hours. After the reaction, the temperature is lowered.Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin-dry the solvent to obtain 79.8 g of light yellow solid, the yield is about 78%.
  • 11
  • [ 858131-73-4 ]
  • C19H10BrClN2S [ No CAS ]
  • C43H26ClN3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 78℃; for 3h; Inert atmosphere; 19 In a 1L three-necked bottle, add M9 (41.2g, 0.1mol),(4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)boronic acid (36.3g, 0.1mol),Sodium carbonate (21.2g, 0.2mol), 150mL toluene, 150mL ethanol, 150mL water,Pd(PPh3)4 (11.5g, 0.01mol) was added after the reaction system was replaced with nitrogen for protection.The reaction was heated and refluxed (temperature in the system was about 78°C) for 3 hours to stop the reaction.Reduce the evaporation of the solvent, extract with dichloromethane, dry with anhydrous magnesium sulfate, filter, and column chromatography with petroleum ether/ethyl acetate (2:1),The solvent was spin-dried, slurried with ethyl acetate, and filtered to obtain 53.4 g of light yellow solid I-174-1 with a yield of about 82%.
  • 12
  • [ 858131-73-4 ]
  • C29H18ClN3 [ No CAS ]
  • C53H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.2% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In ethanol; water; toluene at 80℃; for 6h; Inert atmosphere; (12) Compound 51 Add 10g intermediate 3 and 8.2g compound 50-1 into a three-necked flask,4.7g potassium carbonate,1.4g tetra-tert-butylammonium bromide, 180ml toluene, 60ml ethanol,30ml water and nitrogen gas,Then 0.65 g of tetrakis(triphenylphosphine)palladium was added.The reaction solution was heated to 80°C, refluxed and stirred for 6 hours,After TLC monitors the complete reaction of the raw materials, the temperature drops to room temperature,The reaction solution was washed with water to neutrality, and the organic phase was dried with anhydrous sodium sulfate and purified by silica gel column.The crude product obtained by concentrating the eluent was recrystallized from toluene to obtain 11.3 g of compound 51.The yield was 69.2%.
  • 13
  • [ 858131-73-4 ]
  • C20H14BrN [ No CAS ]
  • C44H30N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 24h; Inert atmosphere; General formula for synthesis of M1-M7 and M15-M21 monomers: General procedure: Weigh out raw material 2 (5mmol), R1-B(OH)2 (6mmol), and dissolve them with a mixed solvent of toluene and ethanol at a volume ratio of 2:1; under an inert atmosphere, add an aqueous solution of Na2CO3 (20ml; moles of Na2CO3) The concentration is 0.5mol/L) and the catalyst Pd(PPh3)4 (0.3mmol); the mixed solution of the above reactants is reacted at 120°C for 24 hours, cooled and filtered, the filtrate obtained is rotary evaporated and purified by silica gel column chromatography, The target product A1 is obtained; the yield is about 75%.
  • 14
  • [ 858131-73-4 ]
  • [ 1246562-40-2 ]
  • N-[4''-(9H-carbazol-9-yl)-1,1′:4′,1''-terphenyl-4-yl]-N-(1,1′-biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In toluene at 60℃; for 10h; Reflux; Synthesis of YGTBiF(2)> Into a 200 mL three-neck flask equipped with a reflux pipe, 2.0 g (4.0 mmol) of 2-amino-N-[(1,1′-biphenyl)-4-yl]-N-(4-bromophenyl)-9,9-dimethylfluorene, 1.4 g (4.0 mmol) of [4′-(carbazol-9-yl)-4-biphenylyl]boronic acid, 24 mg (76 μmol) of tri(ortho-tolyl)phosphine, 5 mL of a 2M potassium carbonate solution, 30 mL of toluene, and 10 mL of ethanol were put, the mixture was degassed under reduced pressure, and the air in the system was replaced with nitrogen. This mixture was heated at 60° C., and 8.9 mg (40 μmol) of palladium(II) acetate was added thereto. This mixture was refluxed for 10 hours. The obtained mixture was suction-filtered. Water was added to the obtained filtrate, and an aqueous layer was subjected to extraction with toluene. The extracted solution was combined with an organic layer, and the resulting mixture was washed with water and saturated saline and dried with magnesium sulfate. This mixture was gravity-filtered, and the obtained filtrate was concentrated to give a pale brown solid. This solid was purified by high performance liquid chromatography (HPLC) (mobile phase: chloroform) to give 1.3 g of a target pale yellow solid in a yield of 43%. (0407) By a train sublimation method, 1.3 g of the obtained solid was purified. In the sublimation purification, the solid was heated at 350° C. for 15 hours under a pressure of 3.1 Pa with an argon flow rate of 15 mL/min. After the sublimation purification, 1.1 g of a target pale yellow solid was obtained at a collection rate of 85%. Synthesis Scheme (Y-1) is shown below. (0408) Analysis results by 1H NMR of the obtained pale yellow solid are shown below. The results show that YGTBiF(2) was obtained. (0409) 1H NMR (dichloromethane-d2, 300 MHz): δ=8.17 (d, J=7.8 Hz, 2H), 7.92 (d, J=8.7 Hz, 2H), 7.75 (dd, J1=27.6 Hz, J2=9.0 Hz, 4H), 7.70-7.61 (m, 8H), 7.56 (d, J=9.0 Hz, 2H), 7.52-7.42 (m, 7H), 7.36-7.24 (m, 10H), 7.14 (dd, J1=6.0 Hz, J2=2.1 Hz, 1H), 1.45 (s, 6H).
  • 15
  • [ 858131-73-4 ]
  • C28H13ClO4S2 [ No CAS ]
  • C52H29NO4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; caesium carbonate In 1,4-dioxane at 85 - 90℃; for 4h; Inert atmosphere; 12 Take a 1L three-necked flask with magnetic stirring, add I-42-01 (51.2g, 0.1mol), [4'-(carbazol-9-yl)biphenyl-4-yl]boronic acid (36.3g) after nitrogen replacement , 0.1mol), cesium carbonate (39g, 0.12mol) and 400ml of dioxane, start stirring. After nitrogen replacement again (0.8 g, 4 mmol) tri-tert-butyl phosphine and (1.4 g, 1.5 mmol) tris(dibenzylideneacetone) dipalladium were added. After the addition, the temperature is increased by heating, and the temperature is controlled at 80-90°C for 4 hours, and the temperature is decreased after the reaction is completed. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin-dry the solvent to obtain 55.5 g of light yellow solid I-42 with a yield of 69.8%.
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