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Product Details of [ 34699-28-0 ]

CAS No. :34699-28-0 MDL No. :MFCD20257904
Formula : C26H19Br Boiling Point : -
Linear Structure Formula :- InChI Key :MYJLJYSALGARCM-UHFFFAOYSA-N
M.W :411.33 Pubchem ID :24882208
Synonyms :

Calculated chemistry of [ 34699-28-0 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 118.49
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.22
Log Po/w (XLOGP3) : 8.65
Log Po/w (WLOGP) : 7.46
Log Po/w (MLOGP) : 7.19
Log Po/w (SILICOS-IT) : 7.34
Consensus Log Po/w : 6.97

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -8.23
Solubility : 0.0000024 mg/ml ; 0.0000000058 mol/l
Class : Poorly soluble
Log S (Ali) : -8.53
Solubility : 0.00000122 mg/ml ; 0.000000003 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.8
Solubility : 0.0000000065 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.8

Safety of [ 34699-28-0 ]

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 [ 34699-28-0 ]

* 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 [ 34699-28-0 ]
  • Downstream synthetic route of [ 34699-28-0 ]

[ 34699-28-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 101-81-5 ]
  • [ 90-90-4 ]
  • [ 34699-28-0 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With n-butyllithium In tetrahydrofuran for 1.33333 h; Inert atmosphere; Cooling with ice
Stage #2: at 20℃; for 12 h;
16.7 mL (0.1 mol) of diphenylmethane and 300 ml of tetrahydrofuran (THF) were added to a solution of500ml three-necked flask, magnetic stirring and argon, ice salt bath 40min, to the three bottles by adding 54.5mL (0.12mol) n-butyl lithium solution, continue ice salt bath 40min, add 13.0555g4-bromobenzophenone(Bis (4-bromophenyl) methanone, 0.05),After the reaction was carried out at room temperature for 12 h, 250 ml of saturated ammonium chloride (NH4Cl) solution was added to the three-necked flask. After stirring for 10 min, the reaction solution was poured into a separatory funnel, the supernatant was taken and the water in the solution was adsorbed with 300 g of anhydrous sodium sulfate. And then heated to 110 ° C. After adding 5 g of p-toluenesulfonic acid, the mixture was refluxed for 12 hours. After the reaction was stopped, the reaction solution was dried and dried. The reaction mixture was heated to 110 ° C, The product was spin dried to dry the powder and the powder was dried in vacuo at 60 ° C for 24 h to give the white intermediate Si-Br in 89percent yield.
73.03%
Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 6 h;
Stage #3: With toluene-4-sulfonic acid In tolueneReflux
1, under the conditions of a temperature of 0 ° C, the 100ml three-necked flask was evacuated and filled with N2 three times,12 mmol of diphenylmethane and 50 ml of dehydrated tetrahydrofuran were evacuated, and 10 mmol of n-butyllithium was gradually introduced into the flask. While maintaining the atmosphere of nitrogen at 0 ° C, n-butyllithium was subjected to dehydrogenation for 1 hour. To the solution was added 9.5 mmolBromobenzophenone, the reaction was allowed to return to room temperature and stirred for 6 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride. The organic phase was extracted with CH 2 Cl 2, washed three times with saturated brine and dried over anhydrous Na 2 SO 4. The organic solvent , The residue,Toluenesulfonic acid and 60 ml of toluene were added to a 100 ml two-necked flask, and the mixture was refluxed for 6-8 hours. The mixture was cooled to room temperature and the organic layer was washed with 10percent aqueous NaHCO 3 solution Three times, the combined organic phases were dried over anhydrous Na2SO4 and the solvent toluene was evaporated under reduced pressure. The residue was purified by column chromatography to give a white solid Product 1-1. Yield: 73.03percent. 1-1
66%
Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: at 20℃; for 6 h;
Stage #3: With toluene-4-sulfonic acid In toluene at 110℃;
In a 250 mL three-necked flask,Diphenylmethane (10.0 g, 59.5 mmol) was dissolved in 150 mL of re-distilled tetrahydrofuran,At 0 slowly added dropwise n-BuLi (25mL, 2.5M),After reaction for 30 min, 4-bromobenzoylbenzene (5.2 g, 20.0 mmol) was slowly added dropwise.Then, the temperature was raised to room temperature for 6 h, quenched with ammonium chloride,The reaction was extracted with CH2Cl2 (3 x 20 mL) and the extract was washed with water (3 x 20 mL)Dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to give an alcohol.The above alcohol solution was dissolved with toluene,P-toluenesulfonic acid (1.7 g, 0.01 mol) was added,The reaction was carried out at 110 ° C for 3-4 h with a water distilling apparatus.The reaction was extracted with sodium bicarbonate. The extract was washed with water (3 x 20 mL) and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the column was separated (PE) to give 5.3 g of product (yield: 66percent) as a white solid.
64%
Stage #1: With n-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 10 h;
Stage #3: With toluene-4-sulfonic acid In toluene for 5 h; Reflux
1. Add 10.09 g (0.06 mol) of diphenylmethane to a 500 mL three-necked flask.And 250 mL of dry tetrahydrofuran, vacuum replacement, cooling to 0 ° C,Maintain mixing,Slowly add to the mixture with a syringe under nitrogen protection24.0 mL of 2.5 mol/L (0.06 mol) n-butyllithium in cyclohexane solution,Stirring was continued for 30 min after the addition, and then 40 mL of a dry tetrahydrofuran solution containing 15.14 g (0.058 mol) of 4-bromobenzophenone was added dropwise.After stirring at room temperature for 10 h, the reaction mixture was quenched with aqueous ammonium chloride, and extracted with dichloromethane (300 mL×3×),Rinse alternately with saturated aqueous sodium chloride solution and deionized water (300 mL × 3 times).Dry with anhydrous magnesium sulfate, filter, and distill off the solvent.The intermediate 2-(4-bromophenyl)-1,1,2-triphenylethanol was obtained.The obtained intermediate was dissolved in 300 mL of toluene with 1.0 g of anhydrous p-toluenesulfonic acid.After refluxing for 5 h, toluene was distilled off, and the obtained solid was dissolved in 300 mL of dichloromethane.Then alternately wash with saturated aqueous sodium chloride solution and deionized water (300mL×3 times).Drying anhydrous magnesium sulfate, filtering, and distilling off the solvent to obtain a crude product;Taking cyclohexane/dichloromethane (v/v=5:1) as the eluent,The crude product was separated by silica gel column chromatography.15.27g of white solid 1-(4-bromophenyl)-1,2,2-triphenylethylene,The yield was 64percent.
37%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 6 h;
Stage #3: With toluene-4-sulfonic acid In toluene for 16 h; Reflux
Step 1, synthesis of bromotetraphenylethene (TPE-Br)
The benzylbenzene (2.0g, 11.9mmol) was dissolved in 20mL of anhydrous tetrahydrofuran, was stirred at 0°C under nitrogen atmosphere, 1.6M n-hexane solution of n-butyllithium (7.4mL, 11.9mmol) was slowly added, reacted for 30 minutes; and then 4-bromo-benzophenone (3.1g, 11.9mmol) was added, slowly warmed to room temperature and the reaction mixture was stirred for 6 hours, followed by addition of a small amount of water to the reaction solution for the reaction to stop, the reaction solution was extracted twice with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate and was filtered. The solvent was distilled off under reduced pressure. The resulting solid was dissolved in 80mL of toluene, p-toluenesulfonic acid monohydrate (500mg, 2.6mmol, catalyst) was added, and refluxed for 16 hours, the reaction was cooled to room temperature and extracted twice with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate and was filtered. The solvent was distilled off under reduced pressure. The crude product with hexane as a mobile phase and the silica gel as the stationary phase was pass through column chromatography, obtaining a white solid 1.8g, 37percent yield;

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[2] Patent: CN107082753, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032; 0033; 0034; 0035
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[5] Patent: CN106565595, 2017, A, . Location in patent: Paragraph 0028; 0033; 0034; 0035
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[15] Patent: CN108250205, 2018, A, . Location in patent: Paragraph 0043; 0044; 0045; 0052; 0059
  • 2
  • [ 1391632-33-9 ]
  • [ 34699-28-0 ]
YieldReaction ConditionsOperation in experiment
1.2 g With toluene-4-sulfonic acid In toluene for 3 h; Inert atmosphere; Schlenk technique; Dean-Stark; Reflux n-Butyllithium (1.6 mol/L, 10 mmol) was added dropwise to a solutionof diphenylmethane (1.77 g, 10.5 mmol) in anhydrous THF(50 mL) at 0 °C. The reaction mixture was stirred for 0.5 h, and thenturned to red before (4-bromophenyl)phenylmethanone (3.38 g,10 mmol) was added in one portion. The mixture was warmed to roomtemperature, stirred for 6 h and then was poured into water whilestirring. The mixture was extracted with dichloromethane (3 × 50 mL)and the combined extracts were dried over anhydrous MgSO4. Thesolvent was evaporated and the resultant crude alcohol 4 (containingexcess diphenylmethane) was subjected to acid-catalyzed dehydrationas follows. Compound 4 was dissolved in toluene (50 mL) in a 100 mLSchlenk flask fitted with a Dean-Stark trap. A catalytic amount of ptoluenesulfonicacid (342 mg, 1.8 mmol) was added and the mixturewas refluxed for 3 h. After cooled to room temperature, the toluenelayer was washed with 10percent aqueous NaHCO3 solution (2×25 mL) anddried over anhydrous MgSO4. The solvent was evaporated under reducedpressure the crude product was purified with column chromatographyon silica gel with petroleum ether/dichloromethane (15:1) aseluent to afford a residue of 5 (1.2 g) in yield of 63percent. mp 216–218 °C.1H NMR (400 MHz, CDCl3) δ (ppm): 7.25–7.20 (d, J = 8.06 Hz, 2H),7.17–7.08 (m, 9H), 7.07–6.99 (m, 6H), 6.94–6.87 (d, J = 8.14 Hz, 2H).13C NMR (100 MHz, CDCl3), δ (ppm): 148.06, 143.19, 143.14, 143.09,141.75, 140.63, 134.72, 132.62, 131.21, 130.78, 130.69, 127.62,127.54, 126.37, 126.23. Anal. Calcd for C26H19Br: C, 75.92; H, 4.66.Found: C, 76.14; H, 4.52.
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[2] Chemical Communications, 2012, vol. 48, # 62, p. 7711 - 7713
[3] Dyes and Pigments, 2018, vol. 149, p. 399 - 406
  • 3
  • [ 589-87-7 ]
  • [ 501-65-5 ]
  • [ 98-80-6 ]
  • [ 34699-28-0 ]
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  • 4
  • [ 101-81-5 ]
  • [ 34699-28-0 ]
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[34] Chemistry - An Asian Journal, 2017, vol. 12, # 18, p. 2501 - 2509
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  • 5
  • [ 90-90-4 ]
  • [ 34699-28-0 ]
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[2] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 660 - 663
[3] Journal of Materials Chemistry, 2011, vol. 21, # 6, p. 1788 - 1796
[4] Journal of Materials Chemistry, 2012, vol. 22, # 35, p. 18505 - 18513
[5] Chemical Communications, 2011, vol. 47, # 39, p. 11080 - 11082
[6] Advanced Materials, 2010, vol. 22, # 19, p. 2159 - 2163
[7] Journal of Materials Chemistry, 2012, vol. 22, # 15, p. 7387 - 7394
[8] Journal of Materials Chemistry, 2012, vol. 22, # 15, p. 7515 - 7528
[9] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[10] Chemistry of Materials, 2012, vol. 24, # 11, p. 2178 - 2185
[11] Chemical Communications, 2012, vol. 48, # 62, p. 7711 - 7713
[12] Tetrahedron Letters, 2012, vol. 53, # 50, p. 6838 - 6842
[13] Dyes and Pigments, 2013, vol. 96, # 2, p. 391 - 396
[14] Chemical Communications, 2013, vol. 49, # 15, p. 1503 - 1505
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[16] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3388 - 3393
[17] Advanced Functional Materials, 2013, vol. 23, # 18, p. 2329 - 2337
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[20] Chemical Communications, 2014, vol. 50, # 14, p. 1725 - 1727
[21] Advanced Functional Materials, 2014, vol. 24, # 5, p. 635 - 643
[22] RSC Advances, 2014, vol. 4, # 37, p. 19418 - 19421
[23] Chemical Communications, 2014, vol. 50, # 65, p. 9076 - 9078
[24] Organic and Biomolecular Chemistry, 2015, vol. 13, # 13, p. 4090 - 4100
[25] Journal of Materials Chemistry B, 2015, vol. 3, # 15, p. 3091 - 3097
[26] Macromolecules, 2015, vol. 48, # 4, p. 1038 - 1047
[27] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 3832 - 3840
[28] Journal of Materials Chemistry C, 2015, vol. 3, # 20, p. 5162 - 5166
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  • 6
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  • 9
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  • 11
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