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[ CAS No. 61326-44-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 61326-44-1
Chemical Structure| 61326-44-1
Chemical Structure| 61326-44-1
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Product Details of [ 61326-44-1 ]

CAS No. :61326-44-1 MDL No. :MFCD00667761
Formula : C26H16Br4 Boiling Point : -
Linear Structure Formula :- InChI Key :BIRLDGKMJJEZRI-UHFFFAOYSA-N
M.W : 648.02 Pubchem ID :11828419
Synonyms :

Calculated chemistry of [ 61326-44-1 ]

Physicochemical Properties

Num. heavy atoms : 30
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 : 141.59
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.37
Log Po/w (XLOGP3) : 10.73
Log Po/w (WLOGP) : 9.74
Log Po/w (MLOGP) : 8.85
Log Po/w (SILICOS-IT) : 9.34
Consensus Log Po/w : 8.81

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -10.95
Solubility : 0.0000000073 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -10.69
Solubility : 0.0000000134 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -13.08
Solubility : 0.0000000001 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 [ 61326-44-1 ]

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 [ 61326-44-1 ]

* 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 [ 61326-44-1 ]
  • Downstream synthetic route of [ 61326-44-1 ]

[ 61326-44-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 632-51-9 ]
  • [ 61326-44-1 ]
YieldReaction ConditionsOperation in experiment
76% for 168 h; [0085] 1) 1,1,2,2-tetrakis(4-bromophenyl)ethene (A). 75mmol (25G) 1,1,2,2- tetraphenylethene was placed in a watch glass on the rack of a desiccator. 585mmo1 (30m1) bromide liquid was poured in the bottom of the desiccator. The desiccator was closed with a small hole leaving to release HBr formed from the reaction. After 7 days, the yellow solid was collected and recrystallized with dichloromethane/methanol (2:1) to give white crystals. Yield:37g, 76percent. 1H NMR (CDC13, 300MHz, 298K): ö6.84 (d, 8H, Hf3ArH), 7.26 (d, 8H, HcLArH). Additional peaks: ö7.26 (m, CDC13), öl.6 (m, H20).
50% With bromine In toluene at 20℃; for 24 h; Compound 1 was synthesized by modifying the previously reportedprocedures [44]. TPE (6.0 g, 18.0 mmol) was treated with bromine(7.5 mL, 0.15mol) in a flask for 24 h at roomtemperature. The resultingsolid was dissolved in hot toluene (120 mL), and the solution was isolatedin hexane. The resulting crude product was purified by flashsilica-gel column chromatography (eluent: hexane) to yield 1 (5.27 g,50percent) as white solid. 1H NMR (500 MHz, CDCl3, δ): 7.26 (d, J = 8.6 Hz,8H), 6.84 (d, J = 8.6 Hz, 8H).
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10064 - 10067
[2] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9415 - 9423
[3] Journal of the American Chemical Society, 2017, vol. 139, # 50, p. 18142 - 18145
[4] Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8390 - 8394
[5] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12565 - 12574
[6] Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 729 - 733[7] Angew. Chem., 2018, vol. 130, # 3, p. 737 - 741,5
[8] Tetrahedron Letters, 2009, vol. 50, # 45, p. 6159 - 6162
[9] Chemical Communications, 2014, vol. 50, # 96, p. 15243 - 15246
[10] Journal of Materials Chemistry B, 2015, vol. 3, # 36, p. 7222 - 7226
[11] Journal of Materials Chemistry C, 2018, vol. 6, # 46, p. 12601 - 12607
[12] Journal of the American Chemical Society, 2015, vol. 137, # 31, p. 9963 - 9970
[13] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 27, p. 4470 - 4475
[14] Journal of Materials Chemistry A, 2018, vol. 6, # 43, p. 21542 - 21549
[15] RSC Advances, 2018, vol. 8, # 60, p. 34291 - 34296
[16] Journal of the American Chemical Society, 2014, vol. 136, # 48, p. 16724 - 16727
[17] Patent: WO2015/164784, 2015, A1, . Location in patent: Paragraph 0084; 0085
[18] Chemical Communications, 2013, vol. 49, # 38, p. 3961 - 3963
[19] Journal of the American Chemical Society, 2014, vol. 136, # 23, p. 8269 - 8276
[20] Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5797 - 5800
[21] Journal of the American Chemical Society, 2011, vol. 133, # 44, p. 17622 - 17625
[22] Chemical Communications, 2016, vol. 52, # 85, p. 12602 - 12605
[23] Molecules, 2018, vol. 23, # 2,
[24] Journal of Materials Chemistry A, 2014, vol. 2, # 34, p. 13831 - 13834
[25] European Journal of Organic Chemistry, 2003, # 15, p. 2829 - 2839
[26] Tetrahedron Letters, 2011, vol. 52, # 19, p. 2519 - 2522
[27] Chemical Communications, 2017, vol. 53, # 52, p. 7048 - 7051
[28] Journal of Molecular Liquids, 2018, vol. 265, p. 260 - 268
[29] Journal of the American Chemical Society, 1916, vol. 38, p. 707
[30] Justus Liebigs Annalen der Chemie, 1897, vol. 296, p. 245
[31] Justus Liebigs Annalen der Chemie, 1904, vol. 337, p. 200
[32] Journal of Organic Chemistry, 1961, vol. 26, p. 670 - 679
[33] Tetrahedron Letters, 1990, vol. 31, # 50, p. 7367 - 7370
[34] Crystal Growth and Design, 2015, vol. 15, # 7, p. 3271 - 3279
[35] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16209 - 16215
[36] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 3, p. 3102 - 3105
[37] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8922 - 8926
[38] Journal of Materials Chemistry A, 2016, vol. 4, # 35, p. 13450 - 13457
[39] Chemistry - An Asian Journal, 2017, vol. 12, # 5, p. 615 - 620
[40] Patent: CN107141250, 2017, A, . Location in patent: Paragraph 0013; 0014
[41] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14743 - 14748[42] Angew. Chem., 2017, vol. 129, # 46, p. 14938 - 14943,6
[43] Chemistry - A European Journal, 2017, vol. 23, # 71, p. 18010 - 18018
[44] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 984 - 992
[45] Dyes and Pigments, 2017, vol. 146, p. 7 - 13
[46] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5750 - 5753[47] Angew. Chem., 2018, vol. 130, # 20, p. 5852 - 5855,4
  • 2
  • [ 3988-03-2 ]
  • [ 61326-44-1 ]
YieldReaction ConditionsOperation in experiment
76% With titanium tetrachloride; zinc In tetrahydrofuranReflux; Inert atmosphere General procedure: To a suspension of powder zinc (2.15 g, 33 mmol) in dry THF (40 mL) was added titanium(IV)chloride (1.81 mL, 16.5 mmol) dropwise under argon at 0 °C. The mixture was allowed to reflux for 4 h and then cooled to room temperature. A solution of (4-bromophenyl)phenylmethanone (980 mg, 4.12 mmol) and 4, 4′-dimethoxybenzophenone (1.0 g, 4.12 mmol) in THF (70 mL) was added to this suspension at once. Reaction mixture was heated to reflux for 5 h. The mixture was cooled to room temperature, quenched with 10percent aqueous K2CO3 solution (100 mL). The dispersed insoluble material was removed by vacuum filtration using a Celite® pad. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (3×50 mL), the combined organic fractions were washed with water (20 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the crude product, which was purified by column chromatography (silica gel/ethyl acetate: petroleum ether 1:5) afforded 4 (776 mg, 40percent) as a light yellow solid.
76% With titanium tetrachloride; zinc In tetrahydrofuran at -78℃; Inert atmosphere; Reflux 4,4'dibromobenzophenone(3.4 g, 10 mmol, 1.0 eq), zinc dust (1.6 g, 24 mmol, 2.4 eq) and 60 mL of dry tetrahydrofuran wereadded to a 250 mL threeneckedflask. After nitrogen was purged, the mixture was cooled in an acetone / liquid nitrogen bathat 78° C. TiCl4 (2.3 g, 12 mmol, 1.2 eq) was then slowly injected through the syringe into the reaction system. Aftercompletion of the system, the system was allowed to stand at room temperature for half an hour and then refluxed overnight.The reaction solution was stopped by filtration through a reduced pressure silica gel column to remove inorganic salts such aszinc and titanium. The filtrate was collected and spindriedto obtain a crude product which was recrystallized from methanol to give 2.5 g of white crystals in 76percent yield.
Reference: [1] Dalton Transactions, 2007, # 15, p. 1477 - 1480
[2] Journal of Materials Chemistry C, 2017, vol. 5, # 44, p. 11565 - 11572
[3] Tetrahedron Letters, 2012, vol. 53, # 50, p. 6838 - 6842
[4] Patent: CN104557552, 2016, B, . Location in patent: Paragraph 0051-0054
[5] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16028 - 16031
[6] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2003 - 2012
[7] Journal of Materials Chemistry C, 2014, vol. 2, # 26, p. 5155 - 5160
[8] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 644 - 651
[9] Chemistry - An Asian Journal, 2016, vol. 11, # 20, p. 2932 - 2937
[10] Patent: CN107188801, 2017, A, . Location in patent: Paragraph 0046-0048; 0057
[11] Patent: CN105037179, 2017, B, . Location in patent: Paragraph 0046-0048; 0055-0057; 0065-0067; 0075-0077
  • 3
  • [ 119-61-9 ]
  • [ 61326-44-1 ]
Reference: [1] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 3, p. 3102 - 3105
[2] Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8390 - 8394
[3] Patent: CN107141250, 2017, A,
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 729 - 733[5] Angew. Chem., 2018, vol. 130, # 3, p. 737 - 741,5
[6] Journal of the American Chemical Society, 2017, vol. 139, # 50, p. 18142 - 18145
[7] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5750 - 5753[8] Angew. Chem., 2018, vol. 130, # 20, p. 5852 - 5855,4
[9] Journal of Materials Chemistry A, 2018, vol. 6, # 43, p. 21542 - 21549
  • 4
  • [ 101-81-5 ]
  • [ 61326-44-1 ]
Reference: [1] American Chemical Journal, 1903, vol. 30, p. 465
  • 5
  • [ 1941-86-2 ]
  • [ 61326-44-1 ]
Reference: [1] American Chemical Journal, 1903, vol. 30, p. 465
  • 6
  • [ 1726-02-9 ]
  • [ 61326-44-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1904, vol. 337, p. 200
  • 7
  • [ 18066-91-6 ]
  • [ 61326-44-1 ]
Reference: [1] American Chemical Journal, 1903, vol. 30, p. 465
[2] American Chemical Journal, 1903, vol. 30, p. 465
  • 8
  • [ 7726-95-6 ]
  • [ 632-51-9 ]
  • [ 61326-44-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1897, vol. 296, p. 245
[2] Chemische Berichte, 1904, vol. 37, p. 3320
  • 9
  • [ 1600-30-2 ]
  • [ 7726-95-6 ]
  • [ 61326-44-1 ]
Reference: [1] Chemische Berichte, 1910, vol. 43, p. 2954
  • 10
  • [ 61326-44-1 ]
  • [ 1351279-73-6 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20126 - 20129
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8922 - 8926
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