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[ CAS No. 2567-29-5 ] {[proInfo.proName]}

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Chemical Structure| 2567-29-5
Chemical Structure| 2567-29-5
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Product Details of [ 2567-29-5 ]

CAS No. :2567-29-5 MDL No. :MFCD00017869
Formula : C13H11Br Boiling Point : -
Linear Structure Formula :- InChI Key :HZQLUIZFUXNFHK-UHFFFAOYSA-N
M.W : 247.13 Pubchem ID :257716
Synonyms :

Calculated chemistry of [ 2567-29-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.71
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 4.82
Log Po/w (WLOGP) : 4.1
Log Po/w (MLOGP) : 4.54
Log Po/w (SILICOS-IT) : 4.57
Consensus Log Po/w : 4.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.91
Solubility : 0.00303 mg/ml ; 0.0000123 mol/l
Class : Moderately soluble
Log S (Ali) : -4.55
Solubility : 0.00692 mg/ml ; 0.000028 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.18
Solubility : 0.000165 mg/ml ; 0.000000667 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.02

Safety of [ 2567-29-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3261
Hazard Statements:H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2567-29-5 ]

* 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 [ 2567-29-5 ]
  • Downstream synthetic route of [ 2567-29-5 ]

[ 2567-29-5 ] Synthesis Path-Upstream   1~22

  • 1
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YieldReaction ConditionsOperation in experiment
95% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h; Carbon tetrabromide (8.99 g, 27.1 MMOL) and triphenyl phosphine (7.11 g, 27.1 MMOL) were added to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 MMOL) in dichloromethane (100 mL) at room temperature. Stirring was continued at room temperature for 1.5 hours then the solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel (1: 20 diethyl ether: cyclohexane) to give the title compound (6.37g, 95percent) as a white solid.'H NMR (400 MHz: CDCI3) : 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
95% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h; Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) wereadded to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) indichloromethane (100 ml_) at room temperature. Stirring was continued at room temperaturefor 1.5 hours then the solvent removed by evaporation under reduced pressure. Theresidue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37g, 95percent) as a white solid. 1H NMR (400 MHz:CDCI3): 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
91% With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 1 h; General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
75% With phosphorus tribromide In chloroform; di-isopropyl ether Reference Example 50
4-Phenylbenzyl Bromide
To a solution of 4-phenylbenzyl alcohol (1.00 g, 5.43 mmol) in a mixture of diisopropyl ether (10 mL) and chloroform (20 mL) was added phosphorus tribromide (0.98 g, 3.62 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour.
This reaction mixture was diluted with water and extracted with diisopropyl ether.
The organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered.
The filtrate was concentrated under reduced pressure and the residue was recrystallized from ethanol-hexane to provide 1.00 g of the title compound.
Yield 75percent.
m.p. 86-88° C.
1H-NMR (CDCl3) δ: 4.55 (2H, s), 7.32-7.67 (9H, m).

Reference: [1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Patent: WO2005/26120, 2005, A1, . Location in patent: Page/Page column 21
[3] Patent: WO2004/110974, 2004, A1, . Location in patent: Page 22
[4] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[6] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171
[7] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 10, p. 535 - 548
[8] Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026
[9] Organic Letters, 2012, vol. 14, # 11, p. 2754 - 2757
[10] Tetrahedron Letters, 2001, vol. 42, # 32, p. 5571 - 5573
[11] Patent: US6248766, 2001, B1,
[12] Carbohydrate Research, 1982, vol. 105, p. 168 - 172
[13] Mendeleev Communications, 2007, vol. 17, # 2, p. 82 - 84
[14] Helvetica Chimica Acta, 1952, vol. 35, p. 1348,1351
[15] Journal of Organic Chemistry, 1961, vol. 26, p. 2662 - 2667
[16] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5177 - 5183
[17] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 12, p. 2067 - 2080
[18] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
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[22] Patent: WO2006/90235, 2006, A1, . Location in patent: Page/Page column 46
[23] Patent: US6399629, 2002, B1,
[24] Patent: US2008/194565, 2008, A1, . Location in patent: Page/Page column 17
[25] Patent: US2003/225158, 2003, A1, . Location in patent: Page 22-23
[26] Organic Letters, 2013, vol. 15, # 22, p. 5818 - 5821
  • 2
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  • [ 98-80-6 ]
  • [ 2567-29-5 ]
YieldReaction ConditionsOperation in experiment
82.4% With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; To a dry 250 mL three-necked flask was added phenylboronic acid (2.44 g, 0.02 mol), p-bromobenzyl bromide (4.99 g, 0.02 mol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol).Add anhydrous potassium carbonate (8.28 g, 0.06 mol), and 50 mL of toluene, 30 mL of absolute ethanol,10 mL of deionized water was further added with sodium borohydride (0.57 g, 15 mmol), and the mixture was heated to 100 ° C in an oil bath. After the reaction was confirmed by thin-plate chromatography, silica gel column chromatography was performed with ethyl acetate and n-hexane system to collect the product, 4.07. g, yield 82.4percent.
73% With C24H20Cl2NPPdS; potassium carbonate; palladium In toluene at 100℃; for 24 h; General procedure: A 100 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer bar. The flask was charged with toluene (15 ml) and the appropriate amount of catalyst reagents and the internal standard (n-Decane: 2.59 mmol). The contents were thoroughly mixed and an initial sample (t0) was then taken. The reaction flask was placed in an oil bath at the desired temperature and the reaction mixture allowed to heat/reflux with stirring. A sample was taken and analyzed every 10 min for the first hour and every 30 min thereafter until t3h. In cases where conversionwas not complete after 3 h, the reaction mixturewas then allowed to stir for a total of 24 h. The reaction at 140 °C was performed in a sealed tube. All catalytic reactions were done under aerobic conditions. Percentage conversions were determined by GC with n-decane as the internal standard and the coupling products were characterized by mass spectrometry (Table 4) as well as 1H NMR spectroscopy (Entry 5, Table 4 only).
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6959 - 6962
[2] Patent: CN107522643, 2017, A, . Location in patent: Paragraph 0101-0103; 0107; 0108
[3] Journal of Organometallic Chemistry, 2012, vol. 703, p. 34 - 42
  • 3
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[5] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[6] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 21, p. 2735 - 2740
[7] European Journal of Organic Chemistry, 2009, # 36, p. 6328 - 6335
[8] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[9] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
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[11] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6492 - 6499
[12] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 4
  • [ 16004-15-2 ]
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6959 - 6962
  • 5
  • [ 5728-52-9 ]
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Reference: [1] Organic Letters, 2017, vol. 19, # 7, p. 1634 - 1637
  • 6
  • [ 768-59-2 ]
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Reference: [1] ChemMedChem, 2011, vol. 6, # 5, p. 904 - 921
  • 7
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  • [ 202264-90-2 ]
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[2] Patent: US6235778, 2001, B1,
[3] Chemistry - A European Journal, 2014, vol. 20, # 40, p. 12750 - 12753
  • 8
  • [ 92-92-2 ]
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Reference: [1] Journal of Organic Chemistry, 1961, vol. 26, p. 2662 - 2667
[2] Organic Letters, 2013, vol. 15, # 22, p. 5818 - 5821
  • 9
  • [ 589-15-1 ]
  • [ 98-80-6 ]
  • [ 613-42-3 ]
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Reference: [1] Applied Organometallic Chemistry, 2011, vol. 25, # 3, p. 173 - 179
  • 10
  • [ 108-86-1 ]
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[2] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
  • 11
  • [ 5720-05-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[2] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
  • 12
  • [ 4748-78-1 ]
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Reference: [1] ChemMedChem, 2011, vol. 6, # 5, p. 904 - 921
  • 13
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6492 - 6499
  • 14
  • [ 106-38-7 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6492 - 6499
  • 15
  • [ 92-52-4 ]
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  • [ 20248-86-6 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 983
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Reference: [1] Journal of the Indian Chemical Society, 1930, vol. 7, p. 95,109
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Reference: [1] Journal of Organic Chemistry, 1961, vol. 26, p. 2662 - 2667
  • 18
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  • [ 7726-95-6 ]
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Reference: [1] Journal of the Indian Chemical Society, 1930, vol. 7, p. 95,109
  • 19
  • [ 506-68-3 ]
  • [ 861342-35-0 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 315
  • 20
  • [ 506-68-3 ]
  • [ 262371-18-6 ]
  • [ 34065-04-8 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 315
  • 21
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 315
  • 22
  • [ 506-68-3 ]
  • [ 861376-27-4 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 315
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