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[ CAS No. 32316-92-0 ] {[proInfo.proName]}

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Chemical Structure| 32316-92-0
Chemical Structure| 32316-92-0
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Product Details of [ 32316-92-0 ]

CAS No. :32316-92-0 MDL No. :MFCD00236051
Formula : C10H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KPTRDYONBVUWPD-UHFFFAOYSA-N
M.W :171.99 Pubchem ID :2734375
Synonyms :

Calculated chemistry of [ 32316-92-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.77
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 0.52
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 0.34
Consensus Log Po/w : 0.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.328 mg/ml ; 0.00191 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.474 mg/ml ; 0.00276 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.189 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 32316-92-0 ]

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

Application In Synthesis of [ 32316-92-0 ]

* 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 [ 32316-92-0 ]
  • Downstream synthetic route of [ 32316-92-0 ]

[ 32316-92-0 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1354413-51-6 ]
  • [ 32316-92-0 ]
  • [ 36640-53-6 ]
Reference: [1] Arkivoc, 2011, vol. 2011, # 11, p. 1 - 21
  • 2
  • [ 201230-82-2 ]
  • [ 32316-92-0 ]
  • [ 613-56-9 ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; silver nitrate In acetone at 40℃; for 24 h; Autoclave; Inert atmosphere General procedure: The reaction was carried out in an autoclave containing a 10mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP(0.04 mmol), and a magnetic stir bar were placed in the tubewhich was then capped with a stopper and flushed withargon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),and acetone (3 mL) were added to the tube. The tube was putinto the autoclave. Once sealed, the autoclave was purgedseveral times with CO, pressurized to 1 atm at r.t. and thenheated in an oil bath at 40 °C for 24 h. The autoclave wasthen cooled to r.t. and carefully vented to discharge CO in afume hood. Water (10 mL) was added, and the product wasextracted with CH2Cl2 (3 × 15 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated. Thecrude product was purified by column chromatography onsilica gel using a mixture of EtOAc and PE as eluent to givethe products. The identity and purity of the product wasconfirmed by 1H NMR and 13C NMR spectroscopy and MSor HRMS spectrometry.
Reference: [1] Synlett, 2014, vol. 25, # 8, p. 1097 - 1100
  • 3
  • [ 119072-55-8 ]
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  • [ 613-56-9 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 15, p. 3954 - 3957
  • 4
  • [ 106-41-2 ]
  • [ 32316-92-0 ]
  • [ 6336-82-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 1075 - 1080
[2] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
  • 5
  • [ 540-38-5 ]
  • [ 32316-92-0 ]
  • [ 6336-82-9 ]
Reference: [1] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
  • 6
  • [ 118-48-9 ]
  • [ 32316-92-0 ]
  • [ 63449-68-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 22, p. 6114 - 6117
  • 7
  • [ 523-27-3 ]
  • [ 32316-92-0 ]
  • [ 474688-73-8 ]
YieldReaction ConditionsOperation in experiment
74% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 72 h; 9-Bromo-10-(naphthalen-2-yl)anthracene (Compound 1)
A mixture of 9,10-dibromoanthracene (16 g, 47.6 mmol), 2-naphthalenyl boronic acid (3.4 g, 19.8 mmol), Pd(PPh3)4 (1.0 g, 0.86 mmol) and sodium carbonate (8.4 g, 79 mmol) in tetrahydrofuran (THF)/water (200 ml/40 ml) was degassed and heated at about 80° C. for about 3 days.
After being cooled to room temperature, the mixture was filtered, and the filtrate was extracted with dichloromethane (DCM) (250 ml), then washed with brine.
The organic phase was collected and dried over Na2SO4, loaded on silica gel, purified by flash column (hexanes) to give a yellow solid (5.7 g, in 74percent yield).
64% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24 h; Inert atmosphere; Reflux 3.36 g (10 mmol) of 9,10-dibromoanthracene and 1.72 g (10 mmol) of Intermediate-1 were introduced under nitrogen and dissolved in 40 ml of toluene0.58 g (0.5 mmol) of Pd (PPh3) 4 and 15 ml (30 mmol) of 2M K2CO3 were added, respectively, and refluxed for 24 hours.After completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H2O were added to extract the MC layer,Dried over MgSO4, concentrated, and then subjected to column chromatography with Hex: EA = 4: 1 to obtain Intermediate-7 2.45 (64percent).
61% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 90℃; for 24 h; Inert atmosphere Synthesis of 9-bromo-10-(naphthalen-2-yl)anthracene
A mixture of 15 g (44.6 mmol) of 9,10-dibromoanthracene, 7.7 g (44.6 mmol) of naphthalen-2-ylboronic acid, 0.52 g (0.446 mmol) of Tetrakis(triphenylphosphine)Palladium, 33 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h.
After the reaction finish, the mixture was allowed to cool to room temperature.
The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 10.4 g (61percent) as a yellow solid.
3 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3 h; 2 - 5 g of 9, 10 - 50 ml of dimethoxyethane [jiburomoantorasen[jiburomoantorasen]naphthalene boron acid 2.1 g of commercially available and dissolved, was heated to 80 °C. 50 ml distilled water and sodium carbonate 10 g was placed therein. Further thereto was 0.4 g (0) tetrakistriphenylphosphine. 3 hours after the separatory funnel by extraction with toluene, silica (SiO2 500 g) was purified. Therefore, yellowish white crystals (9 - bromo-naphthalene - yl -10 - -2 - anthracene) 3 g was obtained as thin.

Reference: [1] Patent: US9923145, 2018, B2, . Location in patent: Page/Page column 34; 35
[2] Patent: KR2017/49295, 2017, A, . Location in patent: Paragraph 0151-0156
[3] Patent: US2014/131664, 2014, A1, . Location in patent: Paragraph 0035-0036
[4] Journal of Materials Chemistry, 2011, vol. 21, # 34, p. 12969 - 12976
[5] Patent: US2012/267615, 2012, A1, . Location in patent: Page/Page column 49
[6] Dyes and Pigments, 2013, vol. 96, # 1, p. 211 - 219
[7] Patent: JP6146001, 2017, B2, . Location in patent: Paragraph 0156-0157
[8] Patent: JP6145989, 2017, B2, . Location in patent: Paragraph 0140; 154
  • 8
  • [ 32316-92-0 ]
  • [ 474688-73-8 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2007, vol. 66, # 3, p. 672 - 675
[2] Dyes and Pigments, 2012, vol. 92, # 1, p. 588 - 595
[3] Patent: US2013/1539, 2013, A1,
[4] Patent: KR2016/12846, 2016, A,
[5] Patent: KR101548370, 2015, B1,
[6] Patent: KR2015/22269, 2015, A,
[7] Patent: KR101511379, 2015, B1,
[8] Patent: KR2015/22270, 2015, A,
[9] Patent: KR2016/22081, 2016, A,
[10] Patent: KR101502811, 2015, B1,
  • 9
  • [ 1564-64-3 ]
  • [ 32316-92-0 ]
  • [ 474688-73-8 ]
Reference: [1] Patent: US2011/54229, 2011, A1,
[2] Chemical Communications, 2013, vol. 49, # 41, p. 4664 - 4666
  • 10
  • [ 591-18-4 ]
  • [ 32316-92-0 ]
  • [ 667940-23-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In tetrahydrofuran for 24 h; Heating / reflux 2- A. Production of compound 2a; [79] After l-bromo-3-iodobenzene (10 g, 35.35 mmol) and 2-naphthalene bromic acid(5.47 g, 31.82 mmol) were dissolved in anhydrous THF (100 mL), Pd(PPh ) (1.2 g, 1.06 mmol) and 50 mL of 2M K CO aqueous solution were added and then refluxed <n="17"/>for 24 hours. The organic layer was extracted by using ethyl acetate and water was removed with magnesium sulfate. The organic layer was filtered at reduced pressure and concentrated, and the solvent was removed. The resulting substance was purified by using column chromatography and then recrystallized in THF and ethanol to obtain a white solid compound 2a (8.5 g, 85percent).[80] MS [M + H] = 283
76% With sodium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux Under an argon gas atmosphere, 243 g (1.41 mol) of 2-naphthaleneboronic acid, 400 g (1.41 mol) of 3-bromoiodobenzene, 3.27 g (28.2 mmol) of tetrakis(triphenylphosphine)palladium(0), 6.4 L of toluene and 3.2 L of aqueous solution of 2M sodium carbonate were added together, and stirred while being refluxed for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 303 g of 2-(3-bromophenyl)naphthalene was obtained at an yield of 76percent.
Reference: [1] Patent: WO2008/13399, 2008, A1, . Location in patent: Page/Page column 14-15
[2] Patent: US2010/331585, 2010, A1, . Location in patent: Page/Page column 94-95
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 19, p. 4096 - 4114
  • 11
  • [ 108-36-1 ]
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  • [ 667940-23-0 ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate In tetrahydrofuran; water for 24 h; Heating / reflux Example 13 : Preparation of compound 30; [196][197] 13-A. Preparation of compound 13a[198] Under N atmosphere, 1,3-dibromophenyl (10 g, 42.2 mmol), 2-naphthyl boronic acid (5.16 g, 42.2 mmol), and Pd(PPh ) (2.4 g, 2.1 mmol) were added to a 2 M aqueous solution of potassium carbonate (50 mL) and THF (300 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, dried over magnesium sulfate, and distilled under reduced pressure. The resultant was purified by column chromatography to prepare a compound 13a (4.6 g, 47percent). MS [M] = 233
Reference: [1] Patent: WO2007/86695, 2007, A1, . Location in patent: Page/Page column 72
  • 12
  • [ 32316-92-0 ]
  • [ 870774-29-1 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water at 50℃; for 4 h; Inert atmosphere
Stage #2: With hydrogenchloride In water
General procedure: The procedure for entry v is shown as an example: compound 3 (150 mg,0.228 mmol, tetrahydrate), 2-methoxyphenylboronic acid (139 mg,0.912 mmol), K2CO3 (126 mg, 0.912 mmol), and PdCl2(PPh3)2 (19 mg,0.027 mmol) were placed in a flask under a N2 atmosphere. Degassed EtOH/H2O (5/1; 3 mL) was added, and the reaction mixture was stirred at 50 C for4 h. The solvent was removed under reduced pressure. Hexane/EtOAc (1/1)was added, and the residue was extracted with water. To the aqueous layer,1 M HCl was added dropwise until the pH was approximately 2, and theresulting mixture was extracted twice with EtOAc. The combined organiclayers were dried with Na2SO4 and concentrated in vacuo. The residue waspurified by silica gel column chromatography (hexane/EtOAc = 4/1?1/1) togive 51 mg of the biaryl compound (49percent).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 3, p. 720 - 724
  • 13
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  • [ 918655-03-5 ]
Reference: [1] Patent: US2011/245495, 2011, A1,
[2] Patent: WO2012/121561, 2012, A1,
[3] Patent: US2012/267615, 2012, A1,
[4] Patent: KR2017/49296, 2017, A,
[5] Patent: JP6145989, 2017, B2,
  • 14
  • [ 32316-92-0 ]
  • [ 1062555-59-2 ]
Reference: [1] Patent: US2011/152587, 2011, A1,
[2] Patent: WO2013/58137, 2013, A1,
  • 15
  • [ 32316-92-0 ]
  • [ 1092390-02-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 3, p. 1397 - 1401
  • 16
  • [ 5798-76-5 ]
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  • [ 1092390-02-7 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16787 - 16790
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