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4-(Dibenzofuranyl)boronic acid

4-(Dibenzofuranyl)boronic acid

4-(Dibenzofuranyl)boronic acid

CAS No.: 100124-06-9

Category Products

Cat.NO.:A265658 Purity:98%

Product Details of [ 100124-06-9 ]

CAS No. :	100124-06-9
Formula :	C₁₂H₉BO₃
M.W :	212.01
SMILES Code :	OB(C1=C2OC3=CC=CC=C3C2=CC=C1)O
MDL No. :	MFCD00092336
InChI Key :	ZXHUJRZYLRVVNP-UHFFFAOYSA-N
Pubchem ID :	2734328

Safety of [ 100124-06-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 100124-06-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	13
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	63.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.02
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.79
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.31
Solubility	0.104 mg/ml ; 0.000491 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.34
Solubility	0.0961 mg/ml ; 0.000453 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.86
Solubility	0.0293 mg/ml ; 0.000138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.77 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12’782’590 molecules and tested on 40 external molecules (r² = 0.94)	2.96

Application In Synthesis of [ 100124-06-9 ]

* 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 [ 100124-06-9 ]

[ 100124-06-9 ] Synthesis Path-Downstream 1~13

1
[ 1920-66-7 ]
[ 100124-06-9 ]
4-amino-5-nitro-2-(4-dibenzofuran)pyrimidine [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1859 – 1867.

2
[ 100124-06-9 ]
[ 2620-76-0 ]
[ 1312212-67-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 90℃; for 4.5h;Inert atmosphere;	[Example 5] This example will give descriptions of a method of synthesizing 2-[4-(dibenzofuran-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBFBIm-II) represented by the following Structural formula (130). [Show Image] [Synthesis of 2-[4-(dibenzofuran-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBFBIm-II)] The synthesis scheme of 2-[4-(dibenzofuran-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBFBIm-II) is illustrated in (B-5). [Show Image] In a 100-mL three-neck flask, a mixture of 1.7 g (5.0 mmol) of <strong>[2620-76-0]2-(4-bromophenyl)-1-phenyl-1H-benzimidazole</strong>, 1.0 g (5.0 mmol) of dibenzofuran-4-boronic acid, 22 mg (0.1 mmol) of palladium(II) acetate, 60 mg (0.2 mmol) of tri(ortho-tolyl)phosphine, 30 mL of toluene, 3 mL of ethanol, and 7.5 mL of a 2 mol/L aqueous solution of potassium carbonate was stirred to be degassed under reduced pressure. Then, the mixture was heated and stirred at 90 C for 4.5 hours under a nitrogen stream. After a predetermined time, 50 mL of toluene was added to this mixture solution, and the organic layer of the resulting suspension was suction filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The resulting filtrate was concentrated, followed by purification using silica gel column chromatography. The chromatography was carried out using a mixed solvent of toluene and ethyl acetate in a ratio of 19 to 1 as a developing solvent. The obtained fractions were concentrated, and hexane was added to the mixture, followed by irradiation with ultrasonic waves. The precipitated solid was collected by suction filtration. Thus, 2.0 g of a white powder was obtained in 92% yield, which was the substance to be produced. The Rf values of the produced substance and <strong>[2620-76-0]2-(4-bromophenyl)-1-phenyl-1H-benzimidazole</strong> were respectively 0.10 and 0.22, which were found by silica gel thin layer chromatography (TLC) (with a developing solvent containing ethyl acetate to hexane in a ratio of 1 to 10). A nuclear magnetic resonance (NMR) method identified this compound as 2-[4-(dibenzofuran-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: DBFBIm-II), which was the substance to be produced. 1H NMR data of the obtained substance are as follows: 1H NMR (CDCl3, 300 MHz): δ (ppm) = 7.27-7.63 (m, 13H), 7.74-7.78 (m, 2H), 7.89-8.00 (m, 5H). FIGS. 21A and 21B illustrate the 1H NMR charts. Note that FIG. 21B is a chart showing an enlarged part of FIG. 21 A in the range of 7.0 ppm to 8.5 ppm. Further, FIG. 22A shows an absorption spectrum of a toluene solution of DBFBIm-II, and FIG. 22B shows an emission spectrum thereof. FIG. 23A shows an absorption spectrum of a thin film of DBFBIm-II, and FIG. 23B shows an emission spectrum thereof. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-550, produced by JASCO Corporation). The measurements were performed with samples prepared in such a manner that the solution was put in a quartz cell while the thin film was obtained by evaporation onto a quartz substrate. The absorption spectrum of the solution was obtained by subtracting the absorption spectra of quartz and toluene from those of quartz and the solution, and the absorption spectrum of the thin film was obtained by subtracting the absorption spectrum of a quartz substrate from those of the quartz substrate and the thin film. In FIGS. 22A and 22B and FIGS. 23A and 23B, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). In the case of the toluene solution, an absorption peak was observed at around 323 nm, and emission wavelength peaks were 365 nm, 385 nm and 405 nm (excitation wavelength: 329 nm). In the case of the thin film, absorption peaks were observed at around 300 nm and 324 nm, and an emission wavelength peak was 405 nm (excitation wavelength: 330 nm).

References: [1]Patent: EP2354135,2011,A1 .Location in patent: Page/Page column 56-57.

3
[ 1698-16-4 ]
[ 100124-06-9 ]
[ 1365549-03-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux;	200mL of tetrahydrofuran is introduced into the compound B-1 and diphenyl 14.8g (50mmol) prepared in Synthesis Example 5 and [b, d] furan-4-yl boronic acid (12.7g, 60mmol), followed by Pd (PPh3) 4 (2.89g, 2.5mmol) and 100mL2MK2CO3 aqueous solution, the resulting mixture was stirred for 12 hours while refluxing. The temperature was cooled to normal temperature and distilled water was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) was dried, then the solvent was removed, and subjected to silica gel column chromatography to give 16.1g (42mmol, 84%) Compound E-1.
78%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 15h;	Preparation of Compound 8-1 [206] Compound 7-1 (10 g, 33.8 mmol), dibenzo[b,d]furan-4-ylboronic acid (8.6 g, 40.56 mmol), Pd(PPh3)4 (2 g, 1.7mmol), K2CO3 (34 g, 321 mmol), toluene 60mL, EtOH 12mL and purified water 12mL were mixed and then stirred at 120C for 15 hours. After termination of the reaction, the resultant mixture was allowed to stand and the water layer was removed, after which the organic layer was concentrated. Silica column purification was then carried out, yielding Compound 8-1 (10.2 g, 78%).

References: [1]Patent: CN105601621,2016,A .Location in patent: Paragraph 0324; 0325; 0326.
[2]Patent: WO2012/36482,2012,A1 .Location in patent: Page/Page column 34.

4
[ 100124-06-9 ]
[ 6163-58-2 ]
[ 57103-20-5 ]
[ 1364890-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In methanol; ethanol; hexane; water; acetone; toluene;	Synthesis Method of 3,6-di(dibenzofuran-4-yl)-9-phenyl-9H-carbazole (abbreviated as DBF2PC-II)To a 200-mL three-neck flask were added 2.0 g (5.0 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>, 3.2 g (11 mmol) of dibenzofuran-4-boronic acid, 10 mg (0.1 mmol) of palladium(II) acetate, 30 mg (0.1 mmol) of tris(o-tolyl)phosphine, 50 mL of toluene, 5 mL of ethanol, and 7.5 mL of a 2 mol/L aqueous potassium carbonate solution.This mixture was degassed while being stirred under reduced pressure, and then heated and stirred at 90° C. for 6.5 hours under a nitrogen stream to be reacted.After the reaction, 250 mL of toluene was added to this reaction mixture and the mixture was heated.The mixture was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135) in this order to give a filtrate.The resulting filtrate was purified by silica gel column chromatography (a developing solvent in which the toluene/hexane ratio was 1:3).The obtained fraction was concentrated, acetone, methanol, and water were added thereto, and the mixture was irradiated with ultrasonic waves.Then, acetone and methanol were added to the obtained precipitate and the mixture was irradiated with ultrasonic waves, filtrated, washed, and dried.Thereby, 2.8 g of a target substance, white powder, was obtained in 69percent yield.A reaction scheme of the above synthesis method is illustrated in the following (E-1).The Rf values of the white powder obtained through the reaction and <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> were respectively 0.32 and 0.55, which were found by silica gel thin layer chromatography (TLC) (a developing solvent in which the ethyl acetate/hexane ratio was 1:10).The white powder obtained by the step 1 was subjected to nuclear magnetic resonance (NMR) spectroscopy.The measurement data are shown below.show the 1H NMR charts.Note that is an enlarged chart of .By the measurement results, it was confirmed that the white powder obtained by the step 1 was DBF2PC-II, which is represented by the structural formula (208).1H NMR (CDCl3, 300 M Hz): delta (ppm)=7.37 (dt, J=7.8 Hz, J=1.2 Hz, 2H), 7.44-7.56 (m, 5H), 7.60-7.69 (m, 8H), 7.75 (dd, J=7.2 Hz, J=1.5 Hz, 2H), 7.95 (dd, J=7.8 Hz, J=1.5 Hz, 2H), 8.00-8.04 (m, 4H), 8.75 (d, J=1.5 Hz, 2H).

References: [1]Patent: US2012/91887,2012,A1 .

5
[ 38557-72-1 ]
[ 100124-06-9 ]
3,5-Dimethyl-2-(dibenzofuran-4-yl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium carbonate;bis(triphenylphosphine)palladium(II) dichloride; In water; acetonitrile;	Step 1: Synthesis of 3,5-Dimethyl-2-(dibenzofuran-4-yl)pyrazine (abbreviation: Hdm4 dbfpr) First, into a recovery flask equipped with a reflux pipe were placed 1.51 g of <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong>, 2.25 g of 4-dibenzofuranylboronic acid, 1.12 g of sodium carbonate, 0.048 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air inside the flask was replaced with argon. Heating was performed by microwave irradiation (2.45 GHz, 100 W) of this reaction container for 10 minutes, so that reaction occurred. After that, water was added to this reaction solution, and extraction with dichloromethane was carried out. A solution of the obtained extract was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. After the solvent of this solution was distilled, the obtained residue was washed with methanol, so that the pyrazine derivative which was the object of the synthesis, Hdm4 dbfpr, was obtained (a pale orange powder in a yield of 65%). Note that a microwave synthesis system (Discover, produced by CEM Corporation) was used for the microwave irradiation. The synthesis scheme of Step 1 is illustrated in the following scheme (x-1).

References: [1]Patent: US2012/104373,2012,A1 .

6
[ 100124-06-9 ]
[ 109179-31-9 ]
C₂₀H₁₄O₂ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 3550 – 3553.

7
[ 100124-06-9 ]
[ 57381-62-1 ]
C₂₀H₁₃ClO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux;	(4-Dibenzofuranyl) boronic acid ((4-dibenzofuranyl) boronic acid), 30 g (141.5 mmol), <strong>[57381-62-1]methyl-2-bromo-4-chlorobenzoate</strong> (methyl-2-bromo-5-chlorobenzoate), 37.1 g ( 148.6 mmol), tetrakistriphenylphosphine palladium 8.2 g (7.1 mmol) dissolved in toluene 550 ml was added to flask placed in a nitrogen atmosphere. Potassium carbonate (potassium carbonate) 104.2 g (707.51 mmol) was dissolved in 550 ml toluene, and the aqueous solution 353.8 ml was stirred under reflux for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, dried with magnesium sulfite (magnesium sulphate), filtered and the filtrate was concentrated under reduced pressure. The resulting mixture was purified by silica gel column chromatography using n-hexane / dichloromethane (7:3 volume ratio) to give the desired compound of intermediate (D) 38.2 g (80percent yield) as a white solid.
71%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 21h;Inert atmosphere;	50 g (200 mmol) of methyl-2-bromo-5-c Details Products CAS 50-81-7 Read more Products CAS 56-35-9 Read more Products CAS 87595-03-7 Read more Reviews There are no reviews yet. Be the first to review “4-(Dibenzofuranyl)boronic acid” 取消回复您的邮箱地址不会被公开。必填项已用 * 标注 Your rating * Your review * Name * Email * 在此浏览器中保存我的显示名称、邮箱地址和网站地址，以便下次评论时使用。 Previous (S)-3-Amino-2-(4-chlorophenyl)propanoic acid Next 1-Nitro-4-vinylbenzene Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.