641144-16-3|(10-Bromoanthracen-9-yl)boronic acid| Ambeed

CAS No. :	641144-16-3
Formula :	C₁₄H₁₀BBrO₂
M.W :	300.94
SMILES Code :	OB(C1=C2C=CC=CC2=C(Br)C3=CC=CC=C13)O
MDL No. :	MFCD06411293
InChI Key :	FAVOIVPFJSKYBE-UHFFFAOYSA-N
Pubchem ID :	16217487

Safety of [ 641144-16-3 ]

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

Application In Synthesis of [ 641144-16-3 ]

* 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 [ 641144-16-3 ]

[ 641144-16-3 ] Synthesis Path-Downstream 1~54

1
[ 641144-16-3 ]
[ 214958-27-7 ]
2-[4-(10-bromo-anthracen-9-yl)-phenyl]-imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux;	Ten point six grams (33 mmol) of 2-(4-iodophenyl)-imidazo [1,2-a] pyridine, 10 g (33 mmol) of <strong>[641144-16-3]10-bromoanthracene-9-boronic acid</strong> and 0.77 g of tetrakis (triphenylphosphine) palladium were dissolved into 100 milliliter of 1,2-dimethoxyethane, and adding 50 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 11.7 g of 2-[4-(10-bromo-anthracene-9-yl)-phenyl]-imidazo [1,2-a] pyridine (yield: 78 %).

References: [1]Patent: EP1582516,2005,A1 .Location in patent: Page/Page column 83.

3
[ 121-43-7 ]
[ 523-27-3 ]
[ 641144-16-3 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1201 - 1207.

4
C₁₆H₁₄BBrO₂ [ No CAS ]
[ 641144-16-3 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1201 - 1207.

5
[ 641144-16-3 ]
C₁₄H₈BrN₃ [ No CAS ]

References: [1]Synthesis,2009,p. 1506 - 1512.

6
[ 641144-16-3 ]
[ 35356-70-8 ]
[ 1227732-28-6 ]
[ 121848-75-7 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2655 - 2656.

7
[ 641144-16-3 ]
[ 35356-70-8 ]
[ 1227732-29-7 ]
[ 121848-75-7 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2655 - 2656.

8
[ 641144-16-3 ]
[ 319906-42-8 ]
[ 1314357-51-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 18h;Inert atmosphere; Reflux;	A mixture of 2-iodo-9,9-bis-n-hexylfluorene (1.28 g, 2.79 mmol), 9-bromoanthracen-10-boronic acid (0.84 g, 2.79 mmol), Pd(PPh3)4 (0.065 g, 0.12 mmol) and 2 M Na2CO3 (8 ml) aqueous solution in THF (12 ml) was degassed with N2 for 5 min. The reaction mixture was stirred at reflux under N2 for 18 h. After being cooled to room temperature, water (50 ml) was added and extracted with CH2Cl2 (50 ml×2). The combined organic phase was washed with water (50 ml), brine solution (50 ml), dried over anhydrous Na2SO4, filtered, and the solvents were removed to dryness. Purification by column chromatography over silica gel eluting with a mixture of CH2Cl2 and hexane (1:4) followed by recrystallization from a mixture of CH2Cl2 and methanol afforded the 9-bromo-10-(9,9-dihexylfluoren-2-yl) anthracene 6 (0.66 g, 52%) as a light yellow solid, mp 158 C; numax (KBr) 2928, 1462, 1438, 1344, 1260, 1020, 890 cm-1; deltaH (300 MHz, CDCl3) 0.76-0.88 (10H, m), 1.09-1.14 (12H, m), 1.95-2.01 (4H, m), 7.34-7.40 (7H, m), 7.59 (2H, t, J=8.8 Hz), 7.72 (2H, d, J=9.0 Hz), 7.81 (1H, dd, J=3.3, 2.7 Hz), 7.89 (1H, d, J=7.5 Hz), 8.62 (2H, d, J=8.7 Hz); deltaC (75 Hz, CDCl3) 13.99, 22.47, 23.85, 29.60, 31.52, 40.37, 55.26, 119.62, 119.83, 122.92, 124.87, 125.46, 125.91, 126.54, 126.92, 127.32, 127.44, 129.73, 130.30, 131.20, 136.90, 140.81, and 150.95; HRMS (ESI): [MH+] found 589.3042. C39H42Br requires 589.2432.

References: [1]Chemical Communications,2011,vol. 47,p. 7122 - 7124.
[2]Tetrahedron,2012,vol. 68,p. 1853 - 1861.
[3]European Journal of Organic Chemistry,2013,p. 3825 - 3834.

9
[ 641144-16-3 ]
[ 278176-05-9 ]
[ 736138-39-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 20h;Inert atmosphere; Reflux;	A mixture of 2,7-diiodo-9,9-bis-n-hexylfluorene (1.11 g, 1.90 mmol), 9-bromoanthracen-10-boronic acid (1.20 g, 3.99 mmol), Pd(PPh3)4 (0.11 g, 0.10 mmol), and 2 M Na2CO3 (10 ml) aqueous solution in THF (15 ml) was degassed with N2 for 5 min. The reaction mixture was stirred at reflux under N2 for 20 h. After being cooled to room temperature, water (50 ml) was added and extracted with CH2Cl2 (50 ml×2). The combined organic phase was washed with water (50 ml), brine solution (50 ml), dried over anhydrous Na2SO4, filtered, and the solvents were removed to dryness. Purification by column chromatography over silica gel eluting with a mixture of CH2Cl2 and hexane (1:4) followed by recrystallization from a mixture of CH2Cl2 and methanol afforded the 2,7-bis(9-bromoanthracene-10-yl)-9,9-dihexylfluorene 9 (0.90 g, 56%) as a light yellow solid, mp 188 C; numax (KBr) 2927, 1460, 1440, 1340, 1261, 1020, 893 cm-1; deltaH (300 MHz, CDCl3) 0.8 (6H, t, J=6.9 Hz), 0.94 (4H, m), 1.14-1.27 (12H, m), 2.04 (4H, t, J=7.8 Hz), 7.40-7.48 (8H, m), 7.65 (4H, t, J=8.4 Hz), 7.79 (4H, d, J=9.0 Hz), 8.04 (2H, d, J=8.1 Hz), 8.66 (4H, d, J=9.0 Hz); deltaC (75 Hz, CDCl3) 14.02, 22.40, 24.06, 29.55, 31.57, 40.34, 55.51, 119.86, 122.70, 125.56, 126.04, 126.97, 127.40, 127.95, 130.01, 130.34, 131.21, 137.32, 138.229, 140.53,151.21; HRMS (ESI): [MH+] found 843.8920. C53H49Br2 requires 843.2193.

References: [1]Chemical Communications,2011,vol. 47,p. 7122 - 7124.
[2]Tetrahedron,2012,vol. 68,p. 1853 - 1861.

10
[ 641144-16-3 ]
[ 854045-93-5 ]
[ 1408316-17-5 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 13274 - 13276.

11
[ 641144-16-3 ]
[ 1312108-97-6 ]
[ 1408316-31-3 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 13274 - 13276.

12
[ 641144-16-3 ]
[ 1446436-48-1 ]

References: [1]European Journal of Organic Chemistry,2013,p. 3825 - 3834.

13
[ 641144-16-3 ]
[ 1355580-45-8 ]

References: [1]European Journal of Organic Chemistry,2013,p. 3825 - 3834.

14
[ 641144-16-3 ]
[ 1314357-49-7 ]

References: [1]European Journal of Organic Chemistry,2013,p. 3825 - 3834.

15
[ 641144-16-3 ]
[ 121848-75-7 ]

Yield	Reaction Conditions	Operation in experiment
41%	With Cu(OH)x has been encapsulated over montmorillonite-KSF; air; In methanol; at 20℃; for 1h;Green chemistry;	General procedure: To a solution of arylboronic acid (1 mmol) in methanol (0.5 ml),clay encapsulated Cu(OH)x(6 mg) was added and this heterogeneous mixture was vigorously stirred at ambient temperature for 30-120 min. After completion of reaction (monitored by TLC), the reaction mixture was filtered to separate the catalyst. Solvent of the filtrate was removed under reduced pressure and then worked up in hexane:water (1:1) system. The aqueous phase was isolated and back extracted with hexane. The combined organic layer was dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to afford the desired product. The prepared products were characterized NMR and mass spectral analysis. The spectral data and physical properties thus obtained were compared with data reported in literature [references herein]. NMR spectrawere recorded on Brucker-Advance DPX FT-NMR 400 MHz instru-ment. ESI-MS and HRMS spectra were recorded on Agilent 1100 LC and HRMS-6540-UHD machines. Melting points were recordedon digital melting point apparatus. IR spectra were recorded onPerkin-Elmer IR spectrophotometer.

References: [1]Applied Catalysis A: General,2014,vol. 470,p. 232 - 238.

16
[ 641144-16-3 ]
[ 1567365-75-6 ]
[ 1567365-76-7 ]

References: [1]RSC Advances,2014,vol. 4,p. 6752 - 6760.

17
[ 641144-16-3 ]
[ 2569-57-5 ]
2-(2-(10-bromoanthracen-9-yl)-2-phenylhydrazinyl)pyridine [ No CAS ]

References: [1]Inorganic Chemistry,2014,vol. 53,p. 12002 - 12013.

18
[ 641144-16-3 ]
[ 1564-64-3 ]

References: [1]RSC Advances,2014,vol. 4,p. 55305 - 55312.

19
[ 641144-16-3 ]
[ 515-03-7 ]
15-(10-bromoanthracen-9-yl)-sclareol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3432 - 3444.

20
[ 641144-16-3 ]
[ 23038-36-0 ]
C₂₆H₁₇BrO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		1-bromo- naphthalene 2.07 g (10 mmol) was dissolved in 30 mL THF , 4 mL of n -butyllithium at -78 ( 2.5M inHexane) was added. After an hour at the same temperature, 22-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2.0 mL (10 mmol) was added . After stirring for 5 hours at room temperature water was added and three times with diethyl ether (30 mL)Washed . After drying the washed diethyl ether layer over MgSO4 followed by drying under reduced pressure the product was obtained and then purified by silica gel columnPurification by intermediate I-1 1.96 g ( yield 77 %) was obtained by chromatography . And the resulting compound is confirmed by LC-MS

References: [1]Patent: KR2015/127023,2015,A .Location in patent: Paragraph 0396; 0537; 0538; 0539; 0540; 0541.

21
[ 641144-16-3 ]
[ 589-87-7 ]
9-bromo-10-(4-bromophenyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 5h;	1.46 g (5.09 mmol) of 2,6-dibromonaphthalene, 0.75 g (2.99 mmol) of (6-bromonaphthalene-2-yl) boronic acid, 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), and 0.62 g (4.48 mmol) of K2CO3 were dissolved in 60 ml of a mixed solution of THF/H2O (a volume ratio of 2/1) to prepare a reaction solution, followed by stirring the reaction solution at a temperature of 70 C. for 5 hours. After cooling the reaction solution to room temperature, 40 ml of water was added to the reaction solution and extracted the reaction solution three times with 50 ml of diethyl ether to collect organic layers. The collected organic layers were dried with magnesium sulfate and a solvent was evaporated therefrom to obtain residues. The obtained residues were isolated and purified by using silica gel column chromatography to obtain 0.91 g of Intermediate 39-A (yield 74%).

References: [1]Patent: KR2015/22288,2015,A .Location in patent: Paragraph 0224; 0228; 0229; 0230.

22
[ 641144-16-3 ]
9-bromo-7,7-dimethyl-7H-benzo[c]fluorine [ No CAS ]
C₃₃H₂₃Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.08%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; at 70 - 80℃;Inert atmosphere;	Under a nitrogen atmosphere, 35.42 g (0.11 mol) of compound A was added to a 500 mL three-necked flask,Potassium carbonate 41.4 g, water 96.6 g, toluene 250 g,Pd(PPh3)4 1.15g, open the stir, the use of oil bath heating,When the temperature rose to 70-80 C began to drop C solution of tetrahydrofuran(30.1 g of compound B solution in 90.3 g of tetrahydrofuran)Dropping 6-8h, TLC detection reaction is complete, after layering, washing, solvent removal of crude products, add the product theoretical weight and other weight of toluene and ethanol to get the compound C, Dried at 95 C to give 35.5 g of compound C in a yield of 71.08%.

References: [1]Patent: CN106831448,2017,A .Location in patent: Paragraph 0045; 0046; 0047; 0048.

23
[ 641144-16-3 ]
2-bromo-11,11-dimethyl-11H-benzo[b]fluorene [ No CAS ]
C₃₃H₂₃Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.7%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; at 70 - 80℃;Inert atmosphere;	Under nitrogen protection, To a 500 mL three-necked flask was added 35.42 g (0.11 mol) of compound B, 41.4 g of potassium carbonate, Water 96.6g, toluene 250g, Pd(PPh3)4 1.15g, open stirring, the use of oil bath heating, Start when the temperature rises to 70-80 C A solution of C in tetrahydrofuran (30.1 g of compound B solution, 90.3 g of tetrahydrofuran) was added dropwise and incubated for 6-8 h,TLC detection reaction is complete, after stratification, washing, solvent removal of the crude product, add the product theoretical weight and other weight of toluene and ethanol to get the crystallizationCompound C was dried at 95 C to give 38.8 g of compound C in a yield of 77.7%.

References: [1]Patent: CN106831448,2017,A .Location in patent: Paragraph 0045; 0046; 0051; 0052.

24
[ 641144-16-3 ]
C₄₅H₃₃N [ No CAS ]