[ CAS No. 1627917-17-2 ] {[proInfo.proName]}

Name: 1627917-17-2|Naphtho[2,3-b]benzofuran-2-ylboronic acid|97%
Brand: Ambeed
SKU: A581113
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Quality Control of [ 1627917-17-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1627917-17-2 ]

Product Details of [ 1627917-17-2 ]

CAS No. :	1627917-17-2	MDL No. :	MFCD30187284
Formula :	C₁₆H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FGXHNQHUZOHBRS-UHFFFAOYSA-N
M.W :	262.07	Pubchem ID :	90433280
Synonyms :

Safety of [ 1627917-17-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1627917-17-2 ]

* 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 [ 1627917-17-2 ]

[ 1627917-17-2 ] Synthesis Path-Downstream 1~8

1
[ 121-43-7 ]
[ 1627917-16-1 ]
[ 1627917-17-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2-bromobenzo[b]naphtho[2,3-d]furan With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h;	2 Example 2: To a 100 ml three-necked flask was added 2.97 g of 2-bromonaphtho [2,3-b] benzofuran,Anhydrous tetrahydrofuran 50ml,Replacement air, nitrogen protection,Liquid nitrogen ethanol to reduce the temperature to -78 ,Samples of n-butyllithium (2.5 mol / L, 4 ml) were slowly added dropwise,Stirring 2h, re-dropped to -78 slowly dropping trimethyl borate 2.3g,After completion of the dropwise addition, the mixture was stirred at room temperature for 12 h.TLC showed complete reaction,Add water to quench,Rotate the tetrahydrofuran, add 60ml methylene chloride solution,Saturated aqueous sodium sulfite solution, washed with water,Dried over anhydrous sodium sulfate and concentrated to recrystallize to give 2-naphthalene [2,3-b] benzofuran boronic acid as a white solid,Yield 86%.
65%	Stage #1: 2-bromobenzo[b]naphtho[2,3-d]furan With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 5.16667h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 1h;	1.6 Synthesis of intermediate (B) 12.6g of intermediate (A) and 500 mL of tetrahydrofuran (dehydrated) were put in a flask, and the resultantwas cooled to -78°C. 28 mL of n-BuLi (1.60M in hexane) was added, and stirring was conducted for 2 hours whileelevating the temperature to 0°C. Then, the solution was again cooled to -78°C, and 11.6g of B(OMe)3 was added. Afterstirring at 10 minutes at -78°C, stirring was further conducted for 5 hours while gradually elevating the temperature toroom temperature.[0141] After completion of the reaction, 1 N HCl aq. (100 mL) was added, and the reaction solution was stirred at roomtemperature for 1 hour. Then, the solution was transferred to a separating funnel, and extracted with ethyl acetate.[0142] This solution was dried with MgSO4, concentrated and washed with hexane, whereby 7.2g (yield: 65%) of whitesolids of intermediate (B) were obtained.

Reference： [1]Current Patent Assignee: WUHAN SHANGSAI OPTOELECTRONICS TECHNOLOGY CO LTD - CN106883203, 2017, A Location in patent: Paragraph 0061; 0062; 0063
[2]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2924029, 2015, A1 Location in patent: Paragraph 0130; 0140; 0141; 0142

2
[ 1627917-17-2 ]
[ 2236593-32-9 ]
[ 2236590-04-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 65℃; for 18h;	3 5-Bromo-3,9,-dimethyl-10-(naphthalen-1-yl)benzo[G]quinoline (MW: 412.33) of step (3) 32.16 g(0.078 mol), naphtho(2,3-b)benzofuran-2-ylboronic acid (MW: 262.08) 22.53 g (0.086 mol), Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium) MW: 1155.58) 0.9 g, sodium carbonate (MW: 106) 9.92 g, toluene 250 mL, ethanol 50 mL, water50mL was placed in a 500mL reaction flask, inserted into a condenser tube, thermometer, stirred reaction, heated to 65 ° C, reaction for 18h, to be reactedAfter the bundle is cooled, 150 mL of ethanol is added, and then filtered, washed with water, and dried to obtain3,9-Dimethyl-10-(naphthalen-1yl)-5-(naphtho[2,3-b]benzofuran-2-yl)benzo[G]quinoline(MW: 549.21) 36.84 g (0.067 mol), which is the compound (57), yield86%.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN108164462, 2018, A Location in patent: Paragraph 0081; 0083; 0086

3
[ 1627917-17-2 ]
[ 2236593-34-1 ]
[ 2236591-91-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With C₃₉H₂₅N; sodium carbonate In ethanol; water; toluene at 65℃; for 18h;	6 Step (3)of5-bromo-10-(naphthalen-1-yl)benzo[G]quinoline (MW: 383.29) 29.89 g (0.078 mol),Naphtho(2,3-b)benzofuran-2-ylboronic acid(MW: 262.08) 22.53g (0.086mol), Pd(PPh3)4 (tetrakis(triphenylphosphine)Palladium) (MW: 1155.58) 0.9 g, sodium carbonate (MW: 106) 9.92 g, toluene 250 mL, ethanol 50 mL, water 50 mL placed in 500 mL antiIn the bottle, insert a condenser tube, a thermometer, stir the reaction, heat up to 65 ° C, react for 18 h, cool down after the reaction is over, add150mL ethanol, filtered, washed, dried,10-(naphthalen-1yl)-5-(naphtho[2,3-b]benzofuran-2-yl)benzo[G]quinoline (MW: 549.21) 36.84 g (0.067 mol), ie Compound (57a), yield 86%.

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN108164462, 2018, A Location in patent: Paragraph 0107; 0112

4
[ 1627917-17-2 ]
[ 1195975-03-1 ]
[ 2414552-70-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere;	2 Example 2: Preparation of Compound No. 9 Add raw material A-2 (7.79 g, 16 mmol), raw material B-2 (4.63 g, 17.6 mmol), and potassium carbonate (6.64 g, 48.1 mmol) to the reaction vessel. Replace the reaction vessel with nitrogen, and add tetrahydrofuran (90 mL) under a nitrogen atmosphere. ), Water (90 mL), nitrogen replaced the reactor, and stirred well. Tetrakis (triphenylphosphine) palladium (0.37 g, 0.32 mmol) was added under a nitrogen atmosphere, and the reaction was completed at 80 ° C. The reaction was monitored by TLC. The reaction produced a solid which was filtered under suction under reduced pressure. The obtained solid residue was purified by column chromatography to obtain compound 9 (8.2 g) with a yield of 82% and a mass spectrum detection value of 622.72.

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN110330472, 2019, A Location in patent: Paragraph 0051-0053

5
[ 1627917-17-2 ]
[ 2396655-79-9 ]
[ 2404669-76-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	Compound 1-Bromo-3-chlorotriphenylene (10 g, 29.41 mmol), naphtho [2,3-b] benzofuran-2-yl boronic acid (7.7 g, 29.41 mmol) and tetrakis triphenylforce 4 mol% of pinpalladium (Tetrakis (triphenylphosphine) palladium) was added to 60 ml of tetrahydrofuran, and potassium carbonate (12.2 g, 88.23 mmol) was dissolved in 30 ml of water.After stirring for 12 hours at 80 ° C. the reaction was terminated and cooled to room temperature to separate the water and the organic layer.Anhydrous magnesium sulfate was added only to the organic layer, stirred, filtered through a silica pad, concentrated under reduced pressure, and purified by column to obtain 10.5 g of intermediate 5-1 (yield 75%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2019/141598, 2019, A Location in patent: Paragraph 0227; 0228

6
[ 121848-75-7 ]
benzo[b]naphtho[2,3-d]furan-2-ylboronic acid [ No CAS ]
C₄₄H₂₅BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-dicyclophosphine-2',6'-dimethoxybiphenyl; sodium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;	1 Synthesis of Intermediate A 8.2g (16.0mmol) of a mixture of 10,10'-dibromo-9,9'-bianthracene, 5.0g (19.1mmol) naphtho[2,3-b]benzofuran-2-ylboronic acid,0.4g (0.3mmol) of tetrakis(triphenylphosphine) palladium (Pd(PPh3)4), 0.2g (0.6mmol) of 2-bicyclic phosphine-2',6'-dimethoxybiphenyl (2 -Dicyclophosphine-2',6'-dimethoxy-biphenyl), 2.5g (24.0mmole) of sodium carbonate (Na2CO3),A mixture of 120 ml of toluene (Tol), 40 ml of ethanol (EtOH) and 12 ml of water was placed under nitrogen, and then heated at 80° C. for 16 hours with stirring.After the reaction was completed, the mixture was cooled to room temperature.The solution was extracted with 100 ml ethyl acetate (3 times) followed by 300 ml water.The organic layer was dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure.The residue was purified by silica gel column chromatography to obtain a white solid product (7.8 g, 75%).

Reference： [1]Current Patent Assignee: LUMINESCENCE TECHNOLOGY CORPORATION - CN111434658, 2020, A Location in patent: Paragraph 0104-0107

7
[ 1627917-17-2 ]
[ 1526983-08-3 ]
[ 2562332-38-9 ]

Yield	Reaction Conditions	Operation in experiment
85.14%	Stage #1: benzo[b]naphtho[2,3-d]furan-2-ylboronic acid; C₄₉H₃₄BrN In 1,4-dioxane; water at 50℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water Reflux;	2 Under the protection of N2, add the G-5 (20.0g, 27.90mmol) obtained in the above reaction and the raw material H-5 (7.31g, 27.90mmol) to 200ml of dioxane/pure water (volume ratio 3/1) In the mixed solution, after stirring at 50°C for 15 minutes, potassium carbonate (7.71g, 55.80mmol),Tetratriphenylphosphine palladium (0.34g, 0.3mmol), after the addition, heat to reflux,After the reaction is complete, the concentrated product after suction filtration is subjected to 200ml dichloromethane/petroleum ether (v:v=1:10) mixed solution column chromatography, and then recrystallized from toluene solution.Compound 5 (20.28 g, yield: 85.14%, Mw: 854.21) was obtained.

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111808055, 2020, A Location in patent: Paragraph 0096; 0103-0104

8
[ 1627917-17-2 ]
[ 1456703-10-8 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
86.87%	Stage #1: benzo[b]naphtho[2,3-d]furan-2-ylboronic acid; C₃₅H₂₅BrN₂ In 1,4-dioxane; water at 50℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water Inert atmosphere; Reflux;	5 Add G-25 (17.00g, 30.71mmol) and raw material H-25 (8.05g, 30.71mmol) obtained in the above reaction to 170ml of dioxane/pure water (volume ratio 3/1) mixture,After stirring at 50°C for 15 min, potassium carbonate (8.49g, 61.42mmol),Tetratriphenylphosphine palladium (0.36g, 0.31mmol), after the addition, heat to reflux, wait until the reaction is complete,After suction filtration, the concentrated product was subjected to 160ml dichloromethane/petroleum ether (v:v=1:10) mixed solution column chromatography, and then recrystallized from toluene solution to finally obtain compound 25(18.42g, yield: 86.87%, Mw: 690.72).

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111808055, 2020, A Location in patent: Paragraph 0123; 0130-0131

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[ 1627917-17-2 ]

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1627917-17-2 ] {[proInfo.proName]}

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[ 1627917-17-2 ] Synthesis Path-Downstream 1~8

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Organoboron

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