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Quality Control of [ 1421789-04-9 ]

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Product Details of [ 1421789-04-9 ]

CAS No. :	1421789-04-9	MDL No. :	MFCD32215031
Formula :	C₂₅H₁₇BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RDUYDKNCVPJOAG-UHFFFAOYSA-N
M.W :	360.21	Pubchem ID :	71249378
Synonyms :

Safety of [ 1421789-04-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1421789-04-9 ]

* 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 [ 1421789-04-9 ]

[ 1421789-04-9 ] Synthesis Path-Downstream 1~12

1
[ 5419-55-6 ]
[ 1361227-58-8 ]
9,9’-spirobi[9H-fluorene]-3-boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium; In tetrahydrofuran; at -78℃;Inert atmosphere; Schlenk technique;	In a 200 mL Schlenk reaction flask,Under argon protection,Three-bromo-9,9'-spirobifluorene 2.0 g (5.05 mmol) and 80 mL of tetrahydrofuran were added.After cooling,2.4M n-butyl was added dropwise at -78CLithium 2.2mL (5.28mmol),Stirring is completed for 1 hour,1.42 g (7.57 mmol) of triisopropyl borate was added dropwise.After stirring for 1 hour,Automatic warming,The reaction was overnight.Add 20mL of ammonium chloride solution,Quenching reaction.Transfer the reaction material to a jarAfter the solvent is distilled off under reduced pressure,Add 80 mL of dichloromethane and 80 mL of water to the bottle,DissolvedWashed,Layered,The aqueous layer was extracted twice with 15 mL of dichloromethane.Combine the organic phase,Then wash twice with 80mL water,To neutrality.Divide the water layer,Organic layer plus 15g anhydrous sodium sulfate,Dry for 3 hours.Evaporate the solvent under reduced pressureWhite solid 1.46g,Yield 80%.MS (EI): m/z 360.16 [M+].elementAnalysis calculated for C25H17BO2 (%): C 83.36, H 4.76; Found: C 83.41, H 4.84.

Reference： [1]Patent: CN107141191,2017,A .Location in patent: Paragraph 0092; 0093; 0096

2
[ 1421789-04-9 ]
[ 2213454-54-5 ]
[ 2213453-93-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 3h;	6.1 [Embodiment 6] compound 46 synthesis of Step1: reaction vessel Riga 1 - 1 (3.40 g, 8.4 mmol), 9, 9 - fluorene -3 - boric acid (3.31 g, 9.2 mmol), four-triphenylphosphine palladium (0.7 g, 1 . 08 mmol), potassium carbonate (5.3 g, 38.3 mmol), toluene 60 ml, ethanol 20 ml, and distilled water 20 ml, in the 120 °C is stirred under the condition 3 h. After the end of the distilled water to stop the reaction of the reaction, ethyl acetate extraction. The organic layer using MgSO4 drying. For removing the solvent is distilled under reduced pressure after silica gel column purification to obtain compound 46 (3.67 g, 68%).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN107805242, 2018, A Location in patent: Paragraph 0076-0078

3
[ 1421789-04-9 ]
[ 2416790-14-0 ]
[ 2433899-37-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	6 Synthesis of Compound II-1-35 A 1 liter three-necked flask equipped with magnetic stirring, after nitrogen replacement, sodium carbonate 40.07g (0.378mol), 9,9'-spirobifluorene-3boronic acid 75.6g (purity 99%, 0.21mol) and toluene 100ml were added in sequence.After nitrogen replacement again, 0.5 g of Pd132 was added in sequence.After the addition is complete, heat to 80 ° C.Start to add dropwise a solution consisting of 44.0 g of compound P1 (purity 99%, 0.1 mol) and 100 ml of toluene, and the temperature is controlled at 75-90 ° C.Cool to room temperature, add 100ml of deionized water to hydrolyze, stir for 10 minutes, filter, filter cake repeatedly boiled with DMF several times to obtain 72.8g of light yellow solid, purity 99%, yield 80%.

Reference： [1]Current Patent Assignee: BEIJING YUNJI TECHNOLOGY CO LTD (YUNJI PHOTONICS) - CN110903296, 2020, A Location in patent: Paragraph 0108-0114

4
[ 1421789-04-9 ]
[ 2415915-01-2 ]
[ 2415914-92-8 ]

Yield	Reaction Conditions	Operation in experiment
82.69%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere;	3 Synthesis Example 3: Synthesis of Compound 2-4 4-Biphenyl-3-yl-6-(4-bromo-phenyl)-2-p-tolyl-pyrimidine (4.32 g, 12 mmole) with Spiro-9,9′-bifluorene-2-boronic acid (4.78 g, 10 mmole) and potassium carbonate (6.73) g, 35 mmole) was placed in a reaction flask. 34 ml of toluene, 10 ml of ethanol, 14 ml of deionized water were then added therein, and the reaction flask was placed in an oil bath, connecting to nitrogen and a condenser. Then, heating and stirring was initiated to 80° C. At the same time, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.58 g, 0.5 mmole) was added to the reaction flask. When the reaction was completed and solids were precipitated, the oil bath was removed, and the mixture was cooled before being filtered. The filtered cake was further added with 100 ml of deionized water. After stirring for 10 minutes, it was filtered again. The filter cake was added to 250 ml of tetrahydrofuran, and the mixture was heated and stirred until it was completely dissolved. Then, the mixture was added to a column packed with 20 g of silica gel, purified by chromatography, and concentrated to a white solid. After washing with ethyl acetate, filtered again and dried, a white solid (about 5.9 g) was obtained with a yield of 82.69%. 1H NMR (CDCl3, 400 MHz), δ8.64 (d, 2H), 8.50 (t, 1H), 8.42 (d, 2H), 8.18 (t, 1H), 8.14 (d, 1H), 8.09 (s, 1H), 7.95 (d, 1H), 7.85-7.89 (m, 4H), 7.78 (t, 1H), 7.72-7.74 (m, 2H), 7.65 (t, 1H), 7.53 (t, 2H), 7.35-7.44 (m, 7H), 7.13-7.17 (m, 3H), 6.85 (d, 1H), 6.77-6.82 (m, 3H), 2.47 (s, 3H).

Reference： [1]Current Patent Assignee: E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD. - US2020/127211, 2020, A1 Location in patent: Paragraph 0071-0073

5
[ 1073062-42-6 ]
9,9’-spirobi[9H-fluorene]-3-boronic acid [ No CAS ]
C₄₆H₂₈ClN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.46%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 76℃; for 5h; Inert atmosphere;	Synthesis of Compound 6 Intermediate II-B-1 (5.5g, 13.01mmol), 9,9'-spirobis [9H-fluorene] -2-boronic acid (4.80g, 13.27mmol), tetrakis (triphenylphosphine) palladium (0.75 g, 0.65 mmol), potassium carbonate (3.59 g, 26.02 mmol), tetrabutylammonium chloride (0.18 g, 0.65 mmol), toluene (44 mL), ethanol (22 mL) and deionized water (11 mL) were added to the three-necked flask The temperature was raised to 76 ° C under nitrogen protection, heated to reflux and stirred for 5h. After the reaction, the solution was cooled to room temperature. After the reaction, the solution was cooled to room temperature. The reaction solution was washed with water and then dried with magnesium sulfate. After filtration, the filtrate was passed through a short silica gel column and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtained Intermediate II-F (6.99, yield 81.46%).

Reference： [1]Current Patent Assignee: SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO.,LTD - CN111039881, 2020, A Location in patent: Paragraph 0099-0101

6
[ 1421789-04-9 ]
[ 2417745-00-5 ]
[ 2417745-04-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	6 Synthesis of Compound II-1-32 1 liter three-necked bottle with magnetic stirring,Add sodium carbonate in sequence after replacing with nitrogen40.07g (0.378mol), 9,9’-spirobifluorene-3-boronic acid 75.6g (purity 99%, 0.21mol)And toluene 100ml. After nitrogen replacement again, 0.5 g of Pd132 was added in sequence. After the addition,Heated to 80 . Start dropping the compound P1 (purity 99%, 0.1mol) from 56.6gA solution consisting of 100ml of toluene, controlled temperature 75-90 . Cool to room temperature,Add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter,The filter cake was repeatedly boiled and washed with DMF several times, and filtered to obtain 80.81g of light yellow solid,The purity is 99% and the yield is 78%.

Reference： [1]Current Patent Assignee: BEIJING YUNJI TECHNOLOGY CO LTD (YUNJI PHOTONICS) - CN111087407, 2020, A Location in patent: Paragraph 0110-0116

7
[ 1421789-04-9 ]
[ 2603482-23-9 ]
[ 2603482-04-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 120℃; for 24h; Inert atmosphere;	7 Example 7 Compound M10 Weigh precursor 3 (5mmol), (12mmol),Dissolve with a mixed solvent of toluene and ethanol with a volume ratio of 2:1;In an inert atmosphere,Then add Na2CO3 aqueous solution and catalyst Pd(PPh3)4 (0.6mmol);React the mixed solution of the above reactants at a reaction temperature of 120°C for 24 hours,The reaction solution was cooled and filtered, and the filtrate was rotary evaporated and passed through a silica gel column to obtain the target product M10.The yield is about 75%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112321629, 2021, A Location in patent: Paragraph 0105-0108

8
[ 1421789-04-9 ]
[ 2639774-22-2 ]
[ 2639771-97-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 110℃; for 16h; Inert atmosphere;	26 Under argon atmosphere, add 9-2 (11.9g, 35.0mmol) in a 250mL two-necked flask,3,6-Di-tert-butylcarbazole (9.8 g, 35.0 mmol), cesium carbonate (22.8 g, 70.0 mmol) and anhydrous DMF (80 mL) were heated to 120° C. and stirred for 6 hours.After the reaction was cooled to room temperature, the reaction solution was settled in saturated brine, the solid was filtered out, washed with deionized water, and dried under reduced pressure at 80°C. The crude product was separated by column to obtain the product 9-3 (18.5g, yield: 88 %).

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN112592362, 2021, A Location in patent: Paragraph 0446; 0450-0453

9
[ 1421789-04-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos In tetrahydrofuran; water at 80℃; for 10h; Inert atmosphere;	11 Synthesis Example 11: Synthesis of Chemical 10 Weigh 1.63g (5.0mmol, 1.0eq) of Intermediate 2d,1.84g (5.1mmol, 1.05eq) of 9,9'-spirobifluorene-3-boronic acid,0.09g (0.10mmol, 0.02eq) of tris(dibenzylideneacetone)dipalladium,0.18g (0.40mmol, 0.08eq) 2-dicyclohexylphosphorus-2,4,6-triisopropylbiphenyl,2.1g (10.0mmol, 2.0eq) tripotassium phosphate, add 30ml tetrahydrofuran and 5ml deionized water, under nitrogen protection, react at 80°C for 10h.The reaction was stopped, cooled to room temperature, poured into 100 ml of water, and extracted with dichloromethane three times. The organic phase was collected, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation.Dichloromethane/methanol was recrystallized, filtered, and dried to obtain 2.49 g of yellow solid with a yield of 82%.

Reference： [1]Current Patent Assignee: ZHEJIANG HONGWU TECHNOLOGY CO LTD - CN113105491, 2021, A Location in patent: Paragraph 0074-0076

10
[ 1421789-04-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;	20 Synthesis of compound 414 Under an argon atmosphere, 46.2 g (100 mmol) of 2,7-dibromophenanthro[4,5-abc]phenazine was added to the reaction vessel,9,9'-spirobi[fluorene]-3-ylboronic acid 36.0g (100mmol),[1,3-Bis(2,6-Di-isopropylphenyl)-4,5-dihydroimidazol-2-ylidene]chloro][3-phenylallyl]palladium(II) catalyst 648 mg, 200ml (300mmol) of 1.5M sodium carbonate aqueous solution and 1000ml of ethylene glycol dimethyl ether (DME), heated at 80°C and stirred overnight. After cooling to room temperature, 500 ml of water was added, the solid was separated out, filtered, the obtained solid was washed with ethanol, and 400 ml of toluene was recrystallized to obtain 56.9 g of compound 414 with a yield of 79% and an HPLC purity of 99.1%.

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113429399, 2021, A Location in patent: Paragraph 0229-0233

11
[ 1421789-04-9 ]
[ 2713521-45-8 ]
[ 2713521-46-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;	2 Synthesis of compound 21 Under argon atmosphere, add 31.6g (100mmol) of 1-bromo-4-chloropyrene to the reactor,3-boronic acid-9,9'-spirobifluorene 36.0g (100mmol),Tetrakis(triphenylphosphine)palladium 1.16g (1.0mmol), 1.5M sodium carbonate aqueous solution 200ml (300mmol) and ethylene glycol dimethyl ether 800ml (DME), heated at 80°C and stirred overnight. After cooling to room temperature, adding 500ml of water, the solid precipitated out, filtered, and the obtained solid was washed with ethanol.38.6 g of 3-(4-chloropyrene-1-yl)-9,9'-spirocyclo[fluorene] was obtained, with a yield of 70% and an HPLC purity of 98.9%.

Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN113429399, 2021, A Location in patent: Paragraph 0098-0102

12
[ 1421789-04-9 ]
[ 53348-05-3 ]
[ 2766739-83-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 95℃; for 24h; Inert atmosphere;	1.S1 The compound represented by formula (3) (0.72 g, 2 mmol), Compound (2.1mmol, 0.77g) shown in formula (2), tetrakistriphenylphosphine palladium (0.1mmol, 0.11g), potassium carbonate (4mmol, 0.55g) were added to 100 milliliters of there-necked flasks,Then add 60 ml of toluene/ethanol/water (3:1:2), Heated to 95°C for 24 hours under nitrogen, cooled to room temperature, the crude product was concentrated and purified by silica gel column chromatography to obtain 660 mg of yellow product with a yield of 55%.
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU); GUANGDONG INDUSTRIAL UNIV - CN114292264, 2022, A Location in patent: Paragraph 0051; 0053-0056
[2]Chen, Jia-Xiong; Wang, Hui; Xiao, Ya-Fang; Wang, Kai; Zheng, Ming-Hui; Chen, Wen-Cheng; Zhou, Lu; Hu, Dehua; Huo, Yanping; Lee, Chun-Sing; Zhang, Xiao-Hong [Small, 2022, vol. 18, # 21]

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H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 1421789-04-9 ] {[proInfo.proName]}

Quality Control of [ 1421789-04-9 ]

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[ 1421789-04-9 ] Synthesis Path-Downstream 1~12

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