[ CAS No. 365564-05-2 ] {[proInfo.proName]}

Name: 365564-05-2|1,3,5-Tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene|97%
Brand: Ambeed
SKU: A188038
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Quality Control of [ 365564-05-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 365564-05-2 ]

SDS Specification

Alternatived Products of [ 365564-05-2 ]

Product Details of [ 365564-05-2 ]

CAS No. :	365564-05-2	MDL No. :	MFCD17167305
Formula :	C₂₄H₃₉B₃O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VKOLBYNBPONPAE-UHFFFAOYSA-N
M.W :	456.00	Pubchem ID :	56776718
Synonyms :

Calculated chemistry of [ 365564-05-2 ]

Physicochemical Properties

Num. heavy atoms :	33
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.75
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	135.87
TPSA :	55.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.88
Log Po/w (WLOGP) :	2.58
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	1.87
Consensus Log Po/w :	2.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.68
Solubility :	0.000957 mg/ml ; 0.0000021 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.78
Solubility :	0.00076 mg/ml ; 0.00000167 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.06
Solubility :	0.0000394 mg/ml ; 0.0000000863 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.51

Safety of [ 365564-05-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 365564-05-2 ]

* 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.

Upstream synthesis route of [ 365564-05-2 ]
Downstream synthetic route of [ 365564-05-2 ]

[ 365564-05-2 ] Synthesis Path-Upstream 1~13

1
[ 25015-63-8 ]
[ 71-43-2 ]
[ 99770-93-1 ]
[ 24388-23-6 ]
[ 196212-27-8 ]
[ 365564-05-2 ]

Reference： [1] Organic letters, 2001, vol. 3, # 18, p. 2831 - 2833

2
[ 626-39-1 ]
[ 25015-63-8 ]
[ 24388-23-6 ]
[ 196212-27-8 ]
[ 365564-05-2 ]
[ 594823-67-3 ]
[ 408492-26-2 ]

Reference： [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901

3
[ 626-39-1 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24 h; Inert atmosphere	Synthesis of Compound 1: Anhydrous DMF (10 mL) was purged with N2 and then transferred via a cannula into a three-neck round bottomed flask charged with 1, 3, 5-tribromobenzene (1.00 g, 3.17 mmol) and bis (pinacolato) diboron (2.54 g, 9.53 mmol) . Potassium acetate (1.87 g, 19.0 mmol) and Pd(dppf)Cl₂ (0.087 g, 0.12 mmol) were then quickly added into the flask. The resulting mixture was stirred vigorously and heated at 90 °C for 24 hours. After cooling down to room temperature, deionized water (120 mL) was added. Black precipitate was collected by filtration, and washed with deionized water three times, which was dried under vacuum (98percent yield) .
88%	With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere	A mixture of 1,3,5-tribromobenzene (7.96 g, 25.3 mmol), bis(pinacolato)diboron (21.2 g, 83.5 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium (2.78 g, 3.79 mmol), potassium acetate (22.3 g, 228 mmol) in anhydrous 1,4-dioxane (400 mL) was degassed for 80 minutes. Mixture was then heated to 80° C. overnight under argon. After cooling to room temperature, the remaining solids were filtered off. The filtrate was dried under vacuum, redissolved in methylene chloride (400 mL) then washed with water (2.x.300 mL) and brine (300 mL). Organic layer was dried over sodium sulfate and loaded onto silica gel. A silica plug (11percent ethyl acetate in hexanes) and precipitation from methylene chloride/methanol gave 4 (9.76 g, 88percent yield).
71.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 85℃; for 24 h; Inert atmosphere	Under a nitrogen atmosphere, 250ml three-necked flask 1,3,5-bromobenzene (15.74g, 50mmol), United pinacolato ester (41.9g, 0.165mol, TCI), potassium acetate (48.58g, 0.495mol), 1,1'- bis (diphenylphosphino) ferrocene palladium dichloride (4.08g, 5mmol) and dimethylformamide (300ml), 85 The reaction mixture was stirred under heating 24h.After completion of the reaction naturally cooled, the reaction solution was extracted with ethyl acetate, washed with saturated brine three times, the resulting organic layer was dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate was removed under reduced pressure to remove the solvent.Separated by column chromatography, the mobile phase was chloroform.After the spin-dry vacuum dried to give a white powder 16.25g, yield 71.3percent.

69%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Schlenk technique; Inert atmosphere	10108] In a flame-dried Schlenk tube under argon atmosphere, 1,3,5-tribromobenzene (200 mg, 0.64 mmol) and S2Pin2 (731.3 mg, 2.88 mmol) were dissolved in 20 ml 1,4-dioxane. Flame dried KOAc (471.1 mg, 4.8 mmol) was added quickly to the mixture followed by PdC12 (dppf) (15.5 mg, 0.029 mmol). The mixture was heated at 90° C. overnight. The progress of reaction was tracked by TLC (9 hexanes: 1 ethyl acetate) and visualization was achieved in an iodine chambet Two spots (Rf 0.20 and RI 0.25) were observed and heating was stopped and allowed to cool down to room temperature. 20-30 ml ethyl acetate was added to quench the reaction. 30 ml DI water was added to extract the aqueous phase and 30 ml brine (2x) was used to wash the organic phase, dried over anhydrous MgSO4 and filtered. After concentrating down the filtrate, hexanes: ethyl acetate (9:1) mixture was used to elute Rf 0.25 in silica column chromatography to yield white powder [6 9percent, 200 mgI. 1R NMR (300.0 MHz, CDC13): ö 8.36 (s, 3R; CR), ö 1.32 (s, 36R; CR3). 13C {1R} NMR (75.5 MRz, CDC13): ö144.14 (CR), ö 83.79 (CCR3), ö 24.96 (CR3), n.o. (CS).
57%	With potassium acetate In dimethyl sulfoxide at 80℃; for 20 h; Inert atmosphere	EXAMPLE 1 <Synthesis of 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6)> 8.6 g of 1,3,5-tribromobenzene, 25.0 g of bis(pinacolato)diboron, 24.1 g of potassium acetate, 250 ml of dimethyl sulfoxide previously dewatered with Molecular Sieves 4A, and 1.4 g of PdCl₂(dppf)-CH₂Cl₂ were put into a nitrogen-purged reactor, then heated, and stirred at 80°C for 20 hours. After cooled to room temperature, the reaction liquid was put into 1000 ml of water, and stirred for 30 minutes. The precipitate was collected through filtration, and the precipitate was washed with methanol to obtain a crude product. The crude product was dissolved in 200 ml of ethyl acetate, the insoluble matter was removed through filtration, and the filtrated was concentrated to dryness to obtain 7.1 g (yield 57percent) of a white powder, 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene. 2.5 g of the obtained 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene, 3.8 g of 6-bromo-[2,2']-bipyridine, 32.3 ml of aqueous 1 M potassium carbonate solution, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 108 ml of toluene and 27 ml of ethanol were put into a nitrogen-purged reactor, and heated under reflux with stirring for 18 hours. After cooled to room temperature, this was processed for liquid-liquid separation with 100 ml of water and 100 ml of toluene added thereto, and the organic layer was further washed with 100 ml of water. The organic layer was dewatered with anhydrous magnesium sulfate and then concentrated to obtain a crude product. The crude product was purified through column chromatography (carrier: NH silica gel, eluent: chloroform/n-hexane) to obtain 1.1 g (yield 38percent) of a white powder, 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6).

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2641 - 2650
[2] Patent: WO2015/157239, 2015, A1, . Location in patent: Paragraph 00121; 00122
[3] Patent: US2011/196158, 2011, A1, . Location in patent: Page/Page column 7; 8
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 15, p. 3431 - 3439
[5] Patent: CN103396355, 2016, B, . Location in patent: Paragraph 0062-0064
[6] Patent: US2016/178766, 2016, A1, . Location in patent: Paragraph 0106; 0107; 0108
[7] Chemical Communications, 2018, vol. 54, # 68, p. 9529 - 9532
[8] Chemical Communications, 2018, vol. 54, # 70, p. 9745 - 9748
[9] Patent: EP2269987, 2011, A1, . Location in patent: Page/Page column 29-30
[10] Organic Electronics: physics, materials, applications, 2010, vol. 11, # 12, p. 1966 - 1973
[11] New Journal of Chemistry, 2015, vol. 39, # 11, p. 8771 - 8779
[12] Chemical Communications, 2012, vol. 48, # 75, p. 9370 - 9372

4
[ 372-38-3 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1] ACS Catalysis, 2017, vol. 7, # 7, p. 4535 - 4541

5
[ 108-70-3 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1] ChemCatChem, 2016, vol. 8, # 14, p. 2317 - 2320

6
[ 123-91-1 ]
[ 626-39-1 ]
[ 365564-05-2 ]

Reference： [1] Patent: US2015/364699, 2015, A1,
[2] Patent: US2015/364699, 2015, A1,

7
[ 73183-34-3 ]
[ 71-43-2 ]
[ 365564-05-2 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 37, p. 15169 - 15172

8
[ 25015-63-8 ]
[ 71-43-2 ]
[ 99770-93-1 ]
[ 24388-23-6 ]
[ 196212-27-8 ]
[ 365564-05-2 ]

Reference： [1] Organic letters, 2001, vol. 3, # 18, p. 2831 - 2833

9
[ 347389-74-6 ]
[ 365564-05-2 ]

Reference： [1] Chemistry - A European Journal, 2007, vol. 13, # 19, p. 5408 - 5425
[2] European Journal of Organic Chemistry, 2011, # 18, p. 3283 - 3292

10
[ 99770-93-1 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 37, p. 15169 - 15172

11
[ 408492-28-4 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8408 - 8411

12
[ 626-39-1 ]
[ 25015-63-8 ]
[ 24388-23-6 ]
[ 196212-27-8 ]
[ 365564-05-2 ]
[ 594823-67-3 ]
[ 408492-26-2 ]

Reference： [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901

13
[ 626-39-1 ]
[ 25015-63-8 ]
[ 24388-23-6 ]
[ 196212-27-8 ]
[ 365564-05-2 ]
[ 594823-67-3 ]
[ 408492-26-2 ]

Reference： [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901

[ 365564-05-2 ] Synthesis Path-Downstream 1~88

1
[ 347389-74-6 ]
2,2’,2”-(benzene-1,2,4-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
[ 365564-05-2 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 5408 - 5425
[2]European Journal of Organic Chemistry,2011,p. 3283 - 3292

2
zinc 5-(3'-iodophenyl)-10,15,20-tris(3'',5''-di-tert-butylphenyl)porphyrin [ No CAS ]
[ 365564-05-2 ]
C₂₁₀H₂₂₈N₁₂^(6-)*3Zn⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 1085 - 1087

3
[ 884660-31-5 ]
[ 365564-05-2 ]
C₆H₃(C₆H₄ZnC₂₀H₈N₄(C₆H₃(C(CH₃)3)2)3)3 [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 1085 - 1087

4
[ 1138337-70-8 ]
[ 365564-05-2 ]
[ 1138337-69-5 ]

Reference： [1]New Journal of Chemistry,2009,vol. 33,p. 264 - 270

5
[ 626-39-1 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃; for 24h;Inert atmosphere;	Synthesis of Compound 1: Anhydrous DMF (10 mL) was purged with N2 and then transferred via a cannula into a three-neck round bottomed flask charged with 1, 3, 5-tribromobenzene (1.00 g, 3.17 mmol) and bis (pinacolato) diboron (2.54 g, 9.53 mmol) . Potassium acetate (1.87 g, 19.0 mmol) and Pd(dppf)Cl2 (0.087 g, 0.12 mmol) were then quickly added into the flask. The resulting mixture was stirred vigorously and heated at 90 C for 24 hours. After cooling down to room temperature, deionized water (120 mL) was added. Black precipitate was collected by filtration, and washed with deionized water three times, which was dried under vacuum (98% yield) .
88%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;Inert atmosphere;	A mixture of 1,3,5-tribromobenzene (7.96 g, 25.3 mmol), bis(pinacolato)diboron (21.2 g, 83.5 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium (2.78 g, 3.79 mmol), potassium acetate (22.3 g, 228 mmol) in anhydrous 1,4-dioxane (400 mL) was degassed for 80 minutes. Mixture was then heated to 80 C. overnight under argon. After cooling to room temperature, the remaining solids were filtered off. The filtrate was dried under vacuum, redissolved in methylene chloride (400 mL) then washed with water (2×300 mL) and brine (300 mL). Organic layer was dried over sodium sulfate and loaded onto silica gel. A silica plug (11% ethyl acetate in hexanes) and precipitation from methylene chloride/methanol gave 4 (9.76 g, 88% yield).
71.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 85℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 250ml three-necked flask 1,3,5-bromobenzene (15.74g, 50mmol), United pinacolato ester (41.9g, 0.165mol, TCI), potassium acetate (48.58g, 0.495mol), 1,1'- bis (diphenylphosphino) ferrocene palladium dichloride (4.08g, 5mmol) and dimethylformamide (300ml), 85 The reaction mixture was stirred under heating 24h.After completion of the reaction naturally cooled, the reaction solution was extracted with ethyl acetate, washed with saturated brine three times, the resulting organic layer was dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate was removed under reduced pressure to remove the solvent.Separated by column chromatography, the mobile phase was chloroform.After the spin-dry vacuum dried to give a white powder 16.25g, yield 71.3%.

69%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃;Schlenk technique; Inert atmosphere;	10108] In a flame-dried Schlenk tube under argon atmosphere, 1,3,5-tribromobenzene (200 mg, 0.64 mmol) and S2Pin2 (731.3 mg, 2.88 mmol) were dissolved in 20 ml 1,4-dioxane. Flame dried KOAc (471.1 mg, 4.8 mmol) was added quickly to the mixture followed by PdC12 (dppf) (15.5 mg, 0.029 mmol). The mixture was heated at 90 C. overnight. The progress of reaction was tracked by TLC (9 hexanes: 1 ethyl acetate) and visualization was achieved in an iodine chambet Two spots (Rf 0.20 and RI 0.25) were observed and heating was stopped and allowed to cool down to room temperature. 20-30 ml ethyl acetate was added to quench the reaction. 30 ml DI water was added to extract the aqueous phase and 30 ml brine (2x) was used to wash the organic phase, dried over anhydrous MgSO4 and filtered. After concentrating down the filtrate, hexanes: ethyl acetate (9:1) mixture was used to elute Rf 0.25 in silica column chromatography to yield white powder [6 9%, 200 mgI. 1R NMR (300.0 MHz, CDC13): oe 8.36 (s, 3R; CR), oe 1.32 (s, 36R; CR3). 13C {1R} NMR (75.5 MRz, CDC13): oe144.14 (CR), oe 83.79 (CCR3), oe 24.96 (CR3), n.o. (CS).
57%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 20h;Inert atmosphere;	EXAMPLE 1 <Synthesis of 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6)> 8.6 g of 1,3,5-tribromobenzene, 25.0 g of bis(pinacolato)diboron, 24.1 g of potassium acetate, 250 ml of dimethyl sulfoxide previously dewatered with Molecular Sieves 4A, and 1.4 g of PdCl2(dppf)-CH2Cl2 were put into a nitrogen-purged reactor, then heated, and stirred at 80C for 20 hours. After cooled to room temperature, the reaction liquid was put into 1000 ml of water, and stirred for 30 minutes. The precipitate was collected through filtration, and the precipitate was washed with methanol to obtain a crude product. The crude product was dissolved in 200 ml of ethyl acetate, the insoluble matter was removed through filtration, and the filtrated was concentrated to dryness to obtain 7.1 g (yield 57%) of a white powder, 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene. 2.5 g of the obtained 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene, 3.8 g of 6-bromo-[2,2']-bipyridine, 32.3 ml of aqueous 1 M potassium carbonate solution, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 108 ml of toluene and 27 ml of ethanol were put into a nitrogen-purged reactor, and heated under reflux with stirring for 18 hours. After cooled to room temperature, this was processed for liquid-liquid separation with 100 ml of water and 100 ml of toluene added thereto, and the organic layer was further washed with 100 ml of water. The organic layer was dewatered with anhydrous magnesium sulfate and then concentrated to obtain a crude product. The crude product was purified through column chromatography (carrier: NH silica gel, eluent: chloroform/n-hexane) to obtain 1.1 g (yield 38%) of a white powder, 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6).

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650
[2]Patent: WO2015/157239,2015,A1 .Location in patent: Paragraph 00121; 00122
[3]Patent: US2011/196158,2011,A1 .Location in patent: Page/Page column 7; 8
[4]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 3431 - 3439
[5]Patent: CN103396355,2016,B .Location in patent: Paragraph 0062-0064
[6]Patent: US2016/178766,2016,A1 .Location in patent: Paragraph 0106; 0107; 0108
[7]Chemical Communications,2018,vol. 54,p. 9529 - 9532
[8]Chemical Communications,2018,vol. 54,p. 9745 - 9748
[9]Patent: EP2269987,2011,A1 .Location in patent: Page/Page column 29-30
[10]Organic electronics,2010,vol. 11,p. 1966 - 1973
[11]European Journal of Organic Chemistry,2019,vol. 2019,p. 7635 - 7643
[12]Journal of the American Chemical Society,2019,vol. 141,p. 10621 - 10625
[13]Journal of Polymer Science, Part A: Polymer Chemistry,2019,vol. 57,p. 1748 - 1755
[14]New Journal of Chemistry,2015,vol. 39,p. 8771 - 8779
[15]Chemical Communications,2012,vol. 48,p. 9370 - 9372

6
[ 10495-73-5 ]
[ 365564-05-2 ]
[ 1026024-63-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 18h;Inert atmosphere;	EXAMPLE 1 <Synthesis of 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6)> 8.6 g of 1,3,5-tribromobenzene, 25.0 g of bis(pinacolato)diboron, 24.1 g of potassium acetate, 250 ml of dimethyl sulfoxide previously dewatered with Molecular Sieves 4A, and 1.4 g of PdCl2(dppf)-CH2Cl2 were put into a nitrogen-purged reactor, then heated, and stirred at 80C for 20 hours. After cooled to room temperature, the reaction liquid was put into 1000 ml of water, and stirred for 30 minutes. The precipitate was collected through filtration, and the precipitate was washed with methanol to obtain a crude product. The crude product was dissolved in 200 ml of ethyl acetate, the insoluble matter was removed through filtration, and the filtrated was concentrated to dryness to obtain 7.1 g (yield 57%) of a white powder, 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene. 2.5 g of the obtained 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene, 3.8 g of 6-bromo-[2,2']-bipyridine, 32.3 ml of aqueous 1 M potassium carbonate solution, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 108 ml of toluene and 27 ml of ethanol were put into a nitrogen-purged reactor, and heated under reflux with stirring for 18 hours. After cooled to room temperature, this was processed for liquid-liquid separation with 100 ml of water and 100 ml of toluene added thereto, and the organic layer was further washed with 100 ml of water. The organic layer was dewatered with anhydrous magnesium sulfate and then concentrated to obtain a crude product. The crude product was purified through column chromatography (carrier: NH silica gel, eluent: chloroform/n-hexane) to obtain 1.1 g (yield 38%) of a white powder, 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6).

Reference： [1]Organic electronics,2010,vol. 11,p. 1966 - 1973
[2]Patent: EP2269987,2011,A1 .Location in patent: Page/Page column 29-30

7
[ 100366-68-5 ]
[ 365564-05-2 ]
[ 1185738-82-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 18h;Inert atmosphere; Reflux;	EXAMPLE 4 <Synthesis of 1,3,5-tris(2,2';6',2"-terpyridin-6-yl)benzene (compound 29)> 3.0 g of 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene obtained in the above-mentioned Example 1, 6.2 g of 6-bromo-[2,2';6',2"]-terpyridine, 59.2 ml of aqueous 1 M potassium carbonate solution, 0.39 g of tetrakis(triphenylphosphine)palladium(0), 131 ml of toluene and 33 ml of ethanol were put into a nitrogen-purged reactor, and heated under reflux with stirring for 18 hours. After cooled to room temperature, this was processed for liquid-liquid separation with 100 ml of water and 100 ml of toluene added thereto, and the organic layer was further washed with 100 ml of water. The organic layer was dewatered with anhydrous magnesium sulfate and then concentrated to obtain a crude product. The crude product was purified through column chromatography (carrier: NH silica gel, eluent: chloroform/n-hexane) to obtain 1.8 g (yield 35%) of a white powder, 1,3,5-tris(2,2';6',2"-terpyridin-6-yl)benzene (compound 29). The structure of the obtained white powder was identified through NMR. The 1H-NMR data are shown in Fig. 4. In the 1H-NMR (CDCl3), the following 33 hydrogen signals were detected: d (ppm) = 9.09 (3H), 8.83 (3H), 8.74 (3H), 8.70 (6H), 8.51 (3H), 8.06 (9H), 7.90 (3H), 7.37 (3H).

Reference： [1]Organic electronics,2010,vol. 11,p. 1966 - 1973
[2]Patent: EP2269987,2011,A1 .Location in patent: Page/Page column 30

8
[ 365564-05-2 ]
tripotassium benzene-1,3,5-tris-(trifluoroborate) [ No CAS ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,2010,vol. 66,p. m152-m156

9
[ 3437-95-4 ]
[ 365564-05-2 ]
[ 15509-95-2 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3283 - 3292

10
[ 591-50-4 ]
[ 365564-05-2 ]
[ 612-71-5 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3283 - 3292

11
[ 696-62-8 ]
[ 365564-05-2 ]
[ 7509-20-8 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3283 - 3292

12
[ 402-43-7 ]
[ 365564-05-2 ]
[ 753014-99-2 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3283 - 3292

13
[ 619-44-3 ]
[ 365564-05-2 ]
[ 117100-41-1 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 3283 - 3292

14
[ 1160274-30-5 ]
[ 365564-05-2 ]
[ 1325731-86-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃;	A mixture of <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (4) (456 mg, 1.0 mmol), 2-(5-bromopyridin-3-yl)benzo[d]oxazole (822 mg, 3.0 mmol), Pd(PPh3)4 (180 mg, 0.16 mmol) and K2CO3 (828 mg, 6.0 mmol) in 1,4-dioxane (30 mL) and water (6 mL) was degassed, then heated at 90 C. overnight. A light yellow precipitate was filtered and washed with methanol to give an off white solid (ET-1) (0.62 g, 95% yield).

Reference： [1]Patent: US2011/196158,2011,A1 .Location in patent: Page/Page column 7; 9

15
[ 99586-31-9 ]
[ 365564-05-2 ]
[ 1325731-87-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 95℃;Inert atmosphere;	A mixture of <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (4) (1.824 g, 4.0 mmol), 2-(3-bromophenyl)benzo[d]oxazole (5) (3.28 g, 12 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) and K2CO3 (3.31 g, 24 mmol) in 1,4-dioxane (100 mL) and water (20 mL) was degassed then heated at 95 C. under argon overnight. After cooled to room temperature, filtration and washing with methanol gave a white solid (ET-2) (2.62 g, quantitative yield).

Reference： [1]Patent: US2011/196158,2011,A1 .Location in patent: Page/Page column 7; 9

16
[ 19654-14-9 ]
[ 365564-05-2 ]
[ 1325731-88-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃;Inert atmosphere;	A mixture of <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (4) (500 mg, 1.14 mmol), 2-(3-bromophenyl)benzo[d]thiazole (7) (1.15 g, 3.98 mmol), tetrakis(triphenylphosphine)palladium (140 mg, 0.12 mmol), sodium carbonate (1.51 g, 14.2 mmol), THF (25 mL), and water (14 mL) was degassed for 25 minutes. The mixture was heated at reflux (80 C.) overnight under argon. After cooling, the mixture was poured into ethyl acetate (125 mL) then washed with saturated sodium bicarbonate solution (100 mL), water (100 mL), and brine (100 mL). A flash column (gradient of 5 to 10% acetone in hexanes) and precipitation from methylene chloride/methanol gave 611 mg of material (ET-3) in 76% yield.

Reference： [1]Patent: US2011/196158,2011,A1 .Location in patent: Page/Page column 9; 10-11

17
[ 1325731-89-2 ]
[ 365564-05-2 ]
[ 1325731-90-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 85℃;Inert atmosphere;	A mixture of 2-(5-bromopyridin-3-yl)benzo[d]thiazole (8) (4.0 g, 13.7 mmol), <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (4) (1.83 g, 4.16 mmol), tetrakis(triphenylphosphine)palladium (474 mg, 0.411 mmol), sodium carbonate (5.18 g, 48.9 mmol), THF (100 mL), and water (60 mL) was degassed for 20 minutes. The mixture was heated at reflux (85 C.) overnight under argon. After cooling to room temperature, the reaction mixture was placed into a separatory funnel and the aqueous layer was removed. The organic phase (containing solids) was then filtered and washed with water, methanol, acetone and THF. Remaining solids were dried to give 2.70 g of product (ET-4) in 92% yield.

Reference： [1]Patent: US2011/196158,2011,A1 .Location in patent: Page/Page column 11; 12

18
[ 365564-05-2 ]
C₆H₁₂B₃^(3-)*3Li⁽¹⁺⁾ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 5414 - 5421

19
[ 365564-05-2 ]
4C₄H₈O*C₆H₁₂B₃^(3-)*3Li⁽¹⁺⁾ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 5414 - 5421

20
[ 109-99-9 ]
[ 16853-85-3 ]
[ 365564-05-2 ]
3Li⁽¹⁺⁾*C₆H₃(BH₃)3^(3-)*0.33C₄H₈O=Li₃(C₆H₃(BH₃)3)*0.33C₄H₈O [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 5414 - 5421

21
[ 365564-05-2 ]
[ 1397264-17-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9370 - 9372
[2]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650
[3]Patent: WO2015/157239,2015,A1

22
[ 365564-05-2 ]
[ 1397264-18-4 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9370 - 9372

23
[ 365564-05-2 ]
C₃₀H₂₄O₉ [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9370 - 9372

24
[ 148490-97-5 ]
[ 365564-05-2 ]
[ 1397264-16-2 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9370 - 9372

25
[ 99770-93-1 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 15169 - 15172

26
[ 73183-34-3 ]
[ 71-43-2 ]
[ 365564-05-2 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 15169 - 15172

27
C₂₂H₂₆Br₂O₄ [ No CAS ]
[ 365564-05-2 ]
C₇₂H₈₁Br₃O₁₂ [ No CAS ]

Reference： [1]Chemical Science,2013,vol. 4,p. 84 - 88
[2]Journal of the American Chemical Society,2014,vol. 136,p. 16452 - 16458

28
[ 69249-61-2 ]
[ 365564-05-2 ]
C₄₅H₇₂S₃Sn₃ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2407 - 2416

29
[ 69249-61-2 ]
[ 365564-05-2 ]
1,3,5-tris(3-hexylthiophen-2-yl)benzene [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2407 - 2416

30
[ 365564-05-2 ]
[ 161299-90-7 ]

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2407 - 2416

31
[ 1003-09-4 ]
[ 365564-05-2 ]
[ 15509-95-2 ]

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2407 - 2416

32
[ 31181-90-5 ]
[ 365564-05-2 ]
[ 1482413-54-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 17999 - 18006
[2]Chemistry - A European Journal,2019,vol. 25,p. 5472 - 5479

33
[ 365564-05-2 ]
benzene-1,3,5-triyltriboronic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 1516 - 1520
Angew. Chem.,2014,vol. 126,p. 1542 - 1546,5
[2]RSC Advances,2018,vol. 8,p. 3803 - 3808
[3]Chemical Communications,2018,vol. 54,p. 9529 - 9532

34
C₆₆H₆₄BrN₅O₃ [ No CAS ]
[ 365564-05-2 ]
C₂₀₄H₁₉₅N₁₅O₉ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 10439 - 10449

35
[ 1609557-97-2 ]
[ 365564-05-2 ]
[ 1609557-98-3 ]

Yield	Reaction Conditions	Operation in experiment
27%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 24h;Inert atmosphere; Reflux;	A mixture of <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (0.20 g, 0.44 mmol), compound 2 (0.78 g, 1.71 mmol), and K2CO3 (0.60 g, 4.4 mmol) in distilled water (20 mL) and toluene (20 mL) was charged and bubbled by nitrogen for 15 min, then Pd(PPh3)4 (20 mg) was added. The mixture was refluxed for 24 h under nitrogen. After cooling to room temperature, the mixture was extracted with dichloromethane for three times. Then the organic phase was combined and dried over anhydrous Na2SO4. Removing the solvent under reduced press, the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, v/v=3/1) to give a light yellow oil (0.14g). Yield: 27%. 1H NMR (500 MHz, CDCl3, ppm): delta 8.85 (d, J=1.5 Hz, 3H), 8.58 (d, J=1.5 Hz, 3H), 8.18-8.16 (m, 3H), 8.06 (s, 3H), 8.01-7.99 (m, 3H), 7.59 (d, J=8.5 Hz, 3H), 7.46 (d, J=8.5 Hz, 3H), 4.39 (t, J=7,7 Hz, 6H), 2.74 (s, 9H), 1.97-1.92 (m, 6H), 1.44-1.24 (m, 54H), 0.86 (t, J=6.5, 7.5 Hz, 9H) (Fig.S7). 13C NMR (100 MHz, CDCl3, ppm): delta 197.6, 143.6, 142.9, 140.8, 133.6, 128.9, 126.5, 126.2, 124.9, 123.8, 122.7, 122.1, 119.3, 109.6, 108.5, 53.4, 43.5, 31.9, 29.5, 29.4, 29.3, 29.0, 27.3, 26.6, 22.6, 14.1 (Fig.S8). Elemental analysis for C84H105N3O3, calcd: (%)C, 83.74; H, 8.78; N, 3.49. Found: (%) C, 83.63; H, 8.65; N, 3.57. MALDI-TOF MS, m/z (%): calcd for 1205.8 [M+H]+, found: 1206.0 (100) [M+H]+ (Fig.S9).

Reference： [1]Tetrahedron,2014,vol. 70,p. 3935 - 3942

36
[ 1268633-80-2 ]
[ 365564-05-2 ]
[ 1609557-99-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 24h;Inert atmosphere; Reflux;	General procedure: A mixture of <strong>[365564-05-2]1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene</strong> (0.20 g, 0.44 mmol), compound 2 (0.78 g, 1.71 mmol), and K2CO3 (0.60 g, 4.4 mmol) in distilled water (20 mL) and toluene (20 mL) was charged and bubbled by nitrogen for 15 min, then Pd(PPh3)4 (20 mg) was added. The mixture was refluxed for 24 h under nitrogen. After cooling to room temperature, the mixture was extracted with dichloromethane for three times. Then the organic phase was combined and dried over anhydrous Na2SO4. Removing the solvent under reduced press, the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, v/v=3/1) to give a light yellow oil (0.14g). Yield: 27%. 1H NMR (500 MHz, CDCl3, ppm): delta 8.85 (d, J=1.5 Hz, 3H), 8.58 (d, J=1.5 Hz, 3H), 8.18-8.16 (m, 3H), 8.06 (s, 3H), 8.01-7.99 (m, 3H), 7.59 (d, J=8.5 Hz, 3H), 7.46 (d, J=8.5 Hz, 3H), 4.39 (t, J=7,7 Hz, 6H), 2.74 (s, 9H), 1.97-1.92 (m, 6H), 1.44-1.24 (m, 54H), 0.86 (t, J=6.5, 7.5 Hz, 9H) (Fig.S7). 13C NMR (100 MHz, CDCl3, ppm): delta 197.6, 143.6, 142.9, 140.8, 133.6, 128.9, 126.5, 126.2, 124.9, 123.8, 122.7, 122.1, 119.3, 109.6, 108.5, 53.4, 43.5, 31.9, 29.5, 29.4, 29.3, 29.0, 27.3, 26.6, 22.6, 14.1 (Fig.S8). Elemental analysis for C84H105N3O3, calcd: (%)C, 83.74; H, 8.78; N, 3.49. Found: (%) C, 83.63; H, 8.65; N, 3.57. MALDI-TOF MS, m/z (%): calcd for 1205.8 [M+H]+, found: 1206.0 (100) [M+H]+ (Fig.S9).

Reference： [1]Tetrahedron,2014,vol. 70,p. 3935 - 3942

37
[ 773134-11-5 ]
[ 365564-05-2 ]
C₃₀H₁₈F₆O₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650

38
[ 179232-29-2 ]
[ 365564-05-2 ]
C₃₀H₂₁F₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,4-dioxane; water; at 90℃; for 24h;Inert atmosphere;	Synthesis of Compound 6: A mixture of compound 1 (0.91g, 2.0 mmol) and methyl 2-fluoro-4-bromon-benzoate (1.6 g, 6.5 mmol) was dissolved in 48 mL mixed solvent of p-dioxane/H20 (1:1 v/v), which was de-oxygenated by three freeze-pump-thaw cycles and protected under N2 atmosphere. After quickly adding of CsF (2.7 g, 18 mmol) and Pd(dppf) Cl2 (0.11 g, 0.15 mmol), the suspension was heated and stirred vigorously at 90 C for 24 hours. After cooling down to room temperature, the resulting suspension was added with 200 mL of 20% NH4CI solution, and extracted three times with 70 mL EtOAc using a 250-mL separatory funnel. The organic layers were combined, washed with saturated brine, dried with anhydrous Na2S04 and filtered. A crude product was obtained after removing all the solvent by rotary evaporation, and further purified by quick chromatography using ClH C^/Hexane (8:1 v/v) as eluent (55% isolated yield) . 1E NMR (400 MHz, DMSO-d6, delta) : 8.17 (s, 3H, Ar H) , 8.05 (d, J = 12.0 Hz, 3H, Ar H) , 7.95 (m, 6H, Ar H) , 3.90 (s, 9H, -COOCH3) .

Reference： [1]Patent: WO2015/157239,2015,A1 .Location in patent: Paragraph 00121; 00129
[2]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650

39
[ 99548-55-7 ]
[ 365564-05-2 ]
C₃₃H₃₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,4-dioxane; water; at 90℃; for 24h;Inert atmosphere;	Synthesis of Compound 7: A mixture of compound 1 (0.91g, 2.0 mmol) and methyl 2-methyl-4-bromon-benzoate (1.6 g, 6.5 mmol) was dissolved in 48 mL mixed solvent of p-dioxane/H20 (1:1 v/v), which was de-oxygenated by three freeze-pump-thaw cycles and protected under N2 atmosphere. After quickly adding of CsF (2.7 g, 18 mmol) and Pd(dppf)Cl2 (0.11 g, 0.15 mmol), the suspension was heated and stirred vigorously at 90 C for 24 hours. After cooling down to room temperature, the resulting suspension was added with 200 mL of 20% NH4CI solution, and extracted three times with 70 mL EtOAc using a 250-mL separatory funnel. The organic layers were combined, washed with saturated brine, dried with anhydrous Na2S04 and filtered. A crude product was obtained after removing all the solvent by rotary evaporation, and further purified by quick chromatography using ClH C^/Hexane (8:1 v/v) as eluent (55% isolated yield) . 1H NMR (400 MHz, CDC13, delta) : 8.05 (d, J = 8.0 Hz, 3H, Ar H) , 7.82 (s, 3H, Ar H) , 7.56 (m, 6H, Ar H) , 3.93 (s, 9H, -COOCH3) , 2.71 (s, 9H, -CH3) .

Reference： [1]Patent: WO2015/157239,2015,A1 .Location in patent: Paragraph 00121; 00131
[2]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650

40
[ 89976-27-2 ]
[ 365564-05-2 ]
C₃₀H₂₁N₃O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium phosphate; tetrabutylammomium bromide; palladium diacetate; In tetrahydrofuran; at 70℃; for 48h;Inert atmosphere;	Synthesis of Compound 8: A mixture of methyl-4-iodo-3- nitrobenzoate (10 g, 33 mmol) , Pd(AcO)2 (75 mg, 0.22 mmol) , (Bu) 4NBr (125 mg) , and K3P04 (13.5 g) in THF (300 mL) was added to 1 (5.0 g, 11 mmol) . The mixture was refluxed at 70 C for 48 h under argon atmosphere. The solution was filtered through Celite and the filtered solution was evaporated. Purification of the crude product by flash column chromatography on silica gel (fourth spot, hexane:EtOAc = 3:2, i?f = 0.35) provided pale yellow powders (3.0 g, 46% yield). XH NMR (DMSO-d<5, 400 MHz, delta) : 8.51 (s, 3H) , 8.30 (d, 3H, J = 8.0 Hz), 7.78 (d, 3H, J = 8.0Hz), 7.58 (s, 3H) , 3.94 (s, 9H) . 13C NMR (DMSO-d<5, 400 MHz, delta) : 164.8, 148.8, 138.7, 137.8, 133.7, 133.6, 130.9, 128.0, 125.5, 53.4. FT-IR (KBr, crrr1) 3488 (br) , 3086 (w) , 2955 (w) , 2850 (w) , 1729 (vs) , 1619 (m) , 1534 (vs) , 1437 (m) , 1355 (m) , 1289 (s), 1260 (m) , 1194 (w) , 1152 (w) , 1119 (m) , 980 (w) , 905(w) , 855 (w) , 824 (w) , 813 (w) , 759 (m) , 708 (w) , 416 (w).

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2641 - 2650
[2]Patent: WO2015/157239,2015,A1 .Location in patent: Paragraph 00133; 00134

41
[ 365564-05-2 ]
C₃₀H₂₇N₃O₆ [ No CAS ]