[ CAS No. 102587-98-4 ] {[proInfo.proName]}

Name: 102587-98-4|2,7-Dibromopyrene|95%
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Quality Control of [ 102587-98-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 102587-98-4 ]

CAS No. :	102587-98-4	MDL No. :	MFCD09909862
Formula :	C₁₆H₈Br₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IGTQPXMEWQTTBJ-UHFFFAOYSA-N
M.W :	360.04	Pubchem ID :	13615479
Synonyms :

Calculated chemistry of [ 102587-98-4 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	85.55
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.29
Log Po/w (XLOGP3) :	6.41
Log Po/w (WLOGP) :	6.11
Log Po/w (MLOGP) :	5.9
Log Po/w (SILICOS-IT) :	6.08
Consensus Log Po/w :	5.56

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.77
Solubility :	0.0000614 mg/ml ; 0.00000017 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.2
Solubility :	0.000226 mg/ml ; 0.000000627 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.24
Solubility :	0.00000207 mg/ml ; 0.0000000057 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.53

Safety of [ 102587-98-4 ]

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

Application In Synthesis of [ 102587-98-4 ]

* 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 [ 102587-98-4 ]
Downstream synthetic route of [ 102587-98-4 ]

[ 102587-98-4 ] Synthesis Path-Upstream 1~3

1
[ 17533-36-7 ]
[ 102587-98-4 ]

Reference： [1] Journal of the American Chemical Society, 2002, vol. 124, # 17, p. 4701 - 4707
[2] Journal of Organic Chemistry, 1986, vol. 51, # 14, p. 2847 - 2848
[3] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 49 - 57

2
[ 781-17-9 ]
[ 102587-98-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6430 - 6434[2] Angew. Chem., 2014, vol. 126, # 25, p. 6548 - 6552,5
[3] Journal of the American Chemical Society, 2002, vol. 124, # 17, p. 4701 - 4707
[4] Journal of Organic Chemistry, 1986, vol. 51, # 14, p. 2847 - 2848
[5] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 49 - 57

3
[ 129-00-0 ]
[ 102587-98-4 ]

Reference： [1] Chemistry - A European Journal, 2012, vol. 18, # 16, p. 5022 - 5035
[2] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 49 - 57
[3] Patent: WO2013/185871, 2013, A1,
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6430 - 6434[5] Angew. Chem., 2014, vol. 126, # 25, p. 6548 - 6552,5
[6] Chemical Communications, 2016, vol. 52, # 75, p. 11227 - 11230

[ 102587-98-4 ] Synthesis Path-Downstream 1~88

1
[ 17533-36-7 ]
[ 102587-98-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; for 12h;	2.50 g (11 mmol) of 2,3-dichloro-5,6-dicyano-p-quinone was added to a reaction in which 3.64 g (10 mmol) of Intermediate I-12(2) was dissolved in 50 ml of MC.After stirring the reaction solution for 12 hours,Filtration under celite filtered the palladium precipitate and the solvent was removed under vacuum to give 2.74 g (yield 76%) of intermediate I-12(3) compound.

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 4701 - 4707
[2]Journal of Organic Chemistry,1986,vol. 51,p. 2847 - 2848
[3]Patent: KR102090707,2020,B1 .Location in patent: Paragraph 0337-0340; 0347-0349
[4]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57

2
[ 129-00-0 ]
benzenediazonium-zinc-chloride [ No CAS ]
[ 102587-98-4 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 4701 - 4707

3
[ 781-17-9 ]
[ 102587-98-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6430 - 6434
Angew. Chem.,2014,vol. 126,p. 6548 - 6552,5
[2]Journal of the American Chemical Society,2002,vol. 124,p. 4701 - 4707
[3]Journal of Organic Chemistry,1986,vol. 51,p. 2847 - 2848
[4]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57
[5]Patent: KR102090707,2020,B1

4
[ 102587-98-4 ]
2,7-diethynylpyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 9393 - 9398
[2]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035

5
[ 1228384-93-7 ]
[ 102587-98-4 ]
[ 1228385-01-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 2606 - 2609

6
RuCl₃XH₂O [ No CAS ]
[ 102587-98-4 ]
[ 1204649-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water; acetonitrile;	a) The synthesis of the <strong>[102587-98-4]2,7-dibromopyrene</strong> is described in J. Org. Chem. 1986, 51, 2848. 5.3 g (25 mmol) NalO4, 25 mL H2O, and 0.14 g RuCl3xH2O are added to a solution of 1 g (2.8 mmol) <strong>[102587-98-4]2,7-dibromopyrene</strong> in 20 mL CH2Cl2 and 20 mL CH3CN. The dark brown suspension is heated to 50 C. overnight. The reaction mixture is poured into 100 mL of H2O, and extracted with 100 mL of THF. The organic phase is separated and concentrated. The crude product <strong>[102587-98-4]2,7-dibromopyrene</strong>-4,5,9,10-tetraone is obtained as red orange substance (yield <15%, m/z 420.0).

Reference： [1]Patent: US2011/152491,2011,A1

7
4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane [ No CAS ]
[ 102587-98-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(ll) bromide; In water; isopropyl alcohol; for 16h;Inert atmosphere; Reflux;	45.4 g (0.1 mol) of 2)2,-(2,7-pyrenediyl)bis(4>4,5,5-tetramethyl-1 ,3,2- dioxaborolane) and 111.5 g (0.5 mol) of copper(ll) bromide are suspended in 750 ml of i-PrOH and 300 ml of water. The reaction mixture is heated under reflux for 16 h. After cooling, the solid is separated off and washed three times with 200 ml of water. The residue is recrystallised from toluene. The content of product according to 1H-NMR is about 96% with an overall yield of 29.52 g (82%).

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873
[2]Patent: WO2013/185871,2013,A1 .Location in patent: Page/Page column 25
[3]Chemical Communications,2016,vol. 52,p. 11227 - 11230
[4]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035

8
[ 129-00-0 ]
[ 102587-98-4 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035
[2]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57
[3]Patent: WO2013/185871,2013,A1
[4]Angewandte Chemie - International Edition,2014,vol. 53,p. 6430 - 6434
Angew. Chem.,2014,vol. 126,p. 6548 - 6552,5
[5]Chemical Communications,2016,vol. 52,p. 11227 - 11230
[6]Patent: KR102090707,2020,B1

9
[ 124-38-9 ]
[ 102587-98-4 ]
[ 214622-81-8 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035
[2]Chemical Communications,2016,vol. 52,p. 11227 - 11230
[3]Journal of the American Chemical Society,2019,vol. 141,p. 10283 - 10293

10
[ 1208-86-2 ]
[ 102587-98-4 ]
[ 722499-18-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035

11
[ 102587-98-4 ]
[ 1066-54-2 ]
[ 1327238-68-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5022 - 5035
[2]Organometallics,2015,vol. 34,p. 3967 - 3978
[3]Science China Chemistry,2017,vol. 60,p. 561 - 569

12
[ 1453206-21-7 ]
[ 102587-98-4 ]
[ 1453206-29-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux;	In a nitrogen atmosphere, 5.8 g (14.4 mmol) of Intermediate E, 2.6 g (7.2 mmol) of Intermediate PY3, 80 mg (0.36 mmol) of Pd(OAc)2, 216 mg (1.08 mmol) of P(t-Bu)3, and 2.0 g (21.8 mmol) of sodium t-butoxide were added to 200 ml of toluene and refluxed for 12 hours. After the reaction was completed, the solvent was removed by evaporation, 1,500 ml of methylene chloride and 1,500 ml of water were added to wash the resultant, and an organic layer was collected and dried using magnesium sulfate anhydride. Then, the resultant was purified by recrystallization and silica gel chromatography, and 2.5 g of Compound 43 was obtained (43% yield). [0179] H-NMR (CDCl3, 300 MHz, ppm): 8.0-7.3 (m, 8H), 7.1-6.9 (m, 16H), 6.8-6.6 (m, 6H). [0180] MS (MALDI-TOF) m/z: 996 [M]+.

Reference： [1]Patent: US2013/228752,2013,A1 .Location in patent: Paragraph 0177; 0178; 0179; 0180

13
[ 123324-71-0 ]
[ 102587-98-4 ]
2,7-bis-(4-tert-butylphenyl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: 2,7-Dibromopyrene 6 (1.64g, 4.56mmol) and boronic acid (7a, b, or c; 10.9mmol, 2.4 equivalents) were suspended in toluene (137mL), ethanol (13.7mL) and K2CO3 (2N solution in water, 23mL). The mixture was purged with argon for 45min. Catalytic amounts of 18-crown-6 and Pd(PPh3)4 were added and the mixture was refluxed for 24h in the dark. The reaction was stopped and left to cool. The obtained solid was washed with cold acetone and was recrystallized from toluene to yield the pure product.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57
[2]Tetrahedron,2015,vol. 71,p. 308 - 314

14
[ 5720-07-0 ]
[ 102587-98-4 ]
2,7-bis(4-methoxyphenyl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		General procedure: 2,7-Dibromopyrene 6 (1.64g, 4.56mmol) and boronic acid (7a, b, or c; 10.9mmol, 2.4 equivalents) were suspended in toluene (137mL), ethanol (13.7mL) and K2CO3 (2N solution in water, 23mL). The mixture was purged with argon for 45min. Catalytic amounts of 18-crown-6 and Pd(PPh3)4 were added and the mixture was refluxed for 24h in the dark. The reaction was stopped and left to cool. The obtained solid was washed with cold acetone and was recrystallized from toluene to yield the pure product.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57
[2]Angewandte Chemie - International Edition,2020,vol. 59,p. 7214 - 7218
Angew. Chem.,2020,vol. 132,p. 7281 - 7285,5

15
[ 1765-93-1 ]
[ 102587-98-4 ]
2,7-bis(4-fluorophenyl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		General procedure: 2,7-Dibromopyrene 6 (1.64g, 4.56mmol) and boronic acid (7a, b, or c; 10.9mmol, 2.4 equivalents) were suspended in toluene (137mL), ethanol (13.7mL) and K2CO3 (2N solution in water, 23mL). The mixture was purged with argon for 45min. Catalytic amounts of 18-crown-6 and Pd(PPh3)4 were added and the mixture was refluxed for 24h in the dark. The reaction was stopped and left to cool. The obtained solid was washed with cold acetone and was recrystallized from toluene to yield the pure product.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 272,p. 49 - 57

16
[ 12080-32-9 ]
2,7-(bistrimethylstannyl)-4,5,9,10-4,5,9,10-tetrahydropyrene [ No CAS ]
[ 102587-98-4 ]
C₉₆H₉₆Pt₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6430 - 6434
Angew. Chem.,2014,vol. 126,p. 6548 - 6552,5

17
[ 1066-45-1 ]
[ 102587-98-4 ]
2,7-(bistrimethylstannyl)-4,5,9,10-4,5,9,10-tetrahydropyrene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6430 - 6434
Angew. Chem.,2014,vol. 126,p. 6548 - 6552,5

18
[ 102587-98-4 ]
C₃₃H₂₁NOS [ No CAS ]

Reference： [1]New Journal of Chemistry,2014,vol. 38,p. 4404 - 4408

19
[ 102587-98-4 ]
C₃₆H₂₂N₂O₂S [ No CAS ]

Reference： [1]New Journal of Chemistry,2014,vol. 38,p. 4404 - 4408

20
[ 122-39-4 ]
[ 102587-98-4 ]
C₂₈H₁₈BrN [ No CAS ]

Reference： [1]New Journal of Chemistry,2014,vol. 38,p. 4404 - 4408

21
[ 102587-98-4 ]
[ 1204649-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; ruthenium(III) trichloride hydrate; In dichloromethane; water; acetonitrile; at 50℃;	The synthesis of the <strong>[102587-98-4]2,7-dibromopyrene</strong> is described in J. Org. Chem. 1986, 51, 2848. 5.3 g (25 mmol) NalO4, 25 mL H2O, and 0.14 g RuCl3xH2O are added to a solution of 1 g (2.8 mmol) <strong>[102587-98-4]2,7-dibromopyrene</strong> in 20 mL CH2Cl2 and 20 mL CH3CN. The dark brown suspension is heated to 50 C. overnight. The reaction mixture is poured into 100 mL of H2O, and extracted with 100 mL of THF. The organic phase is separated and concentrated. The crude product <strong>[102587-98-4]2,7-dibromopyrene</strong>-4,5,9,10-tetraone is obtained as red orange substance (yield<15%, m/z 420.0).

Reference： [1]Patent: US2014/357898,2014,A1 .Location in patent: Paragraph 0197

22
[ 102587-98-4 ]
[ 190843-93-7 ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 308 - 314

23
[ 102587-98-4 ]
quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine-[t-Bu]₂-[Cl]₄ [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 308 - 314

24
[ 102587-98-4 ]
2,7-bis(4-tert-butylphenyl)-4,5,9,10-tetraketopyrene [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 308 - 314

25
[ 102587-98-4 ]
quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine-[4-t-Bu-phenyl]2-[Cl]4 [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 308 - 314

26
[ 102587-98-4 ]
quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine-[t-Bu]₂-[SC12H25]₄ [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 308 - 314

27
[ 102587-98-4 ]
2,7-dibromopyrene-4,5,9,10-tetraalkoxypyrene [ No CAS ]

Reference： [1]Patent: US2014/357898,2014,A1

28
[ 102587-98-4 ]
5-(7-(5-(bis(4-methoxyphenyl)(phenyl)methoxy)pent-1-yn-1-yl)pyren-2-yl)pent-4-yn-1-ol [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 16191 - 16193

29
[ 102587-98-4 ]
C₅₆H₅₇N₂O₅P [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 16191 - 16193

30
[ 5390-04-5 ]
[ 102587-98-4 ]
5,5'-(pyrene-2,7-diyl)bis(pent-4-yn-1-ol) [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 16191 - 16193

31
[ 75-77-4 ]
[ 102587-98-4 ]
2,7-bis(trimethylsilyl)pyrene [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10511 - 10516

32
chlorotris(9-decenyl)silane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(tri-9-decenylsilyl)pyrene [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10511 - 10516

33
[ 101-70-2 ]
[ 102587-98-4 ]
2,7-bis(dianisylamino)pyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 137 - 145

34
[ 25069-74-3 ]
[ 102587-98-4 ]
C₅₆H₄₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With palladium diacetate; sodium carbonate; In N,N-dimethyl-formamide; at 110℃; for 2h;Glovebox;	Flask compound A 1.2g (0.0035mol, 1eq), compound B 2.26g (0.00833 mol, 1.24eq) was added and the Na2CO3 0.72g (2eq). Then put the palladium (II) acetate 0.092g (0.04eq) in the glove box, and then to put the semi 60ml DMF was reacted for 2 hours at 120 . Then it extracted using chloroform with demineralized water and dried with MgSO4. With acetone and then filtered liquid was purified by column chromatography (MC: hexane = 1: 2) to yield 0.54g of the compound represented by Formula 7a. The yield was 21%.
21%	With palladium diacetate; sodium carbonate; In N,N-dimethyl-formamide;Glovebox; Heating;	Compound A 1.2 g (0.0033mol, 1eq), compound B 2.26 g (0.00833 mol, 1.24eq) and Na2CO3 0.72 g (2eq) were added to a flask. Palladium (II) acetate 0.092 g(0.04eq) was added to glove box, DMF 60ml was added and reacted at 120 degreesC for 4 hours. The resulting mixture was extracted using chloroform and demineralized water and dried with MgSO4. The filtered liquid was washed with acetone and purified by column chromatography (MC: hexane = 1: 2) to yield 0.54g of the compound represented by Formula 7a. The yield was 21%.

Reference： [1]Patent: KR2015/136461,2015,A .Location in patent: Paragraph 0253-0258
[2]Patent: KR2015/108209,2015,A .Location in patent: Paragraph 0253-0256

35
[ 102587-98-4 ]
C₃₅H₂₄BrNO [ No CAS ]

Reference： [1]Patent: KR2015/54654,2015,A

36
[ 102587-98-4 ]
C₃₅H₂₂BrN [ No CAS ]

Reference： [1]Patent: KR2015/54654,2015,A

37
[ 102587-98-4 ]
C₄₁H₂₆BrN [ No CAS ]

Reference： [1]Patent: KR2015/54654,2015,A

38
[ 102587-98-4 ]
C₅₃H₃₆N₂ [ No CAS ]

Reference： [1]Patent: KR2015/54654,2015,A

39
[ 102587-98-4 ]
[ 2835-77-0 ]
C₂₉H₁₈BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With copper(l) iodide; potassium carbonate; In diphenylether; at 180℃; for 30h;Inert atmosphere;	In 500mL reaction flask, <strong>[102587-98-4]2,7-dibromopyrene</strong> in a nitrogen atmosphere alkylene 30.0g (83.3mmol), compound [11]10.0g (83.3mmol), copper iodide (CuI) 15.9g(83.3mmol), potassium carbonate 25.3 Insert the diphenyl ether in 100mL g (183.3mmol) was stirred for 30 hours at 180 heating. Lower the temperature toroom temperature After the reaction, the mixture was stirred after adding 300mL of methanol and then filtered under reduced pressure, and the residue wasfiltered under reduced pressure, stirring was again added to 250mL acetone and 500mL distilled water. Remove the solid by silica gel chromatographypurification to give the light yellow solid intermediate compound of [158-1]5.6g (14%).

Reference： [1]Patent: KR2015/54654,2015,A .Location in patent: Paragraph 0187-0190

40
C₄₄H₅₇BO₄ [ No CAS ]
[ 102587-98-4 ]
C₉₂H₉₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80℃; for 48h;Inert atmosphere;	General procedure: Compound 1100: <strong>[102587-98-4]2,7-dibromopyrene</strong> (360 mg, 1 mmol), 2,6-diynylphenyl borate (2.5 mmol) and K2C03 (552 mg, 4 mmol) were dissolved in toluene (80 mL) and water (20 mL) solution. Pd(PPh3)4(116 mg, 0.1 mmol) was added to the solution before degassing the mixture via bubbling nitrogen for 30 mm. The resulting mixture was stirred under a N2 atmosphere at 80 C for 48 h. After the reaction was complete, the mixture was diluted with DCM, washed with H20 and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography to give compound 1100. llOOa: ?H NIVIR (400 MHz, cdcl3) oe 8.63 (s, 4H), 8.20 (s, 4H), 7.76 (s, 4H), 7.03 (d, J= 8.9 Hz,8H), 6.61 (d, J= 8.9 Hz, 8H), 3.76 (t, J= 6.6 Hz, 8H), 1.67 (m, 8H), 1.50 (s, 18H), 1.39- 1.23 (m, 24H),0.87 (t, J= 6.9 Hz, 12H). ?3C NIVIR (100 MHz, cdcl3) oe 159.21, 150.39, 142.62, 136.69, 132.86, 130.74,129.42, 127.72, 127.64, 124.33, 123.65, 114.98, 114.51, 92.69, 88.63, 68.02, 34.79, 31.65, 31.37, 29.19,25.72, 22.68, 14.13.

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10427 - 10430
Angew. Chem.,2016,vol. 128,p. 10583 - 10586,4
[2]Patent: WO2016/149633,2016,A1 .Location in patent: Page/Page column 22; 53

41
C₅₂H₇₃BO₄ [ No CAS ]
[ 102587-98-4 ]
C₁₀₈H₁₃₀O₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10427 - 10430
Angew. Chem.,2016,vol. 128,p. 10583 - 10586,4

42
C₄₀H₅₃BO₂S₂ [ No CAS ]
[ 102587-98-4 ]
C₈₄H₉₀S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 24h;	?HNMR (400 IVIHz, cdcl3) oe 8.54 (s, 4H), 8.18 (s, 4H), 7.70 (s, 4H), 6.67 (d, J= 3.6 Hz, 4H), 6.43 (d, J= 3.6 Hz, 4H), 2.59 (t, J= 7.5 Hz, 8H), 1.46 (s, 18H), 1.24 (m, 32H), 0.87-0.80 (m, 12H). ?3C NIVIR (100 IVIHz, cdcl3) oe 150.39, 148.57, 142.42, 136.12, 131.95, 130.84, 129.37, 127.78, 127.33,124.36, 124.17, 124.15, 123.35, 120.39, 92.93, 86.47, 34.81, 31.62, 31.49, 31.34, 30.24, 28.79, 22.67,14.17.

Reference： [1]Canadian Journal of Chemistry,2017,vol. 95,p. 341 - 345
[2]Patent: WO2016/149633,2016,A1 .Location in patent: Page/Page column 22; 23; 56; 57

43
[ 102587-98-4 ]
[ 927-74-2 ]
2,7-bis(4-hydroxybut-1-yn-1-yl)pyrene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9961 - 9964
Angew. Chem.,2016,vol. 128,p. 10115 - 10118,4

44
[ 102587-98-4 ]
2-[4-(4,4’-dimethoxytriphenylmethyloxy)but-1-yn-1-yl]-7-(4-hydroxyhex-1-yn-1-yl)pyrene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9961 - 9964
Angew. Chem.,2016,vol. 128,p. 10115 - 10118,4

45
[ 102587-98-4 ]
C₅₄H₅₃N₂O₅P [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9961 - 9964
Angew. Chem.,2016,vol. 128,p. 10115 - 10118,4

46
[ 29875-73-8 ]
[ 102587-98-4 ]
C₅₂H₃₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux;	Under nitrogen atmosphere, intermediate-1 (1.7 g, 7.2 mmole),<strong>[102587-98-4]2,7-dibromopyrene</strong> (1.3 g, 3.6 mmole),Palladium (II) acetate (Pd (OAc) 2) (40 mg, 0.18 mol), P (t-Bu) 3 (108 mg, 0.54 mmol) and sodium t-butoxide (1.0 g, 10.9 mmol)Was added to toluene (100 ml) and refluxed for 24 hours.After the reaction was completed, the solvent was removed by evaporation,After 1000 ml of methylene chloride and 1000 ml of water were added and washed,The organic layer was collected and dried over anhydrous magnesium sulfate.Subsequent recrystallization and separation by silica gel chromatography gave compound 1 (0.98 g, 40% yield).

Reference： [1]Patent: KR2015/19724,2015,A .Location in patent: Paragraph 0247; 0248; 0249; 0250; 0251; 0252

47
4-pyridyl methylbromoborane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(methyl(pyridin-4-yl)boryl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With n-butyllithium; 5%-palladium/activated carbon; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Under nitrogen, <strong>[102587-98-4]2,7-dibromopyrene</strong> was added to a 500 mL three-necked flask0.01mol, 4-pyridyl methylbromoborane, 0.1 g of 5% palladium on carbon and 100 mL of anhydrous tetrahydrofuran were cooled to 0 C and 33 mL of 1 M butyl n-butyllithium solution was added dropwise. The reaction mixture was stirred and stirred to continue reaction 24 hours,Heated to 25 C, add water 100mL, concentrated under reduced pressure, adding ethyl acetate 300mL,The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The solid was purified by vacuum sublimation to give 2,7-bis(methyl(pyridin-4-yl)boryl)pyrene (A) 79%

Reference： [1]Patent: CN103450240,2016,B .Location in patent: Paragraph 0035; 0036

48
4-pyridyl butylbromoborane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(butyl(pyridin-4-yl)boryl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With n-butyllithium; 5%-palladium/activated carbon; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 0.01 mol of <strong>[102587-98-4]2,7-dibromopyrene</strong>, 0.021 mol of 4-pyridyl butylbromoborane, 0.1 g of 5% palladium on carbon and 100 mL of anhydrous tetrahydrofuran were added to a 500 mL three-necked flask and cooled to 0 C,A solution of 10 mL of n-butyllithium in hexane was added dropwise and the mixture was stirred and stirred for 24 hours.After heating to 25 C, 100 mL of water was added and the mixture was concentrated under reduced pressure. 300 mL of ethyl acetate was added. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The solid was purified by vacuum sublimation to give 2,7-bis(butyl(pyridin-4-yl)boryl)pyrene (B) in a yield of 62%

Reference： [1]Patent: CN103450240,2016,B .Location in patent: Paragraph 0037; 0038

49
4-pyridyl hexylbromoborane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(hexyl(pyridin-4-yl)boryl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With n-butyllithium; 5%-palladium/activated carbon; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 0.01 mol of <strong>[102587-98-4]2,7-dibromopyrene</strong> was added to a 500 mL three-necked flask,4-pyridyl hexylbromoborane, 0.021 mol,5% palladium on charcoal 0.1 g and anhydrous tetrahydrofuran 100 mL, cooled to 0 C,A solution of 10 mL of n-butyllithium in hexane was added dropwise and the mixture was stirred and stirred for 24 hours.The temperature was raised to 25 C, 100 mL of water was added, concentrated under reduced pressure, and ethyl acetate was added300 mL, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The solid was purified by vacuum sublimation, 2,7-bis(hexyl(pyridin-4-yl)boryl)pyrene(C) in a yield of 54%

Reference： [1]Patent: CN103450240,2016,B .Location in patent: Paragraph 0039; 0040

50
4-pyridyl dodcecylbromoborane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(dodecyl(pyridin-4-yl)boryl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With n-butyllithium; 5%-palladium/activated carbon; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 0.01 mol of <strong>[102587-98-4]2,7-dibromopyrene</strong> and 0.021 mol of 4-pyridyl dodcecylbromoborane were added to a 500 mL three-5% palladium on charcoal 0.1 g and anhydrous tetrahydrofuran 100 mL, cooled to 0 C,A solution of 10 mL of n-butyllithium in hexane was added dropwise, and the mixture was stirred and stirred for 24 hours. The temperature was raised to 25 C,After adding 100 mL of water, the mixture was concentrated under reduced pressure, and 300 mL of ethyl acetate was added. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The solid was purified by vacuum sublimation to give 2,7-bis(dodecyl(pyridin-4-yl)boryl)pyrene (D) in a yield of 48%

Reference： [1]Patent: CN103450240,2016,B .Location in patent: Paragraph 0041; 0042

51
4-pyridyl hexadecylbromoborane [ No CAS ]
[ 102587-98-4 ]
2,7-bis(hexadecyl(pyridin-4-yl)boryl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With n-butyllithium; 5%-palladium/activated carbon; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 0.01 mol of <strong>[102587-98-4]2,7-dibromopyrene</strong> and 0.021 mol of 4-pyridyl hexadecylbromoboranewere added to a 500 mL three-5% palladium on charcoal 0.1 g and anhydrous tetrahydrofuran 100 mL, cooled to 0 C,A solution of 10 mL of n-butyllithium in hexane was added dropwise and the mixture was stirred and stirred for 24 hours.The temperature was raised to 25 C, 100 mL of water was added, concentrated under reduced pressure, and 300 mL of ethyl acetate was added. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The solid was purified by vacuum sublimation, 2,7-bis(hexadecyl(pyridin-4-yl)boryl)pyrene (E) in a yield of 43%.

Reference： [1]Patent: CN103450240,2016,B .Location in patent: Paragraph 0043; 0044

52
[ 6783-05-7 ]
[ 102587-98-4 ]
C₃₂H₂₂ [ No CAS ]

Reference： [1]Chemistry of Materials,2017,vol. 29,p. 3580 - 3588

53
[ 101-70-2 ]
[ 102587-98-4 ]
2-bromo-7-(di-4-anisylamino)pyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 5111 - 5121

54
[ 1692-15-5 ]
[ 102587-98-4 ]
2,7-di(pyridin-4-yl)pyrene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 776 - 784

55
[ 102587-98-4 ]
[ 74-88-4 ]
[ 15679-24-0 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873

56
[ 102587-98-4 ]
1,6-dinitro-2,7-dimethylpyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873

57
[ 102587-98-4 ]
1,6-diamino-2,7-dimethylpyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873

58
[ 102587-98-4 ]
1-nitro-2,7-dimethylpyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873

59
[ 102587-98-4 ]
1-amino-2,7-dimethylpyrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873

60
[ 102587-98-4 ]
C₃₀H₁₉BrN₂O [ No CAS ]

Reference： [1]Patent: CN108218787,2018,A

61
[ 102587-98-4 ]
C₄₂H₂₉N₃O [ No CAS ]

Reference： [1]Patent: CN108218787,2018,A

62
[ 5419-55-6 ]
[ 102587-98-4 ]
C₁₆H₁₀BBrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃; for 2.5h;Inert atmosphere;	Add 100 mL of THF to a three-necked flask containing 2,7-dibromoindole (15.2 g, 42.4 mmol).Nitrogen protection, stirring at -78 C for 30 minutes, then adding 21 mL of n-butyl lithium (2.5 M), reaction for 1 hour,Add 14g of triisopropyl borate and react at low temperature for 1 hour.Gradually return to room temperature.After the treatment, 2M hydrochloric acid was added to the system to make the pH of the solution 4-5, and the solution was separated and the aqueous layer was extracted with ethyl acetate. The organic layer was combined and dried to give intermediate 3 (10.1 g, yield 80%) ).

Reference： [1]Patent: CN108218787,2018,A .Location in patent: Paragraph 0094-0097

63
[ 76-86-8 ]
[ 102587-98-4 ]
C₅₂H₃₈Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		Step1. Take 100mmol of 2,7-dibromofluorene,Add in anhydrous THF to dissolve,Cool down to -78 C,Add 2.5 equivalents of n-butyl lithium,Reacting at this temperature for 2 hours,Add 2 equivalents of triphenylchlorosilane,Gradually warm to room temperature,The reaction was for 1 hour.After the reaction is completed,Deionized water,The organic phase was extracted with EtOAc.The organic phase is dry,concentrate,Column chromatography,The product was obtained in 60 mmol.The yield was 60%.

Reference： [1]Patent: CN108264521,2018,A .Location in patent: Paragraph 0053; 0054; 0055

64
C₁₈H₁₄ClP [ No CAS ]
[ 102587-98-4 ]
C₅₂H₃₆P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		Step1. Take 100mmol of 2,7-dibromofluorene,Add in anhydrous THF to dissolve,Cool down to -78 C,Add 2.5 equivalents of n-butyl lithium,Reacting at this temperature for 2 hours,Add 2 equivalents of 54-0,Gradually warm to room temperature,The reaction was for 1 hour.After the reaction is completed,Deionized water,The organic phase was extracted with EtOAc.The organic phase is dry,concentrate,Column chromatography,The product 54-1 80 mmol was obtained.The yield was 80%.

Reference： [1]Patent: CN108264521,2018,A .Location in patent: Paragraph 0056; 0057; 0058

65
C₁₈H₁₄ClP [ No CAS ]
[ 102587-98-4 ]
C₅₂H₃₆O₂P₂ [ No CAS ]

Reference： [1]Patent: CN108264521,2018,A

66
2-([1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole [ No CAS ]
[ 102587-98-4 ]
C₅₄H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	Add in the reactor2,7-dibromofluorene(2.88 g, 8 mmol), intermediate 3-1 (3.88 g, 14.34 mmol),Pd2(dba)3 (0.34g, 0.4mmol),P(t-Bu)3 (0.28g, 1.34mmol),NaOt-Bu (4.48g, 40mmol),Toluene solution 200mL,Reaction at 100 C for 24 h,After the reaction, the organic phase was extracted with diethyl ether and water.The organic layer was dried over MgSO 4Concentrated organic matter, column chromatography,Recrystallization gave Compound 3 (3.81 g, 72%).

Reference： [1]Patent: CN108484507,2018,A .Location in patent: Paragraph 0064; 0065; 0067

67
[ 1352643-05-0 ]
[ 102587-98-4 ]
C₄₀H₃₄ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7530 - 7534

68
N-(2-fluorophenyl)-9-phenyl-9H-carbazol-3-amine [ No CAS ]
[ 102587-98-4 ]
C₆₄H₄₀F₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-necked flask with magnetic stirring, followed by argon replacement followed by sodium tert-butoxide 18.1 g (0.188 mol),<strong>[102587-98-4]2,7-dibromopyrene</strong> 28.26 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(dibenzylideneacetone)dipalladium were successively added.After the addition was completed, the temperature was raised to 110 C by heating.Starting to add dropwise to 72.3 g of N-(2-fluorophenyl)-9-diphenyl-9H-carbazol-3-amine(purity 99%, 0.203 mol)A solution consisting of 100 ml of xylene is temperature controlled at 110-120 C.The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF.55.29 g of a yellow product were obtained with a purity of 99% and a yield of 78%.

Reference： [1]Patent: CN109503460,2019,A .Location in patent: Paragraph 0093-0097; 0100-0102

69
C₂₅H₂₀N₂ [ No CAS ]
[ 102587-98-4 ]
C₆₆H₄₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-neck bottle with magnetic stirringAfter argon replacement, 8.1 g (0.188 mol) of sodium tert-butoxide was added in that order.2,7-Dibromo-pyrene 28.26 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added.After the addition was completed, the temperature was raised to 110 C by heating.Starting to dropwise add a solution consisting of 70.73 g of N-phenyl-9-tolyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene.Temperature control 110-120 C.Cool down to 50 C,Add 100m deionized water to hydrolyze,Stir for 10 minutes,Filter, filter cake repeatedly boiled several times with DMF, obtaining 59.72g of yellow product,99% purity,The yield was 85%.

Reference： [1]Patent: CN109608384,2019,A .Location in patent: Paragraph 0088; 0091; 0095; 0096

70
8-fluoro-N,9-diphenyl-9H-carbazol-3-amine [ No CAS ]
[ 102587-98-4 ]
C₆₄H₄₀F₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-necked flask with magnetic stirring. After argon replacement, add 18.1 g (0.188 mol) of sodium t-butoxide and 28.26 g of <strong>[102587-98-4]2,7-dibromopyrene</strong> (purity 99%,0.0785 mol) and xylene 100 ml. After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating. Start to add dropwise a solution consisting of 71.54g of 8-fluoro-N,9-diphenyl-9H-carbazol-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene, temperature control 110-120 C . The mixture was cooled to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF to obtain 53.82 g of a yellow product, purity 99%, yield 78%.

Reference： [1]Patent: CN109503459,2019,A .Location in patent: Paragraph 0091; 0092; 0093; 0094; 0097; 0098; 0099

71
C₃₅H₂₃BN₂O₂ [ No CAS ]
[ 102587-98-4 ]
C₈₆H₅₀N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	(2) 10.28 g (0.02 mol) of intermediate E, 2,7-dibromoindole (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed.The reaction was carried out by adding 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium under a nitrogen atmosphere. Warming up to reflux,The plate is monitored until the reaction is complete, the reaction is terminated, and the reaction solution is dried.Add 100 ml of dichloromethane, dissolve it completely and pass through a silica gel column, add 100 ml of water to the filtrate, wash with water, separate the organic phase, spin it dry and cook twice with ethanol, and filter to obtain 7 g of white solid compound G126, yield 62 %.

Reference： [1]Patent: CN104987309,2019,B .Location in patent: Paragraph 0375-0380

72
4-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)benzeneboronic acid [ No CAS ]
[ 102587-98-4 ]
C₇₀H₄₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	(2) 8.28 g (0.02 mol) of intermediate A, 2,7-Dibromopyrene 3.6 g (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed, and tetrakis(triphenylphosphine)palladium 0.23 g (0.0002 mol) was added to carry out a reaction under nitrogen atmosphere, and the temperature was raised. Until reflux, the plate was monitored until the reaction was completed. The reaction was terminated. The reaction solution was spun dry. 100 ml of dichloromethane was added to dissolve it completely and passed through a silica gel column. The filtrate was added with 100 ml of water, washed with water, and the organic phase was separated and dried. The ethanol was boiled twice and filtered to obtain 7.04 g of a white solid compound G17.The yield was 75%.

Reference： [1]Patent: CN104987309,2019,B .Location in patent: Paragraph 0169-0174

73
C₂₅H₂₀N₂ [ No CAS ]
[ 102587-98-4 ]
C₆₆H₄₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide was sequentially added,<strong>[102587-98-4]2,7-dibromopyrene</strong> 28.26 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon replacement, add 1.6ml in turn.Tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition,The temperature was raised to 110 C by heating.Starting to dropwise add a solution consisting of 70.73 g of 8-methyl-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene.Temperature control 110-120 C. Cool down to 50 C,Add 100m deionized water to hydrolyze,Stir for 10 minutes, filter,The filter cake is boiled several times with DMF.Yielding 59.72 g of a yellow product,99% purity,The yield was 85%.

Reference： [1]Patent: CN109608385,2019,A .Location in patent: Paragraph 0090; 0093; 0094; 0095

74
C₂₅H₂₀N₂ [ No CAS ]
[ 102587-98-4 ]
C₆₆H₄₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide was sequentially added,2,7-Dibromopyrene 28.26 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon replacement, add 1.6ml in turn.Tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium.After the addition was completed, the temperature was raised to 110 C by heating. Starting to add dropwise a solution consisting of 70.73 g of 4-methyl-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene, temperature control 110-120 C.Cool down to 50 C,Hydrolysis by adding 100m deionized water, stir for 10 minutes, filter,The filter cake is boiled several times with DMF, obtaining 59.72g of yellow product, purity 99%,The yield was 85%.

Reference： [1]Patent: CN109608386,2019,A .Location in patent: Paragraph 0091; 0094; 0097; 0098; 0099

75
3-bromo-4-fluoro-9-phenyl-9H-carbazole [ No CAS ]
[ 102587-98-4 ]
C₆₄H₄₀F₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tri-tert-butyl phosphine; sodium ethanolate; bis(dibenzylideneacetone)-palladium(0); In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-necked flask with magnetic stirring, followed by argon replacement followed by sodium tert-butoxide 18.1 g (0.188 mol), 2,7-Dibromo-indole 28.26 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon replacement, add 1.6ml in turn.Tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition was completed, the temperature was raised to 110 C by heating. Start dropping in by71.54g of 4-fluoro-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneLiquid, temperature control 110-120 C. Cool down to 50 C, add 100m deionized water hydrolysis, stir for 10 minutes, filter, filter cake with DMF antiThe mixture was boiled several times to obtain 55.29 g of a yellow product, purity 99%, yield 78%.

Reference： [1]Patent: CN109721526,2019,A .Location in patent: Paragraph 0092; 0095; 0098-0099

76
[ 102587-98-4 ]
[ 551951-04-3 ]
2,7-bis(3,3'',6,6''-tetra(tert-butyl)-9'H-9,3':6',9''-tercarbazol-9-yl)pyrene [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2019,vol. 7,p. 5009 - 5018

77
bis[4-(N,N-dimethylamino)-2,6-xylyl]-2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborlan-2-yl)phenylborane [ No CAS ]
[ 102587-98-4 ]
C₇₂H₈₀B₂N₄ [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 5405 - 5422

78
C₂₅H₂₀N₂ [ No CAS ]
[ 102587-98-4 ]
C₆₆H₄₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere;	500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol),2,7-Dibromo-indole 28.26 g (purity 99%, 0.0785 mol) and dimethylbenzene 100 ml. After argon replacement again, add sequentially1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition was completed, the temperature was raised to 110 C by heating. Start dropping atIt consists of 70.73 g of 9-phenyl-N-tolyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene.The solution is temperature controlled at 110-120 C. Cool down to 50 C, add 100 m deionized water hydrolysis, stir for 10 minutes, filter, filter cakeThe DMF was repeatedly boiled several times to give 59.72 g of a yellow product with a purity of 99% and a yield of 85%.

Reference： [1]Patent: CN109608383,2019,A .Location in patent: Paragraph 0094; 0095; 0096; 0097; 0100; 0101; 0102

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[ 102587-98-4 ]
4-bromo-2,7-diiodopyrene [ No CAS ]