[ CAS No. 18648-66-3 ] {[proInfo.proName]}

Name: 18648-66-3|2-(4-Bromophenyl)-1,1-diphenylethylene|95%
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SKU: A420211
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2D 3D

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Quality Control of [ 18648-66-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18648-66-3 ]

SDS Specification

Alternatived Products of [ 18648-66-3 ]

Product Details of [ 18648-66-3 ]

CAS No. :	18648-66-3	MDL No. :	MFCD01790865
Formula :	C₂₀H₁₅Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HUCFDUOIMSRYAA-UHFFFAOYSA-N
M.W :	335.24	Pubchem ID :	630600
Synonyms :

Calculated chemistry of [ 18648-66-3 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	94.0
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.72
Log Po/w (XLOGP3) :	6.77
Log Po/w (WLOGP) :	5.93
Log Po/w (MLOGP) :	6.15
Log Po/w (SILICOS-IT) :	6.06
Consensus Log Po/w :	5.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-6.62
Solubility :	0.0000804 mg/ml ; 0.00000024 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.58
Solubility :	0.0000889 mg/ml ; 0.000000265 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.34
Solubility :	0.00000152 mg/ml ; 0.0000000045 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.39

Safety of [ 18648-66-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18648-66-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 18648-66-3 ]
Downstream synthetic route of [ 18648-66-3 ]

[ 18648-66-3 ] Synthesis Path-Upstream 1~8

1
[ 119-61-9 ]
[ 589-15-1 ]
[ 18648-66-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: at 150℃; for 24 h; Inert atmosphere Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran for 24 h;	40.00 g of p-bromobenzyl bromide (0.16 mol) and 83.6 mL of triethyl phosphite (0.48 mol) were added to a solution of 500 mlThree bottles,Magnetic stirring and argon, oil bath heated at 150 ° C for 24 hours, cooled to room temperature,Get Ye Lide reagent.To the three-necked flask was added 450 ml of tetrahydrofuran (THF), 21.87 g of benzophenone (0.12 mol) and 40.39 g of potassium tert-butoxide (t-BuOK, 0.36 mol) were added and the mixture was stirred for 24 h. After the reaction was stopped, The solution was poured into water and extracted with a large amount of white precipitate. The precipitate was collected by extraction with a funnel, washed three times with ethanol and dried in a vacuum at 60C for 24 h to give Tri-Br as a white intermediate.

Reference： [1] Patent: CN104341311, 2016, B, . Location in patent: Paragraph 0028; 0029; 0030
[2] Chinese Journal of Chemistry, 2015, vol. 33, # 8, p. 939 - 947

2
[ 119-61-9 ]
[ 38186-51-5 ]
[ 18648-66-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: at 0℃; Inert atmosphere Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2 h; Inert atmosphere	A solution of benzophenone (1.82g, 10 mmol) and diethyl 4-bromobenzylphosphonate (3.1 g, 10 mmol) in anhydrous THF (40 mL) was stirred under argon atmosphere at 0 ºC. Potassium tert-butoxide (1.1 g, 10 mmol) was added quickly and the mixture was stirred for 2 h at room temperature. The reaction mixture was poured into ethanol and a solid precipitated out. The precipitate was filtered and washed with ethanol (3×10 mL) to afford product 6 as a white powder (2.41g, 72percent). Mp 52−54 ºC; IR (KBr, cm^-1): 3032, 1610, 1484; ¹H NMR (300 MHz, CDCl₃): δ 7.25−7.18 (m, 3H), 7.16–7.06 (m, 5H), 7.05−6.94 (m, 4H), 6.92−6.82 (m, 3H); MS (EI): m/z 335, 337 (M⁺, M⁺+2, 95, 100percent).
72%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere	A solution of benzophenone (1.82 g, 10 mmol) and diethyl 4-bromobenzylphosphonate (3.1 g, 10 mmol) in anhydrous THF (40 mL) was stirred under argon atmosphere at 0°C. Potassium tert-butoxide (1.1 g, 10 mmol) was added quickly and the mixture was stirred for 2 h at room temperature. The reaction mixture was poured into ethanol (10 mL) and a solid precipitated out. The precipitate was filtered and washed with ethanol (310 mL) to afford 1 as a white powder (2.41 g, 72percent). Mp 52-54 °C; IR (KBr, cm^-1): 3032, 1610, 1484; ¹H NMR (300 MHz, CDCl₃): δ 7.25-7.18 (m, 3H), 7.16-7.06 (m, 5H), 7.05-6.94 (m, 4H), 6.92-6.82 (m, 3H); LCMS(EI): m/z 335 (MH⁺, 100percent).

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 24, p. 5695 - 5709
[2] Tetrahedron Letters, 2012, vol. 53, # 50, p. 6838 - 6842
[3] Dyes and Pigments, 2013, vol. 99, # 3, p. 740 - 747
[4] Patent: WO2009/51390, 2009, A2, . Location in patent: Page/Page column 64-65; 70-72
[5] Journal of Materials Chemistry, 2012, vol. 22, # 35, p. 18505 - 18513
[6] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1470 - 1478

3
[ 27329-60-8 ]
[ 1122-91-4 ]
[ 18648-66-3 ]

Reference： [1] Patent: JP2005/298421, 2005, A, . Location in patent: Page/Page column 27-28
[2] Chemistry Letters, 2016, vol. 45, # 5, p. 517 - 519
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5695 - 5698[4] Angew. Chem., 2018, vol. 130, # 20, p. 5797 - 5800,4

4
[ 530-48-3 ]
[ 673-40-5 ]
[ 18648-66-3 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1463 - 1469

5
[ 136350-66-8 ]
[ 98-80-6 ]
[ 18648-66-3 ]

Reference： [1] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1677 - 1686

6
[ 530-48-3 ]
[ 56075-37-7 ]
[ 18648-66-3 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 38, p. 5297 - 5303

7
[ 119-61-9 ]
[ 17211-08-4 ]
[ 18648-66-3 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1329 - 1333

8
[ 859777-18-7 ]
[ 18648-66-3 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 439

[ 18648-66-3 ] Synthesis Path-Downstream 1~87

1
[ 18648-66-3 ]
1-bromo-1-(4-bromo-phenyl)-2,2-diphenyl-ethene [ No CAS ]

Reference： [1]Journal of the Chemical Society,1949,p. 439

2
[ 859777-18-7 ]
[ 18648-66-3 ]

Reference： [1]Journal of the Chemical Society,1949,p. 439

3
2-(4-Bromo-phenyl)-4,4-diphenyl-[1,3]oxathiolan-5-one [ No CAS ]
[ 18648-66-3 ]

Reference： [1]Acta Chemica Scandinavica (1947),1968,vol. 22,p. 247 - 253

4
[ 930765-91-6 ]
[ 18648-66-3 ]
[ 930766-01-1 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 1913 - 1922

5
[ 18648-66-3 ]
[ 125643-81-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 5695 - 5709

6
[ 18648-66-3 ]
[ 288105-04-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 5695 - 5709
[2]Journal of Materials Chemistry,2008,vol. 18,p. 806 - 818
[3]Tetrahedron Letters,2012,vol. 53,p. 6838 - 6842
[4]Chinese Journal of Chemistry,2015,vol. 33,p. 939 - 947

7
[ 27329-60-8 ]
[ 1122-91-4 ]
[ 18648-66-3 ]

Reference： [1]Patent: JP2005/298421,2005,A .Location in patent: Page/Page column 27-28
[2]Chemistry Letters,2016,vol. 45,p. 517 - 519
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 5695 - 5698
Angew. Chem.,2018,vol. 130,p. 5797 - 5800,4

8
C₃₄H₃₆N₂ [ No CAS ]
[ 18648-66-3 ]
HTM-A [ No CAS ]

Reference： [1]Patent: JP2005/298421,2005,A .Location in patent: Page/Page column 28

9
[ 5419-55-6 ]
[ 18648-66-3 ]
[ 288105-04-4 ]

Yield	Reaction Conditions	Operation in experiment
		[Exemplary embodiment 8] Synthesis of compound 142 [Compound 142][Synthesis scheme] <n="72"/>(OH)2 K2CO3 P d(PPhOl4 THF Together with triethylphosphite (25g, ldeltaOmmol), 1- bromo-4-bromomethylbenzene (5g, 20mmol) was put into an agitator to have them react to each other for two hours at 120C to thereby synthesize triethyl A- bromobenzylphosphite. The synthesized triethyl 4- bromobenzylphosphite (6.1Aq, 2OmInOl), benzophenone (5.13g, 29.1betammol) and potassium tert-butoxide (3.27g, 29.1betammol) were put into a reactor and melted by THF of 50ml to have them react to each other for four hours at 120C to thereby synthesize l-bromo-4- (2, 2- diphenylvinyl) benzene (1-1) . The synthesized-bromo-4- (2, 2- diphenylvinyl) benzene (1-1) (beta.03g, ldeltammol) was melted by THF of 50ml, gradually added with 2Mn-BuLi (10ml, 20mmol) at -78 C and agitated for one hour at low temperatures. The mixture was gradually added with triisopropyl borate <n="73"/>(3.76g, 20mmol) at -78C, agitated for one hour at low temperatures and then additionally agitated for 30 minutes at 0C to thereby synthesize 4- (2, 2- diphenylvinyl) phenylboronic acid (1-2) . The synthesized 4- (2, 2-diphenylvinyl) phenylboronic acid (4.5g, 15mmol) (l-2), K2CO3 (6.2g, 45mmol) and Pd (PPh3) 4 (0.8betag, 0.75mmol) were melted by THF (60ml), added with (E) -3- (5- bromothieno [3, 2-b] thiophene-2-yl) -2-cyanoacrylic acid(5.6g, 18mmol) , agitated for four hours at 120C to complete the reaction. After extracting an organic layer from the mixture with dichloromethane and distilled water, the solvent was removed through an evaporator and the organic layer was recrystallized by n-hexane and dried to collect the compound 142 after the sediment was filtered.

Reference： [1]Patent: WO2009/51390,2009,A2 .Location in patent: Page/Page column 70-72

10
(Z)-3-(5-bromothiophen-2-yl)-2-cyanoacrylic acid [ No CAS ]
[ 18648-66-3 ]
C₂₈H₁₉NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[Exemplary embodiment 1] Synthesis of Compound 1 Compound 1[Reaction formula 1]n-BiotaiotaLiota THF Together with triethylphosphite (25g, 150mmol) , 1- bromo-4-bromomethylbenzene (5g, 20mmol) was put into an agitator to have them react to each other for two hours at 120C to thereby synthesize triethyl 4- bromobenzylphosphite . The synthesized triethyl 4- <n="66"/>bromobenzylphosphite (6.74g, 20mmol), benzophenone (5.13g, 29.16mmol) and potassium tert-butoxide (3.27g, 29.1betammol) were put into a reactor and melted by THF of 50ml to have them react to each other for four hours at 120C to thereby synthesize l-bromo-4- (2, 2-diphenylvinyl) benzene . After melted by THF 50ml, l-bromo-4- (2, 2- diphenylvinyl) benzene (6.03g, ldeltammol) was gradually added with 2Mn-BuLi (10ml, 20mmol) at -78C to be agitated for one hour at low temperatures. Again, the mixture was gradually added with (Z) -3- ( 5-bromothiophene-2-yl) -2- cyanoacrylic acid (5.1betag, 20mmol) at -78C, agitated for one hour at low temperatures and then additionally agitated for 30 minutes at 0C to complete the reaction.After extracting an organic layer from the mixture with dichloromethane and distilled water, the solvent was removed through a distiller, the organic layer was recrystallized by n-hexane, and dried and purified after filtering sediment (yield 52%) .1H NMR(CDCl3) : [ppm] = 8.04 (s, IH) , 7.67 (s, IH) , 7.60 (d, 3JHH = 3.6Hz, 2H) , 7.52 (d, 3JHH = 8.4Hz, 2H) , 7.43 (m, 3H) , 7.34 (m, 5H) , 7.19 (dd, 3JHH = 8Hz, 2H) , 7.14 (s, IH) , 7.07 (d, 3JHH = 8.4Hz, 2H) .

Reference： [1]Patent: WO2009/51390,2009,A2 .Location in patent: Page/Page column 64-65

11
[ 1007228-53-6 ]
[ 18648-66-3 ]
10-(4-(2,2-diphenylvinyl)phenyl)-10,10a-dihydroacridin-9(8aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate;palladium diacetate; In toluene; at 150℃; for 12h;	[Exemplary embodiment 9] Synthesis of compound 144 [Compound 144][Synthesis scheme] <n="74"/>KtBuO Pd(OAc)Toluene n -BuLi J ri isoprop yl bo rat e THF HCIlambdaH2 " l-bromo-4- (2, 2-diphenylvinyl) benzene (beta.03g, 18mmol) and 10, , 10, , -dihydroacridin-9 (8aH) -one (4.26g, 21.6mmol) were put into a reaction container, added with KtBuO(4.84g, 43.2mmol) and Pd (OAc) (0.24g, l.Odeltammol) and melted by toluene (50ml) to have them react to each other for 12 hours at 150C to thereby synthesize a compound 10- (4- (2, 2-diphenylvinyl) phenyl) -10, , 10, , -dihydroacridin- 9 (8aH) -one (3-1) . The synthesized compound 10-(4-(2,2- diphenylvinyl) phenyl) -10, , 10, , -dihydroacridin-9 (8aH) - <n="75"/>one (3-1) (3.2g, 7.08mmol) and triethyl A- bromobenzylphosphite (2.6g, 8.49mmol) were put into a reactor, added with KtBuO (0.95g, 8.49mmol), melted byTHF (50ml) and agitated for four hours at 120C to synthesize a compound (E) -9- (4-bromobenzylidene) -10- (4-(2, 2-diphenylvinyl) phenyl) -8a, 9, 10, ,10,,- tetrahydroacridine ( 3-2) . The synthesized compound (E) -9- ( 4-bromobenzylidene) -10- (4- (2,2-diphenylvinyl) phenyl) - 8a, 9, 10, , 10, , -tetrahydroacridine (3-2) (3.5g, 5.78mmol) was melted by THF of 30ml, gradually added with 2Mn-BuLi (3.45g, beta.9mmol) at -78C and agitated for one hour at low temperatures. The mixture was gradually added with triisoprophyl borate (1.29g, beta.9mmol) at -78C, agitated for one hour at low temperatures and then additionally agitated for 30 minutes at 0C to thereby synthesize a compound (E) -4- ( (10- (4- (2, 2-diphenylvinyl) phenyl) - 10, , 10, , -dihydroacridin-9 (8aH) - ylidene) methyl) phenylboronic acid (3-3) . The synthesized compound (E)-4-((10-(4- (2, 2-diphenylvinyl ) phenyl) - 10, , 10, , -dihydroacridin-9 (8aH) - ylidene) methyl) phenylboronic acid (3-3) (2.8g, 4.9mmol), K2CO3(2.03g, 14.7mmol) and Pd ( PPh3) 4 (0.8betag, 0.29mmol) were melted by THF (30ml), added with (E) -3- (5- bromothieno [3, 2-b] thiophene-2-yl) -2-cyanoacrylic acid (5.6g, ldeltammol) and agitated for four hours at 120C to <n="76"/>complete the reaction. After extracting an organic layer from the mixture with dichloromethane and distilled water, the solvent was removed through an evaporator and the organic layer was recrystallized by n-hexane, and dried to collect the compound 144 after the sediment was filtered.

Reference： [1]Patent: WO2009/51390,2009,A2 .Location in patent: Page/Page column 72-75

12
[ 80278-94-0 ]
[ 18648-66-3 ]
C₃₁H₂₇N [ No CAS ]

Reference： [1]Chemical Communications,2008,p. 5194 - 5196

13
[ 332083-44-0 ]
[ 18648-66-3 ]
[ 519171-68-7 ]

Yield	Reaction Conditions	Operation in experiment
60%		Into a 500 ml three-necked flask equipped with a condenser, 0.16 g (6.6 mmole) of magnesium, a small piece of iodine and 10 ml of tetrahydrofuran (THF) were placed under a stream of argon. After the resultant mixture was stirred at the room temperature for 30 minutes, a solution prepared by dissolving 1 g (3 mmole) of 1-(4-bromophenyl)-2,2-diphenylethylene into 10 ml of THF was added dropwise. After the addition was completed, the resultant mixture was stirred at 60C for 1 hours, and a Grignard reagent was prepared. Into a 500 ml flask equipped with a condenser, 0.6 g (1 mmole) of 9,10-dibromo-2,6-di(2-ethylhexyloxy)anthracene, 0.04 g (5% by mole) of dichlorobis(triphenylphosphine)palladium, 0.1 ml (1 M; 0.1 mmole) of a toluene solution of diisobutylaluminum hydride and 10 ml of THF were placed under a stream of argon. After the Grignard reagent prepared above was added dropwise to the obtained solution at the room temperature, the resultant mixture was heated under stirring for one night. After the reaction was completed, the reaction solution was cooled with ice water. The formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone successively, and 0.56 g of a yellow powder was obtained. The obtained yellow powder was identified to be Compound (A1) by the measurements in accordance with NMR, IR and the filed desorption mass spectroscopy (FD-MS) (the yield: 60%).

Reference： [1]Patent: EP1440959,2004,A1 .Location in patent: Page 20

14
[ 332083-46-2 ]
[ 332083-45-1 ]
[ 18648-66-3 ]
[ 519171-70-1 ]
[ 519171-69-8 ]

Yield	Reaction Conditions	Operation in experiment
		Into a 500 ml three-necked flask equipped with a condenser, 0.16 g (6.6 mmole) of magnesium, a small piece of iodine and 10 ml of THF were placed under a stream of argon. After the resultant mixture was stirred at the room temperature for 30 minutes, a solution prepared by dissolving 1 g (3 mmole) of 1-(4-bromophenyl)-2,2-diphenylethylene into 10 ml of THF was added dropwise. After the addition was completed, the resultant mixture was stirred at 60C for 1 hours, and a Grignard reagent was prepared. Into a 500 ml three-necked flask equipped with a condenser, 0.45 g (1 mmole) of 2,6/2,7-di-t-butyl-9,10-dibromoanthracene, 0.04 g (5% by mole) of dichlorobis(triphenylphosphine)palladium, 0.1 ml (1M; 0.1 mmole) of a toluene solution of diisobutylaluminum hydride and 10 ml of THF were placed under a stream of argon. After the Grignard reagent prepared above was added dropwise to the obtained solution at the room temperature, the resultant mixture was heated under stirring for one night. After the reaction was completed, the reaction solution was cooled with ice water. The formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone successively, and 0.4 g of a yellow powder was obtained. The obtained yellow powder was identified to be Compound (A2) by the measurements in accordance with NMR, IR and FD-MS (the yield: 50%).

Reference： [1]Patent: EP1440959,2004,A1 .Location in patent: Page 22

15
[ 1213241-16-7 ]
[ 18648-66-3 ]
[ 1213241-17-8 ]

Yield	Reaction Conditions	Operation in experiment
67%		Under the atmosphere of argon, 4-(2,2-diphenylvinyl)bromobenzene (10 g, 30 mmole, 3 eq) was dissolved into a mixed solvent composed of anhydrous toluene (45 ml) and anhydrous THF (45 ml), and the resultant solution was cooled to -20C in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.59 mmole/liter, 20 ml, 32 mmole, 1.06 eq) was added, and the obtained solution was stirred at -20C for 1 hour. To the resultant solution, 2-(2-phenyl-2-)propylanthraquinone (3.5 g, 11 mmole) was added, and the obtained mixture was stirred at the room temperature for 3 hours and then left standing for one night. To the resultant reaction mixture, a saturated aqueous solution of ammonium chloride (50 ml) was added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride and dried with magnesium sulfate. After the solvent was removed by distillation, the product was purified in accordance with the column chromatography (silica gel; hexane+50% dichloromethane, dichloromethane and finally dichloromethane+3% methanol), and a light yellow amorphous solid was obtained (5.7 g; the yield: 67%).

Reference： [1]Patent: EP1440959,2004,A1 .Location in patent: Page 22-23

16
[ 121-43-7 ]
[ 18648-66-3 ]
C₂₂H₂₁BO₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 1772 - 1779

17
[ 855004-46-5 ]
[ 18648-66-3 ]
[ 855004-55-6 ]

Yield	Reaction Conditions	Operation in experiment
59%		(1) Synthesis of 2-(2-biphenylyl)-9,10-bis(4-(2,2-diphenylvinyl)phenyl)-9,10-dihydroxy-9,10-dihydro anthracene; [Compound (B1-0)]; Under an atmospheric argon gas flow, 4-(2,2-diphenylvinyl)-1-bromobenzene in an amount of 9.8 g (29 mmol, 3 eq) was dissolved into a mixed solvent of anhydrous toluene in an amount of 45 milliliter and anhydrous THF in an amount of 45 milliliter, followed by cooling down to the temperature of - 20 C by means of dry ice / methanol bath. Adding hexane solution of n-butyllithium in an amount of 19 milliliter (1.59 mol/litter, 30 mmol; 1.04 eq), the resultant solution was stirred at the temperature of -20 C for 1 hour. Into the resultant solution, 2-(2-biphenylyl)-9,10-anthraquinone [Compound (A)] in an amount of 3.5 g (9.7 mmol) was added and after stirring at the room temperature for 2 hours, it was stood alone for a night. The resultant reaction mixture was deactivated with the use of saturated ammonium chloride aqueous solution in an amount of 50 milliliter, and the resultant solid was separated. The solid was washed use of the mixed solvent of hexane : dichloromethane = 1:1 (capacity ratio) and as a result, 5.0 g of white solid compound was obtained (yield: 59 %). The white solid was identified as the Compound (B1-0) in accordance with 1H-NMR. The measurement results of 1 H-NMR are shown as the following: 1H-NMR (CDCl3, TMS) delta 2.17 (1H, s), 2.66 (1H, s), 6.21 (2H, d, J=8Hz), 6.51 (2H, d, J=8Hz), 6.55 (4H, s), 6.80 (2H, d, J=4Hz), 7.0-7.4 (3H, m), 7.6-7.7 (3H, m)

Reference： [1]Patent: EP1695952,2006,A1 .Location in patent: Page/Page column 18-19

18
[ 119-61-9 ]
[ 17211-08-4 ]
[ 18648-66-3 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1329 - 1333

19
[ 121-43-7 ]
[ 18648-66-3 ]
[ 288105-04-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃;Inert atmosphere;	To a schlenk-type tube containing the solution of <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (5.36 g, 16.0 mmol) in 60 mL dried THF under N2 atmosphere at -78 C was added dropwise 1.6 M n-BuLi (12.7 mL, 20.4 mmol). The reaction mixture was stirred for 2 h at -78 C, and then trimethylborate (2.72 mL, 24.0 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by water, followed by acidifying with 25 mL HCl (6 M). The solution was extracted with ethylether. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified on a silica gel column using petroleum/ethyl acetate (v/v = 2:1) as eluent affording a white solid (2.40 g, yield 50.0%).1HNMR (CDCl3, 300 MHz, ppm) delta: 6.96-7.02 (m, 3H), 7.14 (br, 2H), 7.29-7.49 (m, 10H).13CNMR (CDCl3, 75.5 MHz, ppm) delta: 126.90, 127.20, 127.24, 127.42, 127.72, 127.88, 128.35, 128.38, 129.24, 130.04, 133.10, 139.15, 140.48, 143.22.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1329 - 1333

20
[ 18648-66-3 ]
[ 1203681-10-0 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

21
[ 18648-66-3 ]
[ 1203681-07-5 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

22
[ 18648-66-3 ]
[ 1203681-04-2 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

23
[ 18648-66-3 ]
[ 1203681-05-3 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

24
[ 18648-66-3 ]
[ 1203681-06-4 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

25
[ 18648-66-3 ]
[ 1203681-08-6 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

26
[ 18648-66-3 ]
[ 1203681-09-7 ]

Reference： [1]Patent: US2011/94588,2011,A1
[2]Patent: EP2341107,2011,A2

27
[ 18648-66-3 ]
[ 264282-36-2 ]
[ 1203681-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In toluene;Reflux; Inert atmosphere;	(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannan (0.81 g 2.66 mmol), <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (a compound of the Chemical Formula 2r) (1.7 g, 3.2 mmol), and Pd(PPh3)4 (0.15 g, 0.13 mmol) were dissolved in toluene (40 ml), and then refluxed under nitrogen atmosphere for 8 hours. Subsequently, an organic layer was extracted with methylene chloride and water and distilled, and column chromatography was performed (eluent-MC:Hx=1:4) to synthesize a compound of the Chemical Formula 4r.1H NMR (CDCl3): [ppm]=4.68 (s, 2H), 4.72 (s, 2H), 6.71 (s, 1H), 6.96 (s, 1H), 7.08 (s, 1H), 7.18 (m, 4H), 7.40 (m, 2H), 7.48 (m, 6H), 7.56 (d, 3JHH=8.8 Hz, 2H).
	tetrakis(triphenylphosphine) palladium(0); In toluene; for 8h;Inert atmosphere; Reflux;	[Example 6] Synthesis of a compound of the Chemical Formula 1r (6-1) (2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannan (0.81g 2.66mmol), <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (a compound of the Chemical Formula 2r) (1.7g, 3.2mmol), and Pd(PPh3)4 (0.15g, 0.13mmol) were dissolved in toluene (40ml), and then refluxed under nitrogen atmosphere for 8 hours. Subsequently, an organic layer was extracted with methylene chloride and water and distilled, and column chromatography was performed (eluent - MC : Hx = 1 : 4) to synthesize a compound of the Chemical Formula 4r.1H NMR(CDCl3) : [ppm] = 4.68(s, 2H), 4.72(s, 2H), 6.71(s, 1H), 6.96(s, 1H), 7.08(s, 1H), 7.18(m, 4H), 7.40(m, 2H), 7.48(m, 6H), 7.56(d, 3JHH = 8.8Hz, 2H).

Reference： [1]Patent: US2011/94588,2011,A1 .Location in patent: Page/Page column 31
[2]Patent: EP2341107,2011,A2 .Location in patent: Page/Page column 28; 37

28
[ 136350-66-8 ]
[ 98-80-6 ]
[ 18648-66-3 ]

Reference： [1]Chemistry - An Asian Journal,2010,vol. 5,p. 1677 - 1686

29
[ 18648-66-3 ]
[ 633-70-5 ]
C₅₄H₃₈Br₂O₂ [ No CAS ]

Reference： [1]Macromolecules,2010,vol. 43,p. 3613 - 3623

30
[ 80278-94-0 ]
[ 18648-66-3 ]
[ 1118752-92-3 ]

Yield	Reaction Conditions	Operation in experiment
9.98 g	With potassium tert-butylate; palladium diacetate; triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 125℃; for 10h;Inert atmosphere;	To a reaction vessel purged with nitrogen, 8.11 g of 2- (4-bromophenyl) -1,1-diphenylethylene, 4.24 g of 1,2,3,3a, 4,8b-hexahydrocyclopenta [b] indole, 56 mL of xylene was added, and 0.127 g of triphenylphosphine, 5.43 g of potassium t-butoxide, and 0.27 g of palladium acetate were added, followed by degassing under reduced pressure. The reaction was carried out for 10 hours while stirring at 125 C. Cool to 50 C, add 9.4 g of activated clay,After stirring for 1 hour, suction filtration was performed, 100 mL of water was added, and the mixture was stirred to extract an organic layer. The organic layer was washed with water, separated, dried over sodium sulfate, and concentrated under reduced pressure to obtain an oily crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: hexane / toluene = 10/1 (volume ratio)) to obtain a yellow solid (9.98 g). 2 g of the obtained yellow solid was brominated according to a conventional method to obtain 2.35 g of a bromo compound represented by the following formula (10).

Reference： [1]Organic Letters,2012,vol. 14,p. 1246 - 1249
[2]Dyes and Pigments,2011,vol. 91,p. 145 - 152
[3]Patent: JP2020/15898,2020,A .Location in patent: Paragraph 0171

31
[ 1315509-03-5 ]
[ 18648-66-3 ]
[ 1315509-04-6 ]

Reference： [1]Dyes and Pigments,2011,vol. 91,p. 145 - 152

32
[ 18648-66-3 ]
[ 1360085-06-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1246 - 1249

33
[ 18648-66-3 ]
[ 1092971-91-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1246 - 1249

34
[ 18648-66-3 ]
4-((3,3-dibutyl-1-(2-carboxyethyl)-3H-indolium-2-yl)methylene)-2-(4-(4-(2,2-diphenylvinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-3-oxocyclobut-1-enolate [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1246 - 1249

35
[ 2591-86-8 ]
[ 18648-66-3 ]
[ 17413-71-7 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18505 - 18513

36
[ 18648-66-3 ]
[ 1394943-32-8 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18505 - 18513

37
[ 18648-66-3 ]
[ 1394943-33-9 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18505 - 18513

38
[ 18648-66-3 ]
[ 87199-17-5 ]
[ 217449-95-1 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18505 - 18513

39
[ 18648-66-3 ]
[ 1262330-95-9 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6838 - 6842

40
[ 18648-66-3 ]
[ 1413339-39-5 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6838 - 6842

41
[ 18648-66-3 ]
C₂₂H₂₁BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution 6 (2.68 g, 8.0 mmol) in THF (30 mL) under argon atmosphere at -78 C was added n-BuLi (1.6 M, 6.3 mL, 10.2 mmol) dropwise. The reaction mixture was stirred for 2 h at -78 C. Trimethylborate (1.36 mL, 12.0 mmol) was added to the mixture at the same temperature. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by water (1 mL), followed by acidification with HCl (6M,12 mL). The mixture was stirred for a further 2 h. The product was extracted with ethyl acetate (3×50 mL). The organic layer was separated and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel/ethyl acetate: petroleum ether 1:1) afforded compound 8 as a white solid (1.45 g, 60%).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6838 - 6842

42
[ 18648-66-3 ]
[ 1123-56-4 ]
[ 1335328-82-9 ]

Reference： [1]Patent: US2012/330052,2012,A1

43
[ 18648-66-3 ]
[ 1123-56-4 ]
C₂₉H₂₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 6A tetrahydrofuran solution (25 mL) of 2-(4-bromophenyl)-1,1-diphenyl ethylene (2.0 g) was cooled to -78 C., and n-butyllithium (2.6 M, 2.6 mL) was gradually dropped therein. The resulting mixture was stirred at the same temperature for 2 hours. After addition of 2,6-dimethylbenzaldehyde (0.65 g), the mixture was stirred for 12 hours while slowly warming to 25 C. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of ammonium chloride, and the organic phase was extracted with ethyl acetate. The resulting organic phase was dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography.

Reference： [1]Patent: US2012/330052,2012,A1 .Location in patent: Page/Page column 8

44
[ 18648-66-3 ]
[ 1480740-66-6 ]

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

45
[ 18648-66-3 ]
[ 1480740-68-8 ]

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

46
[ 18648-66-3 ]
[ 1480740-70-2 ]

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

47
[ 18648-66-3 ]
[ 1480740-72-4 ]

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

48
[ 18648-66-3 ]
[ 5720-07-0 ]
[ 1480740-63-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate; In water; toluene; at 90℃; for 6h;Inert atmosphere;	General procedure: A mixture of <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (1) (2.0 g, 5.97 mmol) and phenylboronic acid (873 mg, 7.16 mmol) was dissolved in toluene (15 mL) under argon atmosphere. Aqueous solution of K2CO3 (2 mL, 2 M), tricaprylylmethylammoniumchloride (Aliquat336) (3 drops) and Pd(PPh3)4 (10 mg) was added to the mixture. The reaction mixture was heated at 90C for 6 h. After being cooled to room temperature, distilled water (5 mL) was added and extracted with dichloromethane (310 mL). Organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, the residue was purified using column chromatography (silica gel, ethyl acetate/petroleum ether 5:95) afforded 2 (240 mg, 85%) as a white solid. Mp 97-98C; IR (KBr,cm-1): 3015, 1601, 1493; 1H NMR (300 MHz, CDCl3): delta 7.53 (d, 2H, J=7.5 Hz), 7.42-7.20 (m, 15H), 7.08 (d, 2H, J=7.5 Hz), 6.99 (s, 1H); 13C NMR (75 MHz, CDCl3): delta 143.2, 142.5, 140.4, 140.3, 139.1, 136.3, 130.0, 129.9, 128.7, 128.6, 128.1, 127.6, 127.5, 127.45, 127.4, 126.7, 126.4; LCMS (EI): m/z 333 (MH+, 100%); Anal. Calcd for C26H20: C,93.94; H, 6.06. Found: C, 93.88; H, 6.09.

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

49
[ 18648-66-3 ]
[ 98-80-6 ]
[ 125643-81-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate; In water; toluene; at 90℃; for 6h;Inert atmosphere;	General procedure: A mixture of <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (1) (2.0 g, 5.97 mmol) and phenylboronic acid (873 mg, 7.16 mmol) was dissolved in toluene (15 mL) under argon atmosphere. Aqueous solution of K2CO3 (2 mL, 2 M), tricaprylylmethylammoniumchloride (Aliquat336) (3 drops) and Pd(PPh3)4 (10 mg) was added to the mixture. The reaction mixture was heated at 90C for 6 h. After being cooled to room temperature, distilled water (5 mL) was added and extracted with dichloromethane (310 mL). Organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, the residue was purified using column chromatography (silica gel, ethyl acetate/petroleum ether 5:95) afforded 2 (240 mg, 85%) as a white solid. Mp 97-98C; IR (KBr,cm-1): 3015, 1601, 1493; 1H NMR (300 MHz, CDCl3): delta 7.53 (d, 2H, J=7.5 Hz), 7.42-7.20 (m, 15H), 7.08 (d, 2H, J=7.5 Hz), 6.99 (s, 1H); 13C NMR (75 MHz, CDCl3): delta 143.2, 142.5, 140.4, 140.3, 139.1, 136.3, 130.0, 129.9, 128.7, 128.6, 128.1, 127.6, 127.5, 127.45, 127.4, 126.7, 126.4; LCMS (EI): m/z 333 (MH+, 100%); Anal. Calcd for C26H20: C,93.94; H, 6.06. Found: C, 93.88; H, 6.09.

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 740 - 747

50
[ 1227040-87-0 ]
[ 18648-66-3 ]
[ 1262330-95-9 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 1470 - 1478

51
[ 119-61-9 ]
[ 589-15-1 ]
[ 18648-66-3 ]

Yield	Reaction Conditions	Operation in experiment
90%		40.00 g of p-bromobenzyl bromide (0.16 mol) and 83.6 mL of triethyl phosphite (0.48 mol) were added to a solution of 500 mlThree bottles,Magnetic stirring and argon, oil bath heated at 150 C for 24 hours, cooled to room temperature,Get Ye Lide reagent.To the three-necked flask was added 450 ml of tetrahydrofuran (THF), 21.87 g of benzophenone (0.12 mol) and 40.39 g of potassium tert-butoxide (t-BuOK, 0.36 mol) were added and the mixture was stirred for 24 h. After the reaction was stopped, The solution was poured into water and extracted with a large amount of white precipitate. The precipitate was collected by extraction with a funnel, washed three times with ethanol and dried in a vacuum at 60C for 24 h to give Tri-Br as a white intermediate.

Reference： [1]Patent: CN104341311,2016,B .Location in patent: Paragraph 0028; 0029; 0030
[2]Chinese Journal of Chemistry,2015,vol. 33,p. 939 - 947

52
[ 18648-66-3 ]
9,9-dioctyl-2,7-bis(4-(2,2-diphenylvinyl)phenyl)-9H-fluorene [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2015,vol. 33,p. 939 - 947

53
[ 18648-66-3 ]
C₃₉H₂₇N₃O₂S [ No CAS ]