57103-20-5|3,6-Dibromo-9-phenyl-9H-carbazole| Ambeed

Structure of 57103-20-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size

Price

VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock

{[ item.pr_size ]}

Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

Quality Control of [ 57103-20-5 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 57103-20-5 ]

CAS No. :	57103-20-5
Formula :	C₁₈H₁₁Br₂N
M.W :	401.10
SMILES Code :	BrC1=CC=C2N(C3=CC=C(Br)C=C3C2=C1)C1=CC=CC=C1
MDL No. :	MFCD08276338
InChI Key :	JBWRZTKHMKVFMQ-UHFFFAOYSA-N
Pubchem ID :	11025791

Safety of [ 57103-20-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319-H413
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 57103-20-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	19
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	96.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	4.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.69
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	6.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.31
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	5.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.95
Solubility	0.000045 mg/ml ; 0.000000112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.28
Solubility	0.000213 mg/ml ; 0.000000531 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-8.28
Solubility	0.00000213 mg/ml ; 0.0000000053 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.22 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.81

Application In Synthesis of [ 57103-20-5 ]

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

Downstream synthetic route of [ 57103-20-5 ]

[ 57103-20-5 ] Synthesis Path-Downstream 1~55

1
[ 1150-62-5 ]
[ 57103-20-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide; at 20℃; for 12h;Inert atmosphere;	To a solution of 9-phenyl-9H-carbazole (2.04 g, 8.05 mmol) in CCl3(15 mL) keeping in dark place, NBS (3.29 g, 18.49 mmol) was added three times.The mixture was stirred for 12 h at room temperature. Then, water was added tothe mixture to give a white precipitate. After filtration and drying, theobtained white solid was recrystallized from petroleum. Yield: 100%.
92%	With N-Bromosuccinimide; In ethyl acetate; at 20℃; for 52h;	First, into a 200-mL Mayer flask were put 3.7 g (15 mmol) of 9-phenyl-9H-carbazole, 5.4 g (30 mmol) of N-bromosuccinimide (abbreviation: NBS), and75 mL of ethyl acetate. At room temperature, this solution was stirred in the air for 52 hours. Then, water was added thereto and this mixture was furtherstirred. An aqueous layer of the mixture was subjected to extraction with ethyl acetate three times. The extracted solution and an organic layer werecombined, the mixture was washed with water and saturated saline, and then magnesium sulfate was added thereto. The obtained mixture was gravityfilteredand the filtrate was concentrated, so that 5.5 g of the target white powder was obtained in a yield of 92%.
90.3%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 - 25℃; for 24.5h;Inert atmosphere;	Under nitrogen protection,N-phenylcarbazole (48.6 g, 0.2 mol) was dissolved in 500 mL DMF (N, N-dimethylformamide) in a 1 L three-necked flask,NBS (N-bromosuccinimide, 78.3 g, 0.44 mol) was slowly added to the reaction system at a temperature of 20 to 25 C,0.5h plus completed.The reaction system was stirred at 20-25 C for 24 hours.After completion of the reaction to the reaction systemAn aqueous solution of sodium sulfite (500 mL, 0.05 mol / L) was added,Quenching reaction,Filter cake,After washing with deionized water,Crystallization is carried out with toluene or absolute ethanol,To give a white solid,Namely the intermediate C01-a,The yield was 90.3%.

90%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 - 25℃; for 24.5h;Inert atmosphere;	Under nitrogen protection,N-phenylcarbazole (48.6 g, 0.2 mol) was dissolved in 500 mL of DMF (N, N-dimethylformamide) in a 1 L three-necked flask,To the reaction system was slowly added NBS (N-bromosuccinimide, 78.3 g, 0.44 mol) as a solid at a controlled temperature of 20-25 C,0.5h plus completed.The reaction system was incubated at 20-25 C for 24 hours with stirring.After completion of the reaction, an aqueous solution of sodium sulfite (500 mL, 0.05 mol / L) was added to the reaction system,The reaction mixture was quenched and the filter cake was suction filtered to obtain a cake. The residue was washed with deionized water and then crystallized from toluene or absolute ethanol to give a white solid, which was 3,6-dibromo-N-phenylcarbazole in 90% yield.
87%	With N-Bromosuccinimide; In chloroform; at 20℃; for 3h;	Preparation of Structural Formula 1B; The Structural Formula 1A (13.2 g, 54.3 mmol) was dissolved in chloroform (300 ml), and N-bromo succinimide (20.3 g, 114.0 mmol)) was added thereto, and agitated for 3 hours at normal temperature. Distilled water was put into the reaction solution, the termination of the reaction was carried out, and the organic material layer was extracted. The reaction solution was concentrated, and recrystallized with EtOH to obtain the Structural Formula 1B (18.9 g, yield 87 %). MS: [M+H]+ = 402
87.8%	With bromine; acetic acid; In dichloromethane; at 20℃;Cooling with ice;	0.1640 mol of N-phenyl-9H-carbazole was charged into a 2000 ml three-necked flask, washed with 320 ml of acetic acid and 960 ml of dichlorMethane dissolved, placed in ice water bath; slowly dropping 0.3280mol liquid bromine, room temperature reaction overnight,The reaction solution was neutralized with 1.5 L of 1 mol / L aqueous sodium hydroxide solution to the remaining liquid bromine, and the organic phase was separated to obtain an organic phase,Respectively, washed three times with water, liquid to take organic phase, spin dry,Washed with 300 ml PE (60-90), suction filtered, vacuum dried at 55 C,To give the product 3,6-dibromo-9-phenylcarbazole 0.1440 mol, 87.8% yield.
79.04%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 25℃; for 5h;	N-bromosuccinimide (15.00 g, 84 mmol, 2.05 eq) is dissolved in 30 ml of dimethylformamide and then slowly added to a flask in which 30 ml of 9-phenyl-9Hcarbazole (10 g, 41 mmol, 1.0 eq) is dissolved in 30 ml of dimethylformamide. After 5 hours of reaction, the reaction product was precipitated with 200 ml of distilled water, filtered and dried to obtain 13.03 g (yield: 79.04%) of the target compound.
64%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	Example 3 Synthesis of Carbozole-Based (2-Arm) Fluorescent Molecular Rotor (0310) RRN 38Preparation of 3,6-dibromo-9-phenyl-9H-carbazole (0311) 9-phenyl-9H-carbazole (0.3 g, 1.23 mmol, 1 eq.) was dissolved in DMF. N-Bromosuccinimide (0.44 g, 2.47 mmol, 2 eq.) was then added slowly and the resultant mixture was allowed to stir at room temperature overnight. The reaction mixture was then poured into brine and extracted with DCM. The organic extracts were then dried with Na2SO4 and concentrated. Crude product was then re-precipitated with methanol and THF gave white solids as 3,6-dibromo-9-phenyl-9H-carbazole (0.32 g, 64%). (0312) 1H NMR (CDCl3, 400 MHz) delta 7.24 (s, 1H), 7.48-7.52 (m, 5H), 7.59-7.64 (m, 2H), 8.20 (d, 2H, J=2.0 Hz). 13C NMR (100 MHz, CDCl3) delta 140.1, 137.0, 130.3, 129.5, 128.3, 127.2, 124.1, 123.4, 113.2, 111.7.
56.9%	With bromine; In dichloromethane; acetic acid;	Example 11 3,6-Dibromo-9-phenylcarbazole 9-Phenylcarbazole (2.000 g, 8.220 mmol) was suspended in 15 mL glacial acetic acid in a 125 ml 3-neck round bottom flask equipped with an addition funnel and a condenser. The reaction was under N2 blanket. Bromine (0.880 ml, 17.262 mmol) mixed with 15 mL glacial acetic acid was added dropwise and stirred at 0 C. Upon completion of the addition the reaction was allowed to warm to room temperature and stirred for about 5 hours. Dichloromethane (100 mL) was added, and stirred vigorously until all the solids dissolved. Two phases were separated in the separation funnel. The acid layer was extracted twice with 50 mL dichloromethane. The organic layers were combined and washed with brine until the pH=7. The organic layers were dried over MgSO4 and filtered. Solvent was removed under vacuum. The crude product was then recrystallized from dichloromethane. Yield: 56.9%. M.P.: 162.7-163.6 C.

References: [1]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[2]Tetrahedron,1998,vol. 54,p. 12707 - 12714.
[3]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148.
[4]Patent: JP2015/63518,2015,A .Location in patent: Paragraph 0253; 0254.
[5]Patent: CN105906612,2016,A .Location in patent: Paragraph 0051; 0052.
[6]Patent: CN105175405,2017,B .Location in patent: Paragraph 0039-0041.
[7]Patent: EP2343277,2011,A2 .Location in patent: Page/Page column 32.
[8]Patent: CN104650044,2017,B .Location in patent: Paragraph 0035; 0038.
[9]Synlett,2006,p. 2841 - 2845.
[10]Macromolecules,2005,vol. 38,p. 4970 - 4976.
[11]Patent: KR101638767,2016,B1 .Location in patent: Paragraph 0109-0112.
[12]Patent: US2016/195519,2016,A1 .Location in patent: Paragraph 0310; 0311; 0312.
[13]Patent: US2006/83945,2006,A1 .
[14]Journal of Materials Chemistry,2011,vol. 21,p. 4918 - 4926.
[15]Journal of Chemical Research,2008,p. 137 - 140.
[16]Chemistry - A European Journal,2008,vol. 14,p. 4731 - 4740.
[17]Journal of Nanoscience and Nanotechnology,2010,vol. 10,p. 6811 - 6814.
[18]Journal of the Chinese Chemical Society,2012,vol. 59,p. 331 - 337.
[19]Journal of Materials Chemistry,2012,vol. 22,p. 4527 - 4534.
[20]Journal of the Chinese Chemical Society,2013,vol. 60,p. 579 - 589.
[21]Chemistry - A European Journal,2016,vol. 22,p. 7468 - 7478.

2
[ 51545-42-7 ]
[ 57103-20-5 ]
N-phenyl-3,6-dimethylcarbazole [ No CAS ]

References: [1]Tetrahedron,1998,vol. 54,p. 12707 - 12714.

3
[ 1826-67-1 ]
[ 57103-20-5 ]
9-phenyl-3,6-divinyl-9H-carbazole [ No CAS ]

References: [1]Tetrahedron,1998,vol. 54,p. 12707 - 12714.

4
[ 57103-20-5 ]
phenylmagnesium halide [ No CAS ]
3,6,9-triphenylcarbazole [ No CAS ]

References: [1]Tetrahedron,1998,vol. 54,p. 12707 - 12714.

5
[ 57103-20-5 ]
[ 436800-48-5 ]
N,N'-bis(9-ethyl-9H-carbazol-3-yl)-9-N,N'-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 9404 - 9411.

6
[ 57103-20-5 ]
[ 373390-07-9 ]
N,N'-bis(9,9-diethyl-9H-fluoren-2-yl)-9,N,N'-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 9404 - 9411.

7
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148.
[2]Organic Letters,2006,vol. 8,p. 5033 - 5036.
[3]Tetrahedron Letters,2005,vol. 46,p. 855 - 858.

8
[ 1150-62-5 ]
[ 1153-85-1 ]
[ 57103-20-5 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 1123 - 1139.

9
[ 90-30-2 ]
[ 57103-20-5 ]
N3,N6-di(naphthalene-1-yl)-N3,N6,9-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In tetrahydrofuran; toluene; at 100℃; for 36h;	Procedure for Synthesis of Compounds 7c. A mixture of3,6-dibromo-9H-carbazole 4 (1.0 g, 2.5 mmol), N-phenyl-naphthalen-1-amine 5 (1.6 g, 7.3 mmol), Pd(OAc)2(0.15 g, 0.67 mmol), t-Bu3P 50percent in toluene (0.5 mL,2.2 mmol), and NaOtBu 2 M in THF (5.0 mL, 47.4 mmol)in 100 mL of dry toluene was stirred at 100C for 36 h. After completion of the reaction, the mixture was extractedwith dichloromethane. The organic layer was separated,dried over magnesium sulfate, ltered, and evaporated. Theresidue was puried by silica gel column chromatographyusing n-hexane: dichloromethane as the eluent to givedesigned compounds 7c.N3,N6-di(naphthalene-1-yl)-N3,N6,9-triphenyl-9H-carba-zole-3,6-diamine (7c). Yield: 78percent; yellow solid; 1H NMR(500 MHz, CDCl3) delta8.08?8.06 (d, J = 8.0Hz, 2H),7.89?7.88 (d, J = 8.0Hz, 2H), 7.8 (s, 2H), 7.74?7.73 (d,J = 8.0Hz, 2H), 7.60?7.55 (q, J1 = 7.5Hz, J2 = 15.0Hz,4H), 7.47?7.44 (m, 5H), 7.37?7.34 (q, J1 = 7.5Hz,J2 = 15.0 Hz, 4H), 7.31?7.25 (m, 4H), 7.16?7.13 (t,J = 8Hz, 4H), 6.89?6.84 (q, J1 = 8.0Hz, J2 = 15.0Hz, 6H);13C NMR (125 MHz, CDCl3) delta183.6, 179.2, 171.3, 168.4,160.1, 159.7, 141.5, 135.3, 129.0, 128.4, 128.2, 127.5,127.2, 126.8, 126.0, 125.0, 124.6, 120.5, 119.7, 110.7; GC-MS: 668.23 for C50H35N3 [M + H+].

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 9404 - 9411.
[2]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 1710 - 1716.

10
[ 57103-20-5 ]
[ 250597-29-6 ]
polymer, alternating, M_n 5800 Da, M_w/M_n 1.3; monomer(s): 3,6-dibromo-9-phenylcarbazole; 9,9-dihexyl-2,7-bis(1,3,2-dioxaborinan-2-yl)fluorene [ No CAS ]

References: [1]Macromolecules,2005,vol. 38,p. 4970 - 4976.

11
[ 854952-58-2 ]
[ 57103-20-5 ]
[ 918137-84-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Inert atmosphere; Heating;	In a three-necked flask equipped with a stirrer 2.50 g (6.23 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (compound a), 1.79 g (6.23 mmol) of 9-phenylcarbazole-3-boronic acid (compound b), 41.6 ml of 2 M potassium carbonate (K2CO3) aqueous solution (83.2 mmol of potassium carbonate) and 125 ml of tetrahydrofuran (THF) were added and nitrogen bubbling was carried out for 1 hour. 350 mg (0.31 mmol) of tetrakis (triphenylphosphine)palladium (Pd (PPh 3) 4) was added thereto and heated and stirred overnight. The reaction solution was returned to room temperature and the solvent was distilled off. After adding dichloromethane to the residue and redissolving it, and then washed with a saturated saline solution. Anhydrous magnesium sulfate was added to the organic layer, and the organic layer was dried and filtered. After concentrating the filtrate, silica gel column chromatography (dichloromethane: hexane = 1: 4) was carried out, a target compound c was obtained in a yield of 1.32 g (0.24 mmol) in a yield of 38percent.
32%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere;	100 g (348 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid was dissolved in 1.3 L of tetrahydrofuran (THF) in a nitrogen environment, 168 g (418 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> and 4.02 g, 3.48 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. 102 g (696 mmol) of potassium carbonate saturated in water was added thereto, and the mixture was heated and refluxed at 80 °C for 16 hours. When the reaction was terminated, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound I-28 (62.8 g, 32 percent). HRMS (70 eV, EI+): m/z calcd for C36H23BrN2: 562.1045, found: 562.1. Elemental Analysis: C, 77 percent; H, 4 percent

References: [1]Journal of Materials Chemistry C,2013,vol. 1,p. 8177 - 8185.
[2]Synlett,2006,p. 2841 - 2845.
[3]Patent: JP2017/145198,2017,A .Location in patent: Paragraph 0043-0044.
[4]Patent: EP2889296,2015,A1 .Location in patent: Paragraph 0265-0268.

12
[ 591-50-4 ]
potassium hexacyanoferrate (II) [ No CAS ]
[ 57103-20-5 ]

References: [1]Synlett,2006,p. 2841 - 2845.

13
[ 86-74-8 ]
sodium-salt of/the/ benzoylamino-methanesulfonic acid [ No CAS ]
[ 57103-20-5 ]

References: [1]Synlett,2006,p. 2841 - 2845.

14
[ 57103-20-5 ]
[ 918137-86-7 ]

References: [1]Synlett,2006,p. 2841 - 2845.

15
[ 57103-20-5 ]
[ 915224-45-2 ]

References: [1]Organic Letters,2006,vol. 8,p. 5033 - 5036.

16
[ 57103-20-5 ]
C₆₀H₄₅N [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 5033 - 5036.

17
[ 57103-20-5 ]
(2-{6-[2-(hydroxy-di-p-tolyl-methyl)-phenyl]-9-phenyl-9H-carbazol-3-yl}-phenyl)-di-p-tolyl-methanol [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 5033 - 5036.

18
[ 57103-20-5 ]
3,6-bis-[2-(4-tert-butyl-phenyl)-pyrimidin-5-yl]-9-phenyl-9H-carbazole [ No CAS ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 855 - 858.

19
[ 57103-20-5 ]
[ 57103-21-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-iodo-succinimide; acetic acid; at 20℃;	[0102] 24.3 g (100 mmol) N-phenyl-<strong>[57103-20-5]3,6-dibromocarbazole</strong> in a glacial acetic acid (500 mL) solution was added with 44.9 g (200 mmol) of N-iodine succinimide to be stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture until the liquid properties became neutral. The mixture was filtrated and the obtained solid was washed with water and dried to give N-phenyl-3,6-diiodinecarbazole (hereinafter, shown as PhI2Cz) with a yield of 85percent. [0103] By using the obtained PhI2Cz, a coupling reaction was performed with carbazole in the similar manner as described in the synthesis of N-ethyl-3,6-di(N-carbazolyl)carbazole to give the compound in the title, N-phenyl-3,6-di(N-carbazolyl)carbazole as a beige solid (yield: 85percent). NMR data are shown in FIG. 15 (1H NMR) and FIG. 16 (13C NMR). [0104] 1H NMR(300 MHz, CDCl3) delta 7.20-7.80(m, 21H), 8.15(d, J=7.8 Hz, 4H), 8.27(s, 2H). [0105] 13C NMR(75.5 MHz, CDCl3) delta 109.7, 111.3, 119.7, 120.3, 123.2, 123.9, 125.9, 126.3, 127.2, 128.2, 130.2, 130.4, 137.1, 140.7, 141.8. [0106] It had the melting point at 283° C and showed the sublimation point at 410° C under normal pressure. Formation of a uniform film over a substrate by a vacuum evaporation method was confirmed. Absorption maximum was at 341 nm in methanol and 344 nm for the evaporated film. It was fluorescent, showing the maximum of fluorescence at 435 nm in methanol and 409 nm for the evaporated film. The HOMO level was at -5.64 eV, and the LUMO level was at -2.33 eV. The absorption spectra for the methanol solution and evaporated film are shown in FIG. 10. The respective fluorescent spectrum and excitation spectrum are shown in FIG. 11.

References: [1]Patent: US2005/31899,2005,A1 .Location in patent: Page/Page column 18.

20
P(t-Bu)3 [ No CAS ]
[ 65838-93-9 ]
[ 57103-20-5 ]
N,N'-dipyren-1-yl-9,N,N'-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Pd(dba)2; In diethyl ether; hexane; dichloromethane; toluene;	3,6-Dibromo-N-phenyl-carbazole (1 mmol), phenyl-pyren-1-yl-amine (2.1 mmol), Pd(dba)2 (0.04 mmol), P(t-Bu)3 (0.04-0.06 mmol), sodium t-butoxide (0.288 g, 3 mmol), and toluene (20 ml) were mixed together and heated at 80° C. for 4-6 hours. The reaction was quenched with water (30 ml) and the organic layer was taken into 100 ml diethyl ether, washed with brine solution and dried over MgSO4. Evaporation of the solvent under vacuum resulted in a yellow solid that was adsorbed in silica gel and purified by column chromatography using dichloromethane/hexane mixture as eluant to produce Compound 1 (94percent). 1H NMR(300 MHz, CDCl3, TMS): delta[ppm]=6.78-6.87(m, 6 H), 7.08(t, 4 H, J=7.6 Hz), 7.25(d, 6 H, J=5.8 Hz), 7.36-7.42(m, 1 H), 7.51-7.54(m, 2 H), 7.76-7.80(m, 4 H), 7.86(d, 2 H, J=9.1 Hz), 7.93(t, 2 H, 7.4 Hz), 7.98(s, 4 H), 8.03-8.10(m, 6 H), 8.19(d, 2 H, J=9.3 Hz); MS (FAB): m/z 825(M+, 100percent); elemental analyses: calculated: C 90.15, H 4.76, N 5.09; found: C 90.34, H 4.60, N 5.01.

References: [1]Patent: US2002/107405,2002,A1 .

21
[ 109-72-8 ]
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In tetrahydrofuran; water; acetone;	Part B: Synthesis of 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole A 2 L flask was charged with 600 mL dry THF and 3,6-dibromo-9-phenylcarbazole (60 g, 0.15 mole). This was cooled to -78° C. with an acetone-dry ice bath. n-Butyllithium (138 mL of a 2.5M solution in hexanes, 0.34 mole) was added drop-wise via syringe. The reaction was stirred for 20 minutes and then warmed to -50° C. The temperature was reduced to -78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (64 g, 0.34 mole) added via syringe at such a rate as to maintain the temperature below -60° C. The temperature was maintained at -78° C. for two hours and then poured into an aqueous solution of ammonium acetate (90 g in 2100 mL water). The layers were phase separated and the aqueous phase extracted with methyl-t-butyl ether (2200 mL). The combined organic phase and extracts were washed with brine (2200 mL) and dried over magnesium sulfate. Concentration and re-crystallization of the solid obtained from acetone gave pure 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole. This compound can be used to modify the hole transport properties of for example the compound of Example 17. To do this 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is used in place of 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in Example 17.

References: [1]Patent: US7271406,2007,B2 .

22
[ 591-50-4 ]
[ 6825-20-3 ]
[ 57103-20-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone); at 170℃; for 20h;	Synthesis of Intermediate E; 3.25 g (10.0 mmol) of 3, 6-dibromocarbazole, 10.2 g (50.0 mmole) iodobenzene, 190 mg (1.0 mmole) of Cul, 132 mg (0.5 mmole) of 18-C-6, 2.76 g (20.0mmole) of K2CO3 were dissolved in 50 mL of DMPU, and stirred at 170°C for 20 hours. The mixture was cooled to room temperature and 50 mL of diethylether was added thereto. Then the mixture was washed with plenty of water and ammonium hydroxide solution. A collected organic layer was dried over MgSO4 to evaporate the solvent. The residue was purified using silica gel column chromatography to obtain 3.40 g of white solid Intermediate E (Yield: 85 percent). (NMR (CDCl3, 400MHz) delta (ppm) 7.92 (m, 2H), 7.55-7.47 (m, 6H), 7.36-7.16 (m, 3H); 13C NMR (CDCl3, 100MHz) delta (ppm) 142.6, 137.6, 130.2, 129.8, 127.4, 127.0, 122.8, 122.5, 115.3, 111.3).
75%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	To a round bottom flask Sub 2-1-6 (6.5g, 20mmol), Sub 2-1-2-1 (4.1g, 20mmol),Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol ), NaOt-Bu (5.8g, 60mmol), were addedto toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100 ° C.The organic layer was dried and the ether was extracted with water over MgSO4 andconcentrated and to the resulting organic silicagel column and recrystallized from a Sub2-1-7-1 6.0g (yield: 75percent) was obtained.
3.27 g	With palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate; In toluene;	2.5 g (14.9 mmol) ofcarbazole was used (utilized) to perform an NI3S bromination to synthesize 2,5-dibromocar- bazole. Then, the 2,5-dibromocarbazole and iodinated phenyl were used (utilized) to synthesize 3.72 g (9.28 mmol) of Intermediate E through a buchwald reaction.

References: [1]Patent: EP1921082,2008,A1 .Location in patent: Page/Page column 35-36.
[2]Journal of Nanoscience and Nanotechnology,2011,vol. 11,p. 1373 - 1376.
[3]Patent: KR2015/93995,2015,A .Location in patent: Paragraph 0149; 0153; 0182-0184.
[4]RSC Advances,2015,vol. 5,p. 51512 - 51523.
[5]Patent: KR2015/144421,2015,A .Location in patent: Paragraph 0317; 0318; 0319.

23
[ 76-86-8 ]
[ 57103-20-5 ]
[ 1097245-00-5 ]

Yield	Reaction Conditions	Operation in experiment
55%		Synthesis of Intermediate F; 4.01 g (10 mmol) of Intermediate E was dissolved in 20 mL of THF, and 4.6mL (12.0 mmol) of 2.6M n-butyllithium (in Hexane) was added thereto at -78°C for 10 minutes. 3.83 g (13.0 mmol) of chlorotriphenylsilane dissolved in 20 mL of THF was gradually added thereto at -78 for 20 minutes, and the mixture was stirred at room temperature for 17 hours. 50 mL of water was added to the mixture and the mixture was extracted twice with 50 mL of diethylether. A collected organic layer was dried over MgSO4 to evaporate the solvent. The residue was purified using silica gel column chromatography to obtain 3.19 g of white solid Intermediate F (Yield: 55percent). (NMR (CDCl3, 400MHz) delta (ppm) 8.28-8.21 (m, 3H), 8.14 (d, 2H), 7.86-7.14 (m, 21 H); 13C NMR (CDCl3, 100MHz) delta (ppm) 143.1, 137.9, 136.4, 134.4, 133.9, 133.7, 129.8, 129.5, 129.0, 128.0, 127.9, 127.5, 126.9, 124.9, 123.9, 123.1, 118.3, 111.2, 109.7, 107.6).
		To 4.58 g of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> as intermediate of preparation example 2 was added to 60 mL of tetrahydrofuran, and the temperature was adjusted to -78 degree C. Subsequently, 1.26 mL of butyllithium was slowly added dropwise. The mixture was stirred for 2 hours while maintaining its temperature, and 3.71 g of chlorotriphenylsilane was slowly added dropwise, after which the temperature of the mixture was raised to room temperature. After completion of the reaction, triethylamine and methanol were added at a ratio of 1:10 and the reaction mixture was stirred and extracted, followed by drying the solvent. The resulting solid was filtered and purified, yielding 3-bromo-9-phenyl-6-(triphenylsilyl)-9-carbazole as white intermediate.

References: [1]Patent: EP1921082,2008,A1 .Location in patent: Page/Page column 36.
[2]Patent: JP5663566,2015,B2 .Location in patent: Paragraph 0161.

24
[ 57103-20-5 ]
[ 1135916-40-3 ]

References: [1]Journal of Chemical Research,2008,p. 137 - 140.

25
[ 68-12-2 ]
[ 57103-20-5 ]
[ 145771-93-3 ]

Yield	Reaction Conditions	Operation in experiment
89%		0.0996 mol of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> was charged into a three-necked flask and dissolved in 500 ml of THF (except water)Vacuum - nitrogen three times, dry ice - acetone bath cooling, slowly dropping 0.2490mol n-butyl lithium,Low temperature reaction for one hour; slowly dropping 0.5478molDMF, low temperature reaction for one hour, continue room temperature reaction overnight. The reaction solution was added with water to terminate the reaction, and the appropriate amount of 2 mol / L dilute hydrochloric acid was added to the solution.Add 400ml methylene chloride separation, take dichloromethane phase, spin-dried silica gel column,The eluent was DCM: PE (60-90) = 2: 3 to give the product 9-phenylcarbazole-3,6-dicarboxylate 0.0886 mol,Yield 89%.
20%	With n-butyllithium; In tetrahydrofuran; at -78℃; for 7h;Inert atmosphere;	n-butyllithium (2.5 M, 5.5 mL, 13.75 mmol) was slowly added to asolution of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> (1.05 g, 2.618 mmol) in THF (100mL) at -78 C. The reaction was kept at this temperature for 3 h, and then DMF(2.10 mL) was added drop-wise. The resulting mixture was further stirred for 4h more at -78 C. Water was added, and the reaction mixture was extracted withCH2Cl2 then dried over anhydrous MgSO4. Afterremoval of the solvent, the residue was purified by column chromatography onsilica gel using CH2Cl2/petroleum (1:5, v/v) to affordwhite powder. Yield: 20%. 1H NMR (500 MHz, DMSO, delta): 10.14 (s, 2H),9.02 (s, 2H), 8.07 (d, J = 8.65 Hz,2H), 7.77 (t, J = 7.94 Hz, 7.23 Hz,2H), 7.71 (d, J = 7.64 Hz, 2H), 7.67(t, J = 7.23 Hz, 7.23 Hz, 1H), 7.53(d, J = 8.35 Hz, 2H).

References: [1]Patent: CN104650044,2017,B .Location in patent: Paragraph 0035; 0036; 0039.
[2]Chemistry - A European Journal,2008,vol. 14,p. 4731 - 4740.
[3]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[4]Organic electronics,2014,vol. 15,p. 2667 - 2676.

26
[ 1036378-83-2 ]
[ 57103-20-5 ]
[ 1201649-79-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 20h;Reflux; Inert atmosphere;	1.20 g (3.0 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong>, 2.35 g (6.6 mmol) of TPDOB, 8.0 ml of 2 M potassium carbonate aqueous solution, 60 ml of toluene and 30 ml of ethanol and nitrogen bubbling was carried out for 1 hour .40.21 g (0.18 mmol) of Pd (PPh 3) was added and refluxed for 4 hours.The organic layer was extracted with toluene and washed with saturated brine.The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated and purified by silica gel column chromatography (developing solvent: hexane / toluene = 5/1 => 3/1) to obtain a white solid.Confirmation of the target substance was carried out by 1 H-NMR, MS. (Yield 1.27 g, yield 60percent)

References: [1]Chemical Communications,2009,p. 6655 - 6657.
[2]Patent: JP5674266,2015,B2 .Location in patent: Paragraph 0045; 0047.

27
[ 1189047-28-6 ]
[ 57103-20-5 ]
[ 1189047-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 15h;	Example 5 Synthesis of Compound 11 In a 1,000-mL three-necked flask were placed 11.0 g (38.3 millimoles) of 2-carbazolylphenylboronic acid, 6.0 g (15.0 millimoles) of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong>, and 1.6 g (1.4 millimoles) of tetrakis(triphenylphosphine)palladium(0), then 100 mL of ethanol and 200 mL of toluene were added, and the mixture was stirred. Thereafter, a solution of 15.0 g (142.0 millimoles) of sodium carbonate in 200 mL of water was thrown into the flask. The mixture was then heated to 80°C and stirred for 15 hours. The reaction solution was cooled to room temperature, transferred to a 1,000-mL separatory funnel, and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 200 mL of water and then dehydrated over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The reaction mixture thus obtained was purified by recrystallization from THF and methanol to yield 5.1 g of Compound 11 as a white solid; EI-MS, 726 (M+1); melting point, 275°C; glass transition temperature, 143°C.

References: [1]Patent: EP2272828,2011,A1 .Location in patent: Page/Page column 18.

28
[ 2372-33-0 ]
[ 57103-20-5 ]
[ 1097244-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane;	Example 4e Synthesis of 3,6-bis[(4-methoxyphenyl)dimethylsilyl]-9-phenylcarbazole A solution of 9-phenyl-3,6-dibromo-9H-carbazole (1.6 g, 1 eq) in dry THF (20 ml) at -78° C. under argon is admixed slowly with n-butyllithium (1.6 M in hexane, 6.1 ml, 2.5 eq) and stirred at -78° C. for 1 h. After adding a solution of 4-methoxyphenyl-dimethylchlorosilane (2.4 g, 3.1 eq) in dry THF (10 ml) at -78° C., the mixture is warmed to room temperature with stirring overnight. Excess butyllithium is hydrolyzed with saturated ammonium chloride solution. The precipitated product is filtered off and washed thoroughly with CH2Cl2. The combined methylene chloride filtrates are extracted with water and concentrated to dryness. The residue is purified by column chromatography (silica gel, hexane/ethyl acetate). Yield 40percent. MALDI-MS: m/z=571. HPLC: 99percent purity.

References: [1]Patent: US2011/31477,2011,A1 .

29
[ 57103-20-5 ]
3,6-bis(dimethylpentafluorophenylsilyl)-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With n-butyllithium; In tetrahydrofuran; hexane;	Example 4j Synthesis of 3,6-bis(dimethylpentafluorophenylsilyl)-9-phenylcarbazole Reaction Procedure: A solution of 9-phenyl-3,6-dibromo-9H-carbazole (3.1 g, 1 eq) in dry THF (150 ml) is admixed slowly at -78° C. under argon with n-butyllithium (1.6 M in hexane, 12.2 ml, 2.5 eq) and stirred at -78° C. for 1 h. After a solution of flophemesyl chloride (6.1 g, 3.0 eq) in dry THF (10 ml) has been added at -78° C., the mixture is warmed to room temperature overnight with stirring. Excess butyllithium is hydrolyzed with saturated ammonium chloride solution. The precipitated product is filtered off and washed thoroughly with CH2Cl2. Column chromatography (C18-SiO2, MeCN) gives the product. Yield 65percent. 1H NMR (CDCl3, 400 MHz):

References: [1]Patent: US2011/31477,2011,A1 .

30
[ 76-86-8 ]
[ 57103-20-5 ]
[ 754231-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane;	Example 4b Synthesis of 9-phenyl-3,6-bis(triphenylsilyl)-carbazole A solution of 9-phenyl-3,6-dibromo-9H-carbazole (6.0 g, 1 eq) in dry THF (500 ml) at -78° C. under argon is admixed slowly with n-butyllithium (1.6 M in hexane, 28.2 ml, 3.0 eq) and stirred at -78° C. for 1 h. After adding a solution of chlorotriphenylsilane (13.5 g, 3.0 eq) in dry THF (100 ml) at -78° C., the mixture is warmed to room temperature with stirring overnight. Excess butyllithium is hydrolyzed with saturated ammonium chloride solution. The precipitated product is filtered off and washed thoroughly with CH2Cl2. The product precipitates out of the combined CH2Cl2 filtrates. Yield: 40percent. If the product does not precipitate out, the combined CH2Cl2 filtrates are concentrated to dryness. Recrystallization with ethyl acetate gives the product. 1H NMR (CDCl3, 400 MHz): delta=7.35 (m, 12H), 7.45 (m, 9H), 7.52-7.6 (m, 18H), 8.2 (s, 2H).

References: [1]Patent: US2011/31477,2011,A1 .

31
[ 732306-23-9 ]
[ 57103-20-5 ]
[ 1097244-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane;	Example 4d Synthesis of 3,6-bis[(3,5-bis(trifluoromethyl)phenyl)dimethylsilyl]-9-phenyl-carbazole A solution of 9-phenyl-3,6-dibromo-9H-carbazole (1.3 g, 1 eq) in dry THF (50 ml) at -78° C. under argon is admixed slowly with n-butyllithium (1.6 M in hexane, 5.1 ml, 2.5 eq) and stirred at -78° C. for 1 h. After adding a solution of 3,5-bis(trifluoromethyl)phenyldimethylchlorosilane (2.5 g, 2.5 eq) in dry THF (20 ml) at -78° C., the mixture is warmed to room temperature with stirring overnight. Excess butyllithium is hydrolyzed with saturated ammonium chloride solution. The precipitated product is filtered off and washed thoroughly with CH2Cl2. The combined methylene chloride filtrates are extracted with water and concentrated to dryness. The residue is purified by column chromatography (silica gel, methylene chloride/cyclohexane). Yield 60percent. 1H NMR (CDCl3, 400 MHz): delta=0.7 (s, 12H), 7.4-7.7 (m, 9H), 7.8 (s, 2H), 8.0 (s, 4H), 8.3 (s, 2H).

References: [1]Patent: US2011/31477,2011,A1 .

32
[ 57103-20-5 ]
[ 74-88-4 ]
[ 1221237-81-5 ]

Yield	Reaction Conditions	Operation in experiment
71%		Preparation of Structural Formula 1C; The Structural Formula 1B (18.9 g, 47.1 mmol)) was dissolved in 200 ml of tetrahydrofurane anhydride, and cooled to -78ºC, and 2.5 M n-butyl lithium (18.8 ml, 47.1 mmol) was slowly added thereto, and agitated for 1 hour. After iodomethane (3.2 ml, 51.8 mmol) was added to the reaction solution, the temperature was slowly increased to normal temperature, it was agitated for 2 hours, and the ammonium chloride aqueous solution was added thereto to finish the reaction, thereby extracting the organic layer. The reaction solution was concentrated, and recrystallized with petroleum ether to obtain the Structural Formula 1C (11.2 g, yield 71 %). MS: [M+H]-= 337

References: [1]Patent: EP2343277,2011,A2 .Location in patent: Page/Page column 32-33.

33
[ 86-74-8 ]
[ 57103-20-5 ]

References: [1]Patent: EP2343277,2011,A2 .
[2]Journal of Materials Chemistry,2011,vol. 21,p. 4918 - 4926.
[3]Journal of the Chinese Chemical Society,2012,vol. 59,p. 331 - 337.
[4]Journal of Materials Chemistry,2012,vol. 22,p. 4527 - 4534.
[5]Journal of the Chinese Chemical Society,2013,vol. 60,p. 579 - 589.
[6]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[7]Patent: KR2015/144421,2015,A .
[8]Patent: CN104650044,2017,B .

34
[ 591-50-4 ]
[ 57103-20-5 ]

References: [1]Patent: EP2343277,2011,A2 .
[2]Journal of Materials Chemistry,2011,vol. 21,p. 4918 - 4926.
[3]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148.
[4]Journal of the Chinese Chemical Society,2012,vol. 59,p. 331 - 337.
[5]Journal of Materials Chemistry,2012,vol. 22,p. 4527 - 4534.
[6]Journal of the Chinese Chemical Society,2013,vol. 60,p. 579 - 589.
[7]Patent: CN104650044,2017,B .

35
[ 57103-20-5 ]
[ 1221237-01-9 ]

References: [1]Patent: EP2343277,2011,A2 .

36
[ 57103-20-5 ]
[ 1221237-21-3 ]

References: [1]Patent: EP2343277,2011,A2 .

37
[ 57103-20-5 ]
[ 1221238-01-2 ]

References: [1]Patent: EP2343277,2011,A2 .

38
[ 37500-95-1 ]
[ 57103-20-5 ]
[ 1256943-89-1 ]

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 4918 - 4926.

39
[ 86-74-8 ]
[ 57103-20-5 ]
[ 211685-96-0 ]

Yield	Reaction Conditions	Operation in experiment
38%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; at 180℃; for 3.5h;Inert atmosphere;	First, in a 200-mL three-neck flask, a mixture including 2.8 g (7.0 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>, 2.7 g (16 mmol) of carbazole, 1.9 g (10 mmol) of copper(I) iodide, 2.5 g (10 mmol) of 18-crown-6-ether, 2.8 g (20 mmol) of potassium carbonate, and 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (abbreviation: DMPU) was stirred under a nitrogen atmosphere at 180° C. for 3.5 hours to cause a reaction. (0319) After the reaction, water was added to this reaction mixture and filtration was performed. Methanol was added to an obtained residue and ultrasonic cleaning was performed. The residue was collected and dried; then, toluene was added and the mixture was stirred while being heated, and then filtered. An obtained filtrate was purified by silica gel column chromatography. An obtained fraction was recrystallized, so that an objective substance was obtained as 1.5 g of white powder at a yield of 38percent. The above reaction is shown in Scheme (b-1) below. (0320) compound obtained by the above synthesis method are shown below. The results showed that the above-described PhCzGI (abbreviation) was obtained. (0323) 1H NMR data of the obtained substance are as follows: (0324) 1H NMR (CDCl3, 300 MHz): delta (ppm)=7.26-7.32 (m, 4H), 7.40 (d, J=3.3 Hz, 8H), 7.57-7.74 (m, 9H), 8.16 (d, J=7.5 Hz, 4H), 8.28 (d, J=1.5 Hz, 2H).

References: [1]Journal of Materials Chemistry,2011,vol. 21,p. 4918 - 4926.
[2]Patent: US9029558,2015,B2 .Location in patent: Page/Page column 56.

40
[ 57103-20-5 ]
[ 111-27-3 ]
[ 1235572-98-1 ]

References: [1]Journal of Nanoscience and Nanotechnology,2010,vol. 10,p. 6811 - 6814.

41
[ 67492-50-6 ]
[ 57103-20-5 ]
[ 1350856-49-3 ]

References: [1]Dyes and Pigments,2012,vol. 92,p. 891 - 896.

42
[ 870774-25-7 ]
[ 57103-20-5 ]
[ 1365608-78-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 85℃; for 13h;Inert atmosphere;	Example 7; In this example, an example in which 3,6-bis-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: NP2PC) represented by Structural Formula (112) in Embodiment 1 is manufactured will be described. In a 200-mL three-neck flask, a mixture of 2.0 g (5.0 mmol) of 3,6-dibromo-9-phenyl-9H-carbazole, 2.7 g (11 mmol) of 4-(1-naphthyl)phenylboronic acid, 100 mg (0.5 mmol) of palladium(II) acetate, 41 mg (0.1 mmol) of tri(o-tolyl)phosphine, 20 mL of toluene, 2 mL of ethanol, and 30 mL of a potassium carbonate aqueous solution (2 mol/L) was deaerated while being stirred under reduced pressure, and then heated and stirred in a nitrogen atmosphere at 85° C. for 13 hours to be reacted.After the reaction, 150 mL of toluene was added to the reaction mixture solution, and an organic layer of the mixture solution was filtrated through Florisil, alumina, and Celite. The obtained filtrate was washed with water, and magnesium sulfate was added thereto to adsorb moisture. This suspension was filtrated to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. At this time, a mixed solvent of toluene and hexane (toluene:hexane=1:4) was used as a developing solvent for the chromatography. The obtained fraction was concentrated, and acetone and methanol were added thereto. The mixture was irradiated with ultrasonic waves and then recrystallized to give 2.2 g of white powder that was an objective substance in a yield of 69percent. The reaction scheme of the synthesis method is shown in (F7-1). The Rf values of the objective substance and 3,6-dibromo-9-phenyl-9H-carbazole were respectively 0.25 and 0.58 which were obtained by silica gel thin layer chromatography (TLC) (with a developing solvent containing ethyl acetate and hexane in a 1:10 ratio).The obtained compound was examined by a nuclear magnetic resonance (NMR) method. The measurement data are shown below.1H NMR (CDCl3, 300 MHz): delta (ppm)=7.45-7.68 (m, 19H), 8.02 (dd, J=2.1 Hz, 9.0 Hz, 2H), 7.87-7.95 (m, 8H), 8.05 (d, J=7.8 Hz, 2H), 8.55 (d, J=1.5 Hz, 2H).FIGS. 26A and 26B are 1H NMR charts. Note that FIG. 26B is a chart showing an enlarged part of FIG. 26A in the range of 7.0 ppm to 9.0 ppm. The measurement results confirmed that NP2PC that was the objective substance was able to be obtained.FIG. 27A shows an absorption spectrum of NP2PC in a toluene solution of NP2PC, and FIG. 27B shows an emission spectrum thereof. FIG. 28A shows an absorption spectrum of a thin film of NP2PC, and FIG. 28B shows an emission spectrum thereof. The absorption spectrum was measured with a UV-visible spectrophotometer (V550, produced by JASCO Corporation). The emission spectrum was measured with a fluorescence spectrophotometer (FS920, produced by Hamamatsu Photonics Corporation). The measurements were performed with samples prepared in such a manner that the solution was put in a quartz cell while the thin film was obtained by evaporation onto a quartz substrate. FIG. 27A show the absorption spectrum of NP2PC in the solution of NP2PC which was obtained by subtracting the absorption spectra of the quartz cell and toluene put therein, and FIG. 28A shows the absorption spectrum of the thin film which was obtained by subtracting the absorption spectrum of the quartz substrate. In FIGS. 27A and 27B and FIGS. 28A and 28B, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). In the case of the toluene solution, the absorption peak was observed at around 314 nm, and the maximum emission wavelength was 392 nm (excitation wavelength: 310 nm). In the case of the thin film, the absorption peak was observed at around 314 nm, and the maximum emission wavelength was 404 nm (excitation wavelength: 315 nm).The absorption spectrum showed that NP2PC described in this example is a material having weak absorption of light in the visible region. In addition, the emission spectrum shows that NP2PC exhibits blue-violet emission.Further, the thermophysical property was examined with a differential scanning calorimeter (DSC). The measurement result showed that the melting point is 269° C. In addition, glass transition and a crystallization peak were not observed; thus, it was found that NP2PC is a substance which is difficult to be crystallized.

References: [1]Patent: US2012/77987,2012,A1 .Location in patent: Page/Page column 51-52.

43
[ 100124-06-9 ]
[ 6163-58-2 ]
[ 57103-20-5 ]
[ 1364890-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In methanol; ethanol; hexane; water; acetone; toluene;	Synthesis Method of 3,6-di(dibenzofuran-4-yl)-9-phenyl-9H-carbazole (abbreviated as DBF2PC-II)To a 200-mL three-neck flask were added 2.0 g (5.0 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>, 3.2 g (11 mmol) of dibenzofuran-4-boronic acid, 10 mg (0.1 mmol) of palladium(II) acetate, 30 mg (0.1 mmol) of tris(o-tolyl)phosphine, 50 mL of toluene, 5 mL of ethanol, and 7.5 mL of a 2 mol/L aqueous potassium carbonate solution.This mixture was degassed while being stirred under reduced pressure, and then heated and stirred at 90° C. for 6.5 hours under a nitrogen stream to be reacted.After the reaction, 250 mL of toluene was added to this reaction mixture and the mixture was heated.The mixture was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135) in this order to give a filtrate.The resulting filtrate was purified by silica gel column chromatography (a developing solvent in which the toluene/hexane ratio was 1:3).The obtained fraction was concentrated, acetone, methanol, and water were added thereto, and the mixture was irradiated with ultrasonic waves.Then, acetone and methanol were added to the obtained precipitate and the mixture was irradiated with ultrasonic waves, filtrated, washed, and dried.Thereby, 2.8 g of a target substance, white powder, was obtained in 69percent yield.A reaction scheme of the above synthesis method is illustrated in the following (E-1).The Rf values of the white powder obtained through the reaction and <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> were respectively 0.32 and 0.55, which were found by silica gel thin layer chromatography (TLC) (a developing solvent in which the ethyl acetate/hexane ratio was 1:10).The white powder obtained by the step 1 was subjected to nuclear magnetic resonance (NMR) spectroscopy.The measurement data are shown below.show the 1H NMR charts.Note that is an enlarged chart of .By the measurement results, it was confirmed that the white powder obtained by the step 1 was DBF2PC-II, which is represented by the structural formula (208).1H NMR (CDCl3, 300 M Hz): delta (ppm)=7.37 (dt, J=7.8 Hz, J=1.2 Hz, 2H), 7.44-7.56 (m, 5H), 7.60-7.69 (m, 8H), 7.75 (dd, J=7.2 Hz, J=1.5 Hz, 2H), 7.95 (dd, J=7.8 Hz, J=1.5 Hz, 2H), 8.00-8.04 (m, 4H), 8.75 (d, J=1.5 Hz, 2H).

References: [1]Patent: US2012/91887,2012,A1 .

44
[ 108847-20-7 ]
[ 6163-58-2 ]
[ 57103-20-5 ]
[ 1364890-79-8 ]

Yield	Reaction Conditions	Operation in experiment
47%	palladium diacetate; In ethanol; hexane; acetone; toluene;	Step 1:Synthesis of 3,6-di-(dibenzothiophen-4-yl)-9-phenyl-9H-carbazole (abbreviated as DBT2PC-II)To a 200-mL three-neck flask were added 2.0 g (5.0 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>, 3.2 g (11 mmol) of dibenzothiophene-4-boronic acid, 10 mg (0.1 mmol) of palladium(II) acetate, 30 mg (0.1 mmol) of tri(ortho-tolyl)phosphine, 50 mL of toluene, 5 mL of ethanol, and 7.5 mL of a 2 mol/L aqueous potassium carbonate solution.This mixture was degassed while being stirred under reduced pressure, and then heated and stirred at 90° C. for 6 hours in a nitrogen atmosphere to be reacted.After the reaction, this reaction mixture solution was cooled to room temperature, and then filtered to give a residue while being washed with water, ethanol, toluene, and hexane in this order.The residue was purified by silica gel column chromatography (a developing solvent in which the toluene/hexane ratio was 1:3).The fraction thus obtained was concentrated, acetone and ethanol were added thereto, and the mixture was irradiated with ultrasonic waves.Then, recrystallization gave 1.4 g of a white powder in 47percent yield.The synthesis scheme of Step 1 is shown in (A-1).The obtained white powder was subjected to nuclear magnetic resonance (NMR) spectroscopy.The measurement data are shown below.1H NMR (CDCl3, 300 MHz): delta=7.44-7.70 (m, 15H), 7.82-7.86 (m, 4H), 8.15-8.22 (m, 4H), 8.57 (d, J=1.5 Hz, 2H)

References: [1]Patent: US2012/91887,2012,A1 .

45
[ 952514-79-3 ]
[ 57103-20-5 ]
[ 1258780-50-5 ]

References: [1]Journal of Nanoscience and Nanotechnology,2011,vol. 11,p. 1373 - 1376.

46
[ 1227040-87-0 ]
[ 57103-20-5 ]
[ 1361123-19-4 ]