87220-68-6|9-Phenyl-9H-carbazole-3-carbaldehyde| Ambeed

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Quality Control of [ 87220-68-6 ] Purity: 98% GC SDS Specification

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Product Details of [ 87220-68-6 ]

CAS No. :	87220-68-6
Formula :	C₁₉H₁₃NO
M.W :	271.31
SMILES Code :	O=CC1=CC2=C(C=C1)N(C3=CC=CC=C3)C4=C2C=CC=C4
MDL No. :	MFCD19441087
InChI Key :	ITPJDBJBKAFUEG-UHFFFAOYSA-N
Pubchem ID :	18515440

Safety of [ 87220-68-6 ]

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

Application In Synthesis of [ 87220-68-6 ]

* 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 [ 87220-68-6 ]

[ 87220-68-6 ] Synthesis Path-Downstream 1~35

1
[ 4546-04-7 ]
[ 87220-68-6 ]
C₄₆H₃₂N₂ [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 8573 - 8576.

2
[ 1150-62-5 ]
[ 33513-42-7 ]
[ 87220-68-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With trichlorophosphate; at 0 - 90℃; for 8h;Inert atmosphere;	After dissolving 1eq (42.0g) of intermediate b-1 in 10eq (126g) of DMF and anhydrous, the temperature of the reactor is lowered to 0C, and 1.2eq (31.7g) of phosphoric chloride is slowly added. When the addition is complete, the reaction is completed by heating at 90C for 8 hours under reflux of nitrogen. When the reaction was completed, dichloromethane and distilled water were added for extraction, and the organic layer was dried over magnesium sulfate (MgSO4), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the product solid was recrystallized from dichloromethane and nucleic acid by silica gel column with hexane:dichloromethane=7:3 (v/v) to obtain intermediate b-2 (37.9g, Y=81%).
80%	With trichlorophosphate; at 0 - 20℃; for 12h;Inert atmosphere;	To a mixture of DMF (6.36 mL, 82.02 mmol) and 9-phenyl-9H-carbazole (2g, 8.22 mmol) was added drop wisely POCl3 (9.58 mL, 102.75 mmol) at0 C for over 30 min, then the reaction mixture was stirred at room temperaturefor 12 h and then poured into 100 mL ice water mixture. After filtration, thereaction mixture was extracted with CH2Cl2 then driedover anhydrous MgSO4. After removal of the solvent, the residue waspurified by column chromatography on silica gel using CH2Cl2/petroleum(1:2, v/v) to afford white powder. Yield: 80%. 1H NMR (500 MHz,DMSO, δ): 10.11 (s, 1H), 8.88 (s, 1H), 8.42 (d, J = 7.95 Hz, 1H), 7.99 (d, J= 8.56 Hz, 1H), 7.74 (t, J = 7.86 Hz,7.57 Hz, 2H), 7.68 (d, J = 7.27 Hz,2H), 7.63 (t, J = 7.31 Hz, 7.35 Hz,1H), 7.54 (t, J = 7.81 Hz, 7.50 Hz,1H), 7.49 (d, J = 8.55 Hz, 1H), 7.41(t, J = 7.22 Hz, 8.18 Hz, 2H).
79%		POCl3 (2.30 mL, 24.7 mmol) was added dropwise to DMF (14.6 mL,189.0 mmol) under stirring at 0 C. The resulting mixture was stirred at0 C for 4 h and then warmed to room temperature. To this mixture 9-phenyl-9H-carbazole 1 (5.0 g, 20.5 mmol) was added. The reactionmixture was heated to 90 C and stirred for 7 h. The solution was pouredinto an ice-bath, neutralized with sodium bicarbonate and extractedwith DCM (3 × 40 mL). The combined organic layer was dried withanhydrous Na2SO4 and concentrated under reduced pressure. The residueobtained was purified with column chromatography on 100: 200mesh silica gel by using 20% ethyl acetate in n-hexane as the eluent toafford compound 2 as a white solid (4.40 g, 79%).mp 108-110 C; 1H NMR (500 MHz, CDCl3): δ = 7.36-7.41 (distortedq, J = 8.0, 7.0 Hz, 2H), 7.43-7.49 (m, 2H), 7.52-7.56 (m, 3H), 7.65 (t, J= 8.0, 7.5 Hz, 2H), 7.94-7.96 (dd, J = 9.0, 1.5 Hz, 1H), 8.21 (d, J = 8.0Hz, 1H), 8.68 (s, 1H), 10.12 (s, 1H); 13C NMR (125 MHz, CDCl3): δ =110.09, 110.40, 120.65, 121.18, 123.22, 123.58, 123.82, 126.98,127.18, 127.44, 128.32, 129.45, 130.11, 136.71, 141.87, 144.50,191.71; ESI-MS: m/z 272.02 [M + H]+.

75%		DMF (43.4 mL) is added to a round-bottomed flask and nitrogen is added and the reaction temperature is adjusted to 0 & lt; 0 & gt; C. Thenphosphoryl chloride (32 g, 200 mmol) is slowly added dropwise and the temperature is raised to room temperature and then stirred for 1 hour. The reaction temperature is adjusted again to 0 C and a solution of 9-phenyl carbazole (2.92 g, 120 mmol) in 1,2-dichloroethane (52 mL) is addeddropwise over 1 hour. After the reaction was completed, the reaction mixture was extracted with ice water and CH 2 Cl 2 , and the obtained organic layer was separatedwith water and subjected to column chromatography using MgSO 4, and recrystallized from ethanol and hexane to obtain 31.4 g 75%) of 3-aldehyde-9-phenyl carbazole (intermediate A).
45%	With trichlorophosphate; In 1,2-dichloro-ethane; for 12h;Reflux;	Add in dry reaction flaskPOCl3 (0.91 mL, 10 mmol) andDMF (1.5 mL, 20 mmol), stirred at room temperature for 1 h,10 mL of 1,2-dichloroethane was added to obtain reaction solution A.Reaction A was transferred to a constant pressure dropping funnel and added dropwise to 80 mL containing9-Phenyl-9H-carbazole (2.43 g, 10 mmol) in 1,2-dichloroethane.After the addition was complete, the reaction was heated at reflux and stirred for 12 h. Cool to room temperatureThe reaction was slowly poured into 1 L of vigorously stirred deionized water and extracted with DCM.Several layers were combined and washed three times with deionized water. The resulting organic phase was dried over anhydrous MgSO4.After drying, the solid was filtered off, and the resulting filtrate was concentrated using ethyl acetate and petroleum ether as eluents.Column chromatography yields the product as a white solid9-Phenyl-9H-carbazole-3-carbaldehyde (1.22 g, 4.5 mmol), yield 45%.
		Phosphorus oxychloride (9.18 mL) was added dropwise to distilled DMF (10 mL) and the mixture of 9-phenyl-9H-carbazole (11.03 g, 45.4 mmol) and DMF (25 mL) were also added dropwise to phosphorus oxychloride/DMF mixture at room temperature. The mixture constant stirring continuously for 2 h at 80C and left at room temperature, after pouring ice water and then neutralized with NaOH up to 7-8 pH, after slowly forming brown precipitate. It has been filtered using methanol and purified by column chromatography (ethyl acetate/hexane). In addition, 9-phenyl-9H-carbazole-2-carbaldehyde (11.53 g) and ethanol (125 mL) were incorporated into a 250 mL flask and then 10 g BrCl was progressively added to the mixture at 75 C (0.5 drop/s) until the reaction was completed. A brown solid (6-bromo-9-phenyl-9H-carbazole-2-carbaldyde) formed and recrystallized by anhydrous ethanol.

References: [1]Patent: KR102129510,2020,B1 .Location in patent: Paragraph 0270-0271; 0273.
[2]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[3]Journal of Materials Chemistry C,2015,vol. 3,p. 9469 - 9478.
[4]Journal of Materials Chemistry C,2019,vol. 7,p. 9671 - 9677.
[5]Organic electronics,2021,vol. 92.
[6]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[7]Patent: TWI580673,2017,B .Location in patent: Page/Page column 44.
[8]Macromolecules,2003,vol. 36,p. 3457 - 3464.
[9]Molecular Crystals and Liquid Crystals,2011,vol. 536,p. 182 - 191.
[10]Journal of Materials Chemistry,2002,vol. 12,p. 3469 - 3474.
[11]Patent: CN104163835,2017,B .Location in patent: Paragraph 0049.
[12]Journal of Materials Chemistry C,2013,vol. 1,p. 4171 - 4179.
[13]Dyes and Pigments,2016,vol. 129,p. 1 - 8.
[14]Organic electronics,2021,vol. 92.
[15]Asian Journal of Chemistry,2021,vol. 33,p. 1541 - 1550.

3
[ 530-47-2 ]
[ 87220-68-6 ]
9-phenyl-9H-carbazole-3-carbaldehyde N,N-diphenylhydrazone [ No CAS ]

References: [1]Journal of Materials Chemistry,2002,vol. 12,p. 3469 - 3474.

4
[ 618-40-6 ]
[ 87220-68-6 ]
9-phenyl-9H-carbazole-3-carbaldehyde N-methyl-N-phenylhydrazone [ No CAS ]

References: [1]Journal of Materials Chemistry,2002,vol. 12,p. 3469 - 3474.

5
[ 87220-68-6 ]
[ 540473-55-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With pyridine; hydroxylamine hydrochloride; acetic acid; at 140℃; for 5h;	To the reaction mixture were added 3-aldehyde-9-phenyl carbazole (31.4 g, 116 mmol), hydroxylamine hydrochloride (10 g, 140.4 mmol), acetic acid(25.1 g, 418 mmol), pyridine (16.72 g, 209 mmol) 83 mL) are added in this order to the reaction flask, and then the mixture is stirred at 140 DEG C for 5 hours. After the reaction was completed, the reaction mixture was extracted with water and CH 2 Cl 2 , and the obtained organic layer was separated byusing MgSO 4 and column chromatography, and recrystallized from ethanol and hexane to obtain 23 g (74%) of 3-cyano-9 -phenylcarbazole(intermediate B).

References: [1]Journal of Materials Chemistry C,2019,vol. 7,p. 9671 - 9677.
[2]Patent: TWI580673,2017,B .Location in patent: Page/Page column 44; 45.
[3]Macromolecules,2003,vol. 36,p. 3457 - 3464.

6
[ 87220-68-6 ]
[ 540473-57-2 ]

References: [1]Macromolecules,2003,vol. 36,p. 3457 - 3464.

7
[ 87220-68-6 ]
[ 540473-61-8 ]

References: [1]Macromolecules,2003,vol. 36,p. 3457 - 3464.

8
[ 100-63-0 ]
[ 87220-68-6 ]
[ 1357516-22-3 ]

References: [1]Molecular Crystals and Liquid Crystals,2011,vol. 536,p. 182 - 191.

9
[ 87220-68-6 ]
[ 1357351-42-8 ]

References: [1]Molecular Crystals and Liquid Crystals,2011,vol. 536,p. 182 - 191.

10
[ 87220-68-6 ]
[ 1357516-26-7 ]

References: [1]Molecular Crystals and Liquid Crystals,2011,vol. 536,p. 182 - 191.

11
[ 87220-68-6 ]
[ 1357516-27-8 ]

References: [1]Molecular Crystals and Liquid Crystals,2011,vol. 536,p. 182 - 191.

12
[ 137-07-5 ]
[ 87220-68-6 ]
[ 664995-51-1 ]

References: [1]Journal of Materials Chemistry C,2013,vol. 1,p. 4171 - 4179.

13
[ 86-74-8 ]
[ 87220-68-6 ]

References: [1]Journal of Materials Chemistry C,2013,vol. 1,p. 4171 - 4179.
[2]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[3]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[4]Journal of Materials Chemistry C,2015,vol. 3,p. 9469 - 9478.
[5]Dyes and Pigments,2016,vol. 129,p. 1 - 8.
[6]Patent: TWI580673,2017,B .
[7]Patent: CN104163835,2017,B .
[8]Patent: KR102129510,2020,B1 .
[9]Organic electronics,2021,vol. 92.

14
[ 108-86-1 ]
[ 87220-68-6 ]

References: [1]Journal of Materials Chemistry C,2013,vol. 1,p. 4171 - 4179.
[2]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[3]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[4]Journal of Materials Chemistry C,2015,vol. 3,p. 9469 - 9478.
[5]Patent: TWI580673,2017,B .
[6]Patent: KR102129510,2020,B1 .

15
[ 1150-62-5 ]
[ 4885-02-3 ]
[ 87220-68-6 ]

References: [1]Photochemical and Photobiological Sciences,2013,vol. 12,p. 284 - 297.

16
[ 87220-68-6 ]
[ 354820-63-6 ]
C₃₄H₃₃N₃O₅ [ No CAS ]

References: [1]Photochemical and Photobiological Sciences,2013,vol. 12,p. 284 - 297.

17
[ 62-53-3 ]
[ 84-11-7 ]
[ 87220-68-6 ]
1-phenyl-2-(9-phenyl-9H-carbazol-3-yl)-1H-phenanthro[9,10-d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With ammonium acetate; acetic acid; for 2h;Inert atmosphere; Reflux;	Synthesis of 1-phenyl-2-(9-phenyl-9H-carbazol-3-yl)-1H-phenanthro[9,10-d]imidazole (M3): a mixture of <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (500.00 mg, 1.85 mmol), phenanthrene-9,10-dione (460.50 mg, 2.21 mmol), aniline (0.50 g), ammonium acetate (0.60 g, 8.00 mmol), and acetic acid (10 mL) were refluxed under nitrogen in an oil bath. After 2 h, the mixture was cooled and filtered. The solid product was washed with an acetic acid/water mixture (1:1, 150 mL) and water. It was then purified by chromatography using CH2Cl2/petroleum ether (1:1) as eluent to obtain the product as white powder. Yield: 80%. 1H NMR (500 MHz, DMSO, δ): 8.96 (d, J = 7.98 Hz, 1H), 8.91 (d, J = 8.67 Hz, 1H), 8.76 (d, J = 7.28 Hz, 1H), 8.35 (s, 1H), 8.09 (d, J = 7.53 Hz, 1H), 7.81-7.76 (m, 4H), 7.73-7.68 (m, 6H), 7.64 (d, J = 7.08 Hz, 2H), 7.58 (t, J = 7.69 Hz, 7.08 Hz, 2H), 7.48 (t, J = 7.08 Hz, 7.00 Hz, 1H), 7.39-7.31 (m, 4H), 7.16 (d, J = 7.94 Hz, 1H); MALDI-TOF (m/z): [M+] calcd for C39H25N3:535.64; Found: 535.4. Anal. calcd for C39H25N3: C 87.45, H 4.70, N 7.84; Found: C 87.28, H 4.66, N 7.77.
80%	With ammonium acetate; acetic acid; at 120℃; for 2h;Inert atmosphere;	A mixture of <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (500.00 mg, 1.85 mmol),phenanthrene-9,10-dione (460.50 mg, 2.21 mmol), aniline(0.50 g), ammoniumacetate (0.60 g, 8.00 mmol), and aceticacid (10 mL) were refluxed under nitrogen in an oil bath.After 2 h, the mixture was cooled and filtered. The solidproduct was washed with an acetic acid/water mixture(1:1, 150 mL) and water. It was then purified by chromatographyusing CH2Cl2/petroleum ether (1:1) as eluent toobtain the product as white powder. Yield: 80%. 1H NMR(500 MHz, DMSO, d): 8.96 (d, J = 7.98 Hz, 1H), 8.91 (d,J = 8.67 Hz, 1H), 8.76 (d, J = 7.28 Hz, 1H), 8.35 (s, 1H), 8.09(d, J = 7.53 Hz, 1H), 7.81-7.76 (m, 4H), 7.73-7.68 (m, 6H),7.64 (d, J = 7.08 Hz, 2H), 7.58 (t, J = 7.69 Hz, 7.08 Hz, 2H),7.48 (t, J = 7.08 Hz, 7.00 Hz, 1H), 7.39-7.31 (m, 4H), 7.16(d, J = 7.94 Hz, 1H); MALDI-TOF (m/z): [M+] calcd forC39H25N3:535.64; Found: 535.4. Anal. calcd for C39H25N3:C 87.45, H 4.70, N 7.84; Found: C 87.28, H 4.66, N 7.77.

References: [1]Organic electronics,2014,vol. 15,p. 2667 - 2676.
[2]Organic electronics,2014,vol. 15,p. 2667 - 2676.

18
[ 87220-68-6 ]
3-(1-(4-bromophenyl)-1H-benzo[d]imidazol-2-yl)-9-phenyl-9H-carbazole [ No CAS ]