1357572-66-7|9-Bromo-7H-benzo[c]carbazole| Ambeed

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Quality Control of [ 1357572-66-7 ] Purity: 98% SDS Specification

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Product Details of [ 1357572-66-7 ]

CAS No. :	1357572-66-7
Formula :	C₁₆H₁₀BrN
M.W :	296.16
SMILES Code :	BrC1=CC2=C(C=C1)C3=C(C=CC4=CC=CC=C43)N2
MDL No. :	MFCD29918859
InChI Key :	ZXRPGNSDTBITJV-UHFFFAOYSA-N
Pubchem ID :	66585151

Safety of [ 1357572-66-7 ]

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 [ 1357572-66-7 ]

* 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 [ 1357572-66-7 ]

[ 1357572-66-7 ] Synthesis Path-Downstream 1~35

1
[ 13922-41-3 ]
[ 1357572-66-7 ]

References: [1]Patent: WO2013/32297,2013,A1 .
[2]Patent: WO2015/99486,2015,A1 .
[3]Dyes and Pigments,2015,vol. 123,p. 196 - 203.
[4]Patent: CN108822020,2018,A .
[5]Patent: CN109705100,2019,A .
[6]Patent: KR2021/8218,2021,A .

2
[ 591-50-4 ]
[ 1357572-66-7 ]
[ 1357572-67-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane;Reflux;	F2-3 (purchased) (20g, 67.53mmol), iodobenzene (16.53g, 81.03mmol), trans-1,2-cyclohexadiamine (7.71g, 8.11ml, 67.53mmol), CuI (12.86g, 67.53mmol), K3PO4 (42.96g, 202.59mmol) was put in a 500ml round bottom flask, dissolved in Dioxane (200ml), and stirred under reflux. After completion of the reaction, MC/H2O was extracted. The concentrated organic solvent was adsorbed on silica, followed by column purification and recrystallization. F2-2 (22.12g, 59.43mmol, 88%), D2 (17.76g, 71.31mmol), Pd(dba)2 (1.71g, 2.97mmol), Xphos (2.83g, 5.94mmol), NaOH (4.75g, 118.84mmol) in a 500ml round bottom flask, Dioxane (200ml) )/H2O (40ml) and stirred under reflux. After the reaction was completed, MC/H2O was extracted, followed by column purification and recrystallization. F2-1 (19.21g, 46.35mmol, 78%), Triphenylphosphine (24.31g, 92.70mmol) was dissolved in dichlorobenzene (DCB, dichlorobenzene) (200ml) and stirred under reflux. After the reaction was completed, DCB was sufficiently concentrated, followed by adsorption of silica, followed by column purification and recrystallization. F2 (9.22g, 24.10mmol, 52%) compound was obtained. (During the reaction, F14 was also produced.)
60%	With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; at 120.0℃; for 5h;	Compound 1-2 (20.0 g, 67.53 mmol), iodobenzene (15.0 mL, 135.06 mmol), CuT (12.0 g, 33.77 mmol), Cs2CO3 (66.0 g, 202.59 mmol), ethylenediamine (EDA) (2.0 mL, 33.77 mmol), and toluene (400.0 mL) were dissolved in a flask and the mixture was refluxed at 120 C for 5 hrs. After completing the reaction, the organic layer was extracted with EA and dried by removing the remaining moisture with MgSO4. The residue was separated via column chromatography to obtain compound 1-3 (15.0 g, 60%).
40%	With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; for 24h;	Preparation of compound 1-3 [122] After adding compound 1-2 (15.5 g, 52.3 mmol), iodobenzene (11.7 mL, 104.7 mmol), CuI (5.0 g, 26.2 mmol), ethylene diamine (EDA) (1.8 mL, 26.2 mmol), and Cs2CO3 (51.2 g, 157.0 mmol) to toluene (250 mL), the reaction mixture was stirred for one day. The reaction mixture was extracted with EA, was distillated under reduced pressure, and was separated through column (MC/Hex) to obtain compound 1-3 (7.9 g, 40 %).

References: [1]Patent: KR2020/72840,2020,A .Location in patent: Paragraph 0210-0212; 0222-0224.
[2]Patent: WO2015/99486,2015,A1 .Location in patent: Paragraph 153; 158; 159.
[3]Patent: WO2013/32297,2013,A1 .Location in patent: Paragraph 121; 122.

3
[ 1357572-65-6 ]
[ 1357572-66-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triphenylphosphine; In 1,2-dichloro-benzene; at 150.0℃; for 6h;	Compound 1-1 (70.0 g, 213.0 mmol), triphenylphosphine (140.0 g, 533.0 mmol), and dichlorobenzene (1.0 L) were dissolved in a flask and the mixture was refluxed at 150C for 6 hrs. After completing the reaction, the mixture was distilled and triturated with methanol (MeOH) to obtain compound 1-2 (40.0 g, 64 %).
61.4%	With triphenylphosphine; In 1,2-dichloro-benzene; at 180.0℃; for 16h;	Intermediate 1-1 (10 g, 0.031 mol), triphenylphosphine (19.98 g, 0.076 mol, sigma aldrich) was added to 300 mL of 1,2-dichlorobenzene and stirred under reflux at 180 C. for 16 hours to react. After completion of the reaction, the PPh3O precipitate was removed with petroleum ether, followed by column purification to give 10.6 g (yield 61.4%) of <Intermediate 1-2>.
52%	With triphenylphosphine; In 1,2-dichloro-benzene; for 5h;Reflux;	A mixture of 1-(4-bromo-2-nitrophenyl) naphthalene 1-1 (3.27 g, 10 mmol) and triphenylphosphine (5.25 g, 20 mmol) in 1,2-dichlorobenzene 20 mL was added into a round bottom flask, then heated to reflux for 5 h. After cooling to room temperature, the mixture was filtered under vacuum and washed with dichloromethane three times. The combined organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuum and the crude product was purified by SiO2 column chromatography, affording the yellow solid (1.53 g, 52%). IR (KBr, disk) ν 3404.88, 3061.90, 1584.84, 1529.22, 1467.48, 1433.99 cm-1. 1H NMR (400 MHz, CDCl3, δ): 8.69 (d, J = 8.4 Hz, 1H), 8.47 (s, 1H), 8.41 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 8.4 Hz, 1H), 7.89 (d, J = 8.8 Hz, 1H), 7.76-7.68 (m, 2H), 7.63 (d, J = 8.8 Hz, 1H), 7.50 (t, J = 7.6 Hz, 2H). HRMS (ESI, m/z): [M-H]+ calcd for: C16H9NS, 293.9918, found, 293.9920.

37%	With triethyl phosphite; In 1,2-dichloro-benzene; at 150.0℃; for 24h;	Preparation of compound 1-2 [120] After mixing compound 1-1 (47.5 g, 144.75 mmol), triethyl phosphite [P(OEt)3] (300 mL), and 1,2-dichlorobenzene (200 mL), the reaction mixture was stirred for one day at 150C. After terminating the reaction, the reaction mixture was concentrated under reduced pressure and was extracted with EA, and the organic layer was concentrated. The obtained organic layer was separated through column (MC/Hex) to obtain compound 1-2 (16 g, 37 %).
37%	With triethyl phosphite; In 1,2-dichloro-benzene; at 150.0℃; for 24h;Inert atmosphere;	Under the protection of argon, compound B1 (47.5 g, 144.75 mmol), triethyl phosphite (300 ml) and 1,2-dichlorobenzene (200 ml) were successively added to the reaction flask, and the reaction mixture was 150C Stir at for 1 day. After the reaction is over,The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate.The organic layer was concentrated and purified by column chromatography to afford compound B2 (16 g, 37%).
	With triethyl phosphite; at 150.0℃; for 24h;	40 g of the intermediate M11 was dissolved in 400 mL of triethyl phosphite and reacted at 150 C for 24 h.The solvent was distilled off under reduced pressure and the residue was purified to afford Intermediate M12.

References: [1]Patent: WO2015/99486,2015,A1 .Location in patent: Paragraph 153; 156; 157.
[2]Patent: KR2021/8218,2021,A .Location in patent: Paragraph 0111; 0116-0118.
[3]Dyes and Pigments,2015,vol. 123,p. 196 - 203.
[4]Patent: WO2013/32297,2013,A1 .Location in patent: Paragraph 119; 120.
[5]Patent: CN108822020,2018,A .Location in patent: Paragraph 0089; 0090; 0092.
[6]Patent: CN109705100,2019,A .Location in patent: Paragraph 0190; 0191; 0193.

4
[ 1357572-66-7 ]
[ 1426392-79-1 ]

References: [1]Patent: WO2013/32297,2013,A1 .

5
[ 1357572-66-7 ]
[ 1426392-80-4 ]

References: [1]Patent: WO2013/32297,2013,A1 .

6
[ 1357572-66-7 ]
[ 1426392-21-3 ]

References: [1]Patent: WO2013/32297,2013,A1 .

7
[ 1357572-66-7 ]
[ 1357572-68-9 ]

References: [1]Patent: WO2013/32297,2013,A1 .

8
[ 1357572-66-7 ]
[ 1426392-20-2 ]

References: [1]Patent: WO2013/32297,2013,A1 .

9
[ 3460-18-2 ]
[ 1357572-66-7 ]

References: [1]Patent: WO2013/32297,2013,A1 .
[2]Patent: WO2015/99486,2015,A1 .
[3]Dyes and Pigments,2015,vol. 123,p. 196 - 203.

10
[ 1357572-66-7 ]
C₂₈H₁₉ClN₂ [ No CAS ]