18992-65-9|2,7-Dimethyl-9H-carbazole| Ambeed

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Quality Control of [ 18992-65-9 ] Purity: 98% SDS Specification

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Product Details of [ 18992-65-9 ]

CAS No. :	18992-65-9
Formula :	C₁₄H₁₃N
M.W :	195.26
SMILES Code :	CC1=CC2=C(C=C1)C3=C(C=C(C)C=C3)N2
MDL No. :	MFCD01851748
InChI Key :	ABYRPCUQHCOXMX-UHFFFAOYSA-N
Pubchem ID :	181098

Safety of [ 18992-65-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 18992-65-9 ]

* 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 [ 18992-65-9 ]

[ 18992-65-9 ] Synthesis Path-Downstream 1~28

1
[ 59517-21-4 ]
[ 18992-65-9 ]

References: [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 709 - 714.

3
diazotized 2.2'-diamino-4.4'-dimethyl-diphenyl [ No CAS ]
[ 18992-65-9 ]

References: [1]Chemische Berichte,1901,vol. 34,p. 3335.

4
[ 53356-70-0 ]
[ 18992-65-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 24.0h;	The intermediate step of Int.-1 15g 100ml dichlorobenzene were mixed and stirred and 86.5g of triphenylphosphine was added, heated to 180 deg.] C for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, to the residue was 100ml of petroleum ether was added, heated to boiling, filtered hot and the filter cake was washed with petroleum ether, and dried in vacuo to give 11.5g of 2,7-dimethyl-carbazole Int.-2, a yellow solid, yield 89%
89%	With triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 24.0h;	15 g of the intermediate of the previous step Int. -1 and 100 ml of dichlorobenzene were mixed, and 86.5 g of triphenylphosphine was added under stirring.Heating to 180 C for 24 hours, cooling to room temperature,The concentrate was dried under reduced pressure and 100 ml of petroleum ether was added to the residue. The mixture was heated to boiling and filtered while hot,The filter cake was washed with petroleum ether and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography,Yielding 11.5 g of 2, 7-dimethylcarbazole Int.-2 as a yellow solid in 89% yield.
89%	With triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 24.0h;	15 g of the first step intermediate Int.-1 and 100 ml of dichlorobenzene were mixed, 86.5 g of triphenylphosphine was added under stirring, and the mixture was heated to 180 C for 24 hours.Cool to room temperature, concentrate to dryness under reduced pressure, add 100 ml of petroleum ether to the residue, warm to boiling, filter while hot, and wash the filter cake with petroleum ether.The filtrate was concentrated to dryness under reduced pressure and the residue was purified using silica gel column.11.5 g of 2,7-dimethylcarbazole Int.-2 were obtained as a yellow solid, yield 89%.

87%	With triethyl phosphite; at 100℃; for 12.0h;Inert atmosphere;	Under the protection of nitrogen, 60 g of 2-nitro-4,4'-dimethylbiphenyl and 300 ml of triethyl phosphite were added to a 500 ml three-necked flask. The temperature was raised to 100 C and the reaction was stopped for 12 hours. The reaction was cooled down. To room temperature to obtain solution C; Solution C was poured into 5L of water, and solid precipitated. Vacuum filtration gave a crude yellow 2,7-dimethylcarbazole. The crude product was washed with 200-400 mesh silica gel as a stationary phase, petroleum ether / ethyl acetate (volume ratio 20: 1, 15: 1, 10: 1) as eluent, and washed through the column in order to obtain an off-white powder.45g of 2,7-dimethylcarbazole,The purity was 99% and the yield was 87% (total yield 84%).
24%	With triethyl phosphite; for 16.0h;Heating / reflux;	Synthesis example 2 2,7-dimethylcarbazole 4.3 g (19 mmol) 4,4'-dimethyl-2-nitro-1,1'-biphenyl in 15 ml triethylphosphite is refluxed during 16 hours in argon atmosphere. The mixture was allowed to cool to room temperature, upon which the product precipitated. Filtration and washing with methanol gave 0.88 g (24 %) of the white solid. 1H NMR (DMSO-d6): delta 11.0 (s, 1H), 7.92 (d, J=8 Hz, 2H), 7.25 (s, J=1.5 Hz, 2H), 6.96 (d, J=1.5 Hz, J=8 Hz, 2H), 2.41 (s, 6H). 13C NMR (DMSO-d6): delta 140, 134, 120, 120, 119, 111, 21. mp: 292 C.

References: [1]Patent: CN105481755,2016,A .Location in patent: Paragraph 0079; 0080; 0081.
[2]Patent: CN105399748,2016,A .Location in patent: Paragraph 0072; 0077-0079.
[3]Patent: CN108440537,2018,A .Location in patent: Paragraph 0079; 0085; 0086; 0087.
[4]Patent: CN110437134,2019,A .Location in patent: Paragraph 0028; 0031-0033; 0036-0038; 0041-0042.
[5]Patent: EP1838671,2008,B1 .Location in patent: Page/Page column 8.

5
[ 18992-65-9 ]
[ 890079-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20℃;	Synthesis example 3 3,6-dibromo-<strong>[18992-65-9]2,7-dimethylcarbazole</strong> In a flask, covered with aluminum foil, a stirred solution of 0.5 g (2.6 mmol) <strong>[18992-65-9]2,7-dimethylcarbazole</strong> in 10 ml tetrahydrofuran was cooled to 0 C. 0.86 g (4.8 mmol) N-bromosuccinimide was added in small portions. The mixture was allowed to warm to room temperature overnight. The THF was evaporated and the solid was used without further purification. 1H NMR (DMSO-d6): delta 11.38 (s, 1H), 8.40 (s, 1H), 7.46 (s, 1H), 2.41 (s, 6H).

References: [1]Patent: EP1838671,2008,B1 .Location in patent: Page/Page column 8.

6
[ 626-13-1 ]
[ 18992-65-9 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 4720 - 4726.

7
[ 613-33-2 ]
[ 18992-65-9 ]

References: [1]Patent: CN105481755,2016,A .

8
[ 18992-65-9 ]
3,6-diiodo-2,7-dimethyl-9-phenylcarbazole [ No CAS ]

References: [1]Patent: CN105481755,2016,A .
[2]Patent: CN105399748,2016,A .

9
[ 18992-65-9 ]
C₃₂H₂₃Br₂N [ No CAS ]

References: [1]Patent: CN105481755,2016,A .

10
[ 18992-65-9 ]
C₅₈H₄₁NO₂ [ No CAS ]

References: [1]Patent: CN105481755,2016,A .

11
[ 108-86-1 ]
[ 18992-65-9 ]
2,7-dimethyl-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In toluene; for 24.0h;Inert atmosphere; Reflux;	The intermediate step 2g of Int.-3,3.2g bromobenzene, 4.2g of anhydrous potassium carbonate, 19mg of cuprous iodide and 40ml of toluene were mixed with dry, deoxygenated vacuum pressure for 10 minutes, under a nitrogen blanket , tetramethylethylenediamine was added 13.6mg, heated at reflux for 24 hours, cooled to room temperature, suction filtered, the filter cake washed with ethyl acetate, the filtrate was diluted to 50ml of water, the organic phase was separated, concentrated under reduced pressure dryness and the residue was separated by silica gel column eluting with petroleum ether to give 2.3g of Int.-3, a white solid, yield 82%.
82%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In toluene; for 24.0h;Inert atmosphere; Reflux;	2g of the intermediate intermediate Int.-2, 3. 2 g of bromobenzene,4. 2 g of anhydrous potassium carbonate,19 mg of cuprous iodide were dissolved in 40 ml of dry toluene was mixed and vacuum deaerated under reduced pressure for 10 minutes. Under a nitrogen atmosphere,13.6 mg of tetramethylethylenediamine was added and the mixture was heated to reflux for 24 hours, cooled to room temperature. The filter cake was washed with ethyl acetate and the filtrate was diluted with 50 ml of water. The organic phase was separated and concentrated to dryness under reduced pressure.The residue was purified by silica gel column eluting with petroleum ether to give 2.3 g of Int-3 as a white solid in 82% yield.
82%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In toluene; for 24.0h;Inert atmosphere; Reflux;	2g of the second step of the intermediate Int.-2, 3.2g of bromobenzene, 4.2g of anhydrous potassium carbonate,19 mg of cuprous iodide was mixed with 40 ml of dried toluene and deoxygenated under vacuum for 10 minutes.Under nitrogen protection, 13.6 mg of tetramethylethylenediamine was added, and the reaction was refluxed for 24 hours.After cooling to room temperature, suction filtration, the filter cake was washed with ethyl acetate, diluted with 50 ml of water, and the organic phase was separated.Concentrated to dryness under reduced pressure, the residue was isolated and purified by a silica gel column, eluting with petroleum ether,2.3 g of Int.-3 were obtained as a white solid with a yield of 82%.

References: [1]Patent: CN105481755,2016,A .Location in patent: Paragraph 0082; 0083; 0084.
[2]Patent: CN105399748,2016,A .Location in patent: Paragraph 0072; 0080-0082.
[3]Patent: CN108440537,2018,A .Location in patent: Paragraph 0079; 0088; 0089; 0090.

12
[ 18992-65-9 ]
C₃₂H₂₃N₃ [ No CAS ]

References: [1]Patent: CN105399748,2016,A .

13
[ 18992-65-9 ]
C₄₄H₃₁N₃ [ No CAS ]

References: [1]Patent: CN105399748,2016,A .

14
[ 18992-65-9 ]
C₃₂H₃₉B₂NO₄ [ No CAS ]

References: [1]Patent: CN105399748,2016,A .

15
[ 18992-65-9 ]
C₃₂H₂₃N₃O₄ [ No CAS ]

References: [1]Patent: CN105399748,2016,A .

16
[ 18992-65-9 ]
C₄₇H₃₃N₅ [ No CAS ]