[ CAS No. 65679-71-2 ] {[proInfo.proName]}

Name: 65679-71-2|3,6-Dichloro-9-(oxiran-2-ylmethyl)-9H-carbazole|95%
Brand: Ambeed
SKU: A471253
Rating: 91 (26 reviews)

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Quality Control of [ 65679-71-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 65679-71-2 ]

Product Details of [ 65679-71-2 ]

CAS No. :	65679-71-2	MDL No. :	MFCD00218276
Formula :	C₁₅H₁₁Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WQKPSQDZHVQBOF-UHFFFAOYSA-N
M.W :	292.16	Pubchem ID :	2775472
Synonyms :

Safety of [ 65679-71-2 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3077
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 65679-71-2 ]

* 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 [ 65679-71-2 ]

[ 65679-71-2 ] Synthesis Path-Downstream 1~7

1
[ 5599-71-3 ]
[ 3132-64-7 ]
[ 65679-71-2 ]

Yield	Reaction Conditions	Operation in experiment
23%	Stage #1: 3,6-dichloro-9H-carbazole With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,2-Epoxy-3-bromopropane In N,N-dimethyl-formamide at 20℃;
	Stage #1: 3,6-dichloro-9H-carbazole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1,2-Epoxy-3-bromopropane In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;

Reference： [1]MacMillan, Karen S.; Naidoo, Jacinth; Liang, Jue; Melito, Lisa; Williams, Noelle S.; Morlock, Lorraine; Huntington, Paula J.; Estill, Sandi Jo; Longgood, Jamie; Becker, Ginger L.; McKnight, Steven L.; Pieper, Andrew A.; De Brabander, Jef K.; Ready, Joseph M. [Journal of the American Chemical Society, 2011, vol. 133, # 5, p. 1428 - 1437]
[2]Cheng, Chia-Yi; Chang, Chun-Ping; Lauderdale, Tsai-Ling Yang; Yu, Guann-Yi; Lee, Jinq-Chyi; Jhang, Yi-Wun; Wu, Chien-Huang; Ke, Yi-Yu; Sadani, Amit A.; Yeh, Ching-Fang; Huang, I-Wen; Kuo, Yi-Ping; Tsai, De-Jiun; Yeh, Teng-Kuang; Tseng, Chen-Tso; Song, Jen-Shin; Liu, Yu-Wei; Tsou, Lun K.; Shia, Kak-Shan [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1191 - 1196]

2
[ 13754-41-1 ]
[ 65679-71-2 ]
4-benzyl-1-[3-(3,6-dichloro-carbazol-9-yl)-2-hydroxy-propyl]piperazin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: 4-benzyl-piperazin-2-one With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 3,6-dichloro-9-(oxiran-2-ylmethyl)-9H-carbazole In tetrahydrofuran; mineral oil at 120℃; for 0.5h; Microwave irradiation;

Reference： [1]Molette, Jeroime; Routier, Julie; Abla, Nada; Besson, Dominique; Bombrun, Agnes; Brun, Reto; Burt, Howard; Georgi, Katrin; Kaiser, Marcel; Nwaka, Solomon; Muzerelle, Mathilde; Scheer, Alexander [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1037 - 1041]

3
[ 5599-71-3 ]
[ 106-89-8 ]
[ 65679-71-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 3,6-dichloro-9H-carbazole With potassium hydroxide In N,N-dimethyl-formamide Cooling with ice; Stage #2: epichlorohydrin In N,N-dimethyl-formamide Cooling with ice;	1 Example 1, 3,6-dichloro-9-(epoxypropyl)-9H-carbazole (IIa): 3,6-dichlorocarbazole (470 mg, 2 mmol) was dissolved in 20 mL of DMF,Potassium hydroxide (135 mg, 2.4 mmol) was slowly added under ice-cooling,Add after mixing 0.5-1 hours,Until the potassium hydroxide solids are completely dissolved. Then, epichlorohydrin (2.4 mmol) was slowly added dropwise to the system,Reaction 4-5 hours.After completion of the reaction, 30 ml of water was added, and the mixture was extracted with ethyl acetate (30 ml x 3) and saturated sodium chloride solution (30 ml x 3). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was decompressed to recover the solvent. Purification by column chromatography gave 293 mg of white solid in 50% yield.
	Stage #1: 3,6-dichloro-9H-carbazole With potassium hydroxide In N,N-dimethyl-formamide at 0 - 4℃; for 0.5h; Stage #2: epichlorohydrin In N,N-dimethyl-formamide at 0℃;	9.1 Synthetic Step 1: N-alkylation In a dry round bottom flask, 3,6-dichlorocarbazole (705 mg, 3.0 mmol) was added to a solution of KOH (1.2 equiv., 3.6 mmol) in DMF (20 mL) at 0° C. After stirring the mixture for 30 min at 4° C., (+/-)-epichlorohydrin (2.5 equiv., 7.2 mmol) was added to the cooled flask drop wise. The reaction was stirred at 0° C. overnight. The reaction was removed from the ice bath and allowed to warm to room temperature. H2O (20 mL) was added to the mixture and white solid precipitant formed. The heterogeneous mixture was filtered and washed with H2O three times to provide a solid consisting of a mixture of N-alkylated product and remaining starting material. After applying high vacuum overnight, the white solid was used directly in any epoxide opening reaction.
	With potassium hydroxide In N,N-dimethyl-formamide at 4℃; Inert atmosphere;

	With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;
	With potassium hydroxide In N,N-dimethyl-formamide at 0℃;
	With potassium hydroxide In N,N-dimethyl-formamide at 0℃;

Reference： [1]Current Patent Assignee: NAT INST OF PARASITIC DISEASES CHINESE CENTER FOR; FIRST TEACHING HOSPITAL XINJIANG MEDICAL UNIV - CN106518750, 2017, A Location in patent: Paragraph 0182; 0183; 0184
[2]Current Patent Assignee: WARF (in: University of Wisconsin); UNIVERSITY OF WISCONSIN SYSTEM - US2013/331424, 2013, A1 Location in patent: Paragraph 0139
[3]Hurley, Katherine A.; Heinrich, Victoria A.; Hershfield, Jeremy R.; Demons, Samandra T.; Weibel, Douglas B. [ACS Medicinal Chemistry Letters, 2015, vol. 6, # 4, p. 466 - 471]
[4]Wang, Guangcheng; Wang, Jing; He, Dianxiong; Li, Xin; Li, Juan; Peng, Zhiyun [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2806 - 2809]
[5]Wang, Weisi; Sun, Xiao; Sun, Deheng; Li, Shizhu; Yu, Yang; Yang, Tingyuan; Yao, Junmin; Chen, Zhuo; Duan, Liping [ChemMedChem, 2016, vol. 11, # 24, p. 2675 - 2681]
[6]Wang, Weisi; Li, Qiang; Wei, Yufen; Xue, Jian; Sun, Xiao; Yu, Yang; Chen, Zhuo; Li, Shizhu; Duan, Liping [International Journal for Parasitology: Drugs and Drug Resistance, 2017, vol. 7, # 2, p. 191 - 199]

4
[ 65679-71-2 ]
[ 115-70-8 ]
2-[3-(3,6-dichloro-9H-carbazol-9-yl)-2-hydroxypropyl]amino}-2-ethylpropane-1,3-diol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 466 - 471

5
[ 5094-12-2 ]
[ 65679-71-2 ]
C₂₇H₂₅Cl₂N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 2h;	1-(9H-Carbazol-9-yl)-3-(2-methyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propan-2-one (4a) General procedure: A solution of 9-oxiranylmethylcarbazol 6a-c (1 mmol), γ-carboline 7a-f (1 mmol) and KOH (1 mmol) in DMF (20 mL) was stirred for 2 h at 50 °C and poured into H2O (100 mL). The precipitate formed was collected by filtration and chromatographed on silica gel (60 mesh) using hexane-ethyl acetate (2 : 1) as the eluent.

Reference： [1]Sokolov; Aksinenko, A. Yu.; Goreva; Epishina; Grigor'ev; Gabrel'yan; Vinogradova; Dubova; Shevtsov; Shevtsova; Bachurin [Russian Chemical Bulletin, 2016, vol. 65, # 5, p. 1346 - 1353][Izv. Akad. Nauk, Ser. Khim., 2016, # 5, p. 1346 - 1353,8]

6
[ 65679-71-2 ]
[ 5599-71-3 ]
[ 77233-11-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 2h;	1,3-Bis(9H-carbazol-9-yl)propan-2-ol (3a), 1-(9H-carbazol-9-yl)-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol (3b), 1-(9H-carbazol-9-yl)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3c), 1,3-bis(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol (3d)1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3e), 1,3-bis(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3f), 1-(9H-carbazol-9-yl)-(3,4-dihydro-1-carbazol-9-yl)propan-2-ol (4a) (general procedure). General procedure: The solution of 9-oxyranilmethylcarbazoles 5a-c (1 mmol), carbazoles 6a-c or tetrahydrocarbazoles 7a-f (1 mmol), and (1 mmol) in 20 mL of DMF was stirred for 2 h at 50 °C, then poured into 100 ml of H2O. The precipitate formed was collected by filtration, and purified by column chromatography using silica gel (60 mesh) and hexane-ethyl acetate (2 : 1) as eluent.

Reference： [1]Sokolov; Aksinenko, A. Yu.; Goreva; Epishina; Dubova; Dubrovskaya; Klochkov; Shevtsov; Shevtsova; Bachurin [Russian Chemical Bulletin, 2016, vol. 65, # 9, p. 2306 - 2311][Izv. Akad. Nauk, Ser. Khim., 2016, # 9, p. 2306 - 2311]

7
[ 942-01-8 ]
[ 65679-71-2 ]
1-(3,6-dichloro-9H-carbazol-9-yl)-3-(3,4-dihydro-1H-carbazol-9(2H)-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 2h;	1,3-Bis(9H-carbazol-9-yl)propan-2-ol (3a), 1-(9H-carbazol-9-yl)-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol (3b), 1-(9H-carbazol-9-yl)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3c), 1,3-bis(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol (3d)1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3e), 1,3-bis(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (3f), 1-(9H-carbazol-9-yl)-(3,4-dihydro-1-carbazol-9-yl)propan-2-ol (4a) (general procedure). General procedure: The solution of 9-oxyranilmethylcarbazoles 5a-c (1 mmol), carbazoles 6a-c or tetrahydrocarbazoles 7a-f (1 mmol), and (1 mmol) in 20 mL of DMF was stirred for 2 h at 50 °C, then poured into 100 ml of H2O. The precipitate formed was collected by filtration, and purified by column chromatography using silica gel (60 mesh) and hexane-ethyl acetate (2 : 1) as eluent.

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[ CAS No. 65679-71-2 ] {[proInfo.proName]}

Quality Control of [ 65679-71-2 ]

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Product Details of [ 65679-71-2 ]

Safety of [ 65679-71-2 ]

Application In Synthesis of [ 65679-71-2 ]

[ 65679-71-2 ] Synthesis Path-Downstream 1~7

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