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[ CAS No. 591-50-4 ]

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Chemical Structure| 591-50-4
Chemical Structure| 591-50-4
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CAS No. :591-50-4MDL No. :MFCD00001029
Formula : C6H5I Boiling Point : 188°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :204.01Pubchem ID :11575
Synonyms :

Computed Properties of [ 591-50-4 ]

TPSA : 0 H-Bond Acceptor Count : 0
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 591-50-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 591-50-4 ]

  • Upstream synthesis route of [ 591-50-4 ]
  • Downstream synthetic route of [ 591-50-4 ]

[ 591-50-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 591-50-4 ]
  • [ 101-23-5 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 17, p. 9414 - 9423
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  • [ 591-50-4 ]
  • [ 10401-11-3 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1991, # 22, p. 1630 - 1632
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  • [ 591-50-4 ]
  • [ 79991-24-5 ]
  • [ 105946-82-5 ]
  • [ 130201-21-7 ]
Reference: [1] Canadian Journal of Chemistry, 1982, vol. 60, p. 990 - 999
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  • [ 591-50-4 ]
  • [ 103962-05-6 ]
  • [ 175278-00-9 ]
  • [ 198206-33-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6
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  • [ 591-50-4 ]
  • [ 60511-85-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 3 h; Inert atmosphere; Reflux According to the preparation method of compound 66 in Example 3,the difference is,The synthetic route used is the above route,Using compound 113 'instead of carbazole,Using iodobenzene instead of compounds 1-5,To give compound 113-1 (yield 65percent)
Compound 1-5 (0.1623 mol) was added to toluene (450 mL)And then carbazole (0.1623 mol) was added under nitrogen protection,Sodium tert-butoxide (0.3246 mol), Pd2 (dba) 3 (0.0016 mol)And tri-tert-butylphosphine (0.0016 mol)And heated to reflux for 3 h,The silica gel funnel was filtered and the resulting filtrate was evaporated to dryness. The resulting solid was recrystallized from toluene to give compound 66 (yield 48percent):
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere to a 2-neck round bottom flask under nitrogen a mixture of B-1 2.1g (0.0082mol), iodo- benzene (Iodobenzene) 2.5g(0.013mol), Cu 0.312g (0.0049), 18- crown-6-ether (18-crown- 6-ether) 0.433g (0.0016mol), K2CO3 3.397g (0.0246mol) and o-DCB 20ml was stirred under reflux for 12 hours.The solution cooled to room temperature was extracted and concentrated by MC / H2O and separated with column chromatography (SiO2, Hexane:ethyl acetate = 10: 1) to obtain the title compound 2-B (1.76g, 64percent) as a white solid.
64% With 18-crown-6 ether; copper In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere Under nitrogen Two neck round bottom flask (rbf two neck: two neck round bottom flask) to the C-1 (2.1g, 0.0082mol), iodo- benzene (Iodobenzene) (2.5g, 0.013mol), Cu (0.312g , .0049), 18-crown-6-ether (18-Crown-6-ether) (0.433g, 0.0016mol), potassium carbonate (3.397g, 0.0246mol), ortho-dichlorobenzene in the mixture (20ml), It was stirred under reflux for 12 hour. Concentrated by extracting the solution cooled to room temperature with methylene chloride / H2O and purified by column chromatography (SiO2, hexane: ethyl acetate = 10: 1) to obtain a white solid compound C-2 by (1.76g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneInert atmosphere; Reflux Under nitrogen tunek round bottom flask (two neck round bottom flask) to A-1 (2.1g, 0.0082mol), Iodobenzene 2.5g (0.013mol), Cu 0.312g (0.0049 mol), 18-crown-6-ether 0.433g (0.0016mol), 20 ml of o-dichlorobenzene,K2CO3 (3.397g, 0.0246mol) was stirred under reflux for 16 hours . The solution was cooled to room temperature, MC (methylene chloride) / H2O and extracted with concentrated and separated by column chromatography (SiO2, hexane,ethyl acetate) 1/10) to give a white solid compound A-2 (1.76g , 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneReflux The compounds in the original neck rbf a nitrogen filled 250-2 (2.1g, 1.0eq), iodo-benzene (2.5g, 1.5eq), Cu (0.312g, 0.6eq), 18- crown-6-ether (0.433g , 0.2eq), a mixture of K2CO3 (3.397g, 3.0eq), 1,2- dichlorobenzene (20) was stirred for 16 hours at reflux temperature. The solution was concentrated and cooled to room temperature and extracted with MC / H2O and purified by column chromatography (SiO2, hexane: 1: ethyl acetate = 10) to obtain a white solid compound 250-3 separated by (1.76g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 16 h; Reflux A mixture of compound 73-2 (2.1 g, 1.0 equiv.),Iodobenzene (2.5 g, 1.5 eq.),Cu (0.312 g, 0.6 equiv),18-Crown-6-ether (0.433 g, 0.2 equiv),K2CO3 (3.397 g, 3.0 eq)And 1,2-dichlorobenzene (20 ml) was stirred at reflux temperature for 16 hours.The solution cooled to room temperature was extracted with MC / H2O and concentrated,And then purified by column chromatography (SiO2, hexane: ethyl acetate = 10: 1)Compound 73-3 (1.76 g, 64percent) was isolated as a white solid.
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 16 h; Inert atmosphere; Reflux A mixture of Compound B-1 (2.1 g, 0.0082 mol), iodobenzene (2.5 g, 0.013 mol), Cu (0.312 g, 0.0049), 18-crown-6-ether (0.433 g, 0.0016 mol), K2CO3(3.397 g, 0.0246 mol), and o-dichlorobenzene (o-DCB) (20 ml) was refluxed and stirred in a two neck round bottom flask (two neck r.b.f) under nitrogen for 16 hours. The mixed solution cooled to room temperature was extracted with MC (methylene chloride)/H2O and concentrated and separated by column chromatography (SiO2, hexane:ethyl acetate=10:1). As a result, a white solid compound B-2 was obtained (1.76 g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneInert atmosphere; Reflux Under nitrogen, compound B-1 (2.1 g, 0.0082 mol), Iodobenzene (2.5 g, 0.013 mol), Cu (0.312 g, 0.0049), 18-crown-6-ether (0.433 g, 0.0016 mol), and K2CO3 (3.397g, 0.0246 mol) in o-dichlorobenzene (o-DCB) (20 ml) was stirred at reflux condition for 16 hours. The solution cooled to room temperature was extracted with dichloromethane/H2O, concentrated and subjected to column chromatography (SiO2, hexane:ethyl acetate=10:1) to obtain white solid compound B-2 was obtained (1.76 g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere To a 2 neck round bottom flask under nitrogen was added the compound B-1 (2.1 g, 0.0082 mol), iodobenzene (Iodobenzene, 2.5 g,0.013 mol), Cu (0.312 g, 0.0049 mol), 18-crown-6-ether (0.433 g, 0.0016 mol)A mixture of o-DCB (20 ml) of K2CO3 (3.397 g, 0.0246 mol) was refluxed for 12 hours. The solution cooled to room temperature was washed with MC / H2O, And concentrated by column chromatography (SiO2, hexane: Ethyl acetate = 10: 1) to obtain white solidWater B-2 was obtained (1.76 g, 64percent).
64% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3 h; Reflux; Inert atmosphere The intermediate of indolocarbazole, benzene iodide (1.1 equivalent), bisdibenzylidene acetone palladium (0) (0.03 equivalent), tri-t-butylphosphine (1 equivalent), and sodium t-butoxide (2 equivalent) was added to toluene under an nitrogen environment, and the mixture was heated and refluxed for 3 hours. When a reaction was complete, the reaction solution was once filtered at a high temperature, twice extracted with brine, and an organic layer extracted therefrom was dried and concentrated. The concentrated solution was added to methanol in a dropwise fashion to obtain a solid, and a residue obtained after filtering the solid was separated and purified through column chromatography to obtain Intermediate of phenyl-indolocarbazole (64percent).
41% at 190℃; for 72 h; Inert atmosphere Example 1; Synthesis of Compound 1-19; Under a nitrogen atmosphere, 26.0 g (0.10 mol) of IC-1, 122.7 g (0.60 mol) of iodobenzene, 54.7g (0.29 mol) of copper iodide, 66.7 g (0.48 mol) of potassium carbonate, and 800 ml of quinoline were stirred for 72 hours while being heated at 190°C. The reaction solution wascooled toroomtemperature. Afterthat, distilledwater (500 ml) and dichloromethane (500 ml) were then added while being stirred. The precipitated crystal was separated by filtration. The organic layer was then washed with distilled water (3.x.500 ml). The organic layer was dried over anhydrous magnesium sulfate. The magnesium sulfate was then separated by filtration and the solvent was subjected to vacuum distillation. The resultant residue was purified by silica gel column chromatography to afford 13.7 g (41percent yield) of an intermediate B as a white solid.
40.6% at 190℃; for 72 h; In a 1000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 mmol) of the white powder obtained above, 122.7 g (601.4 mmol) of iodobenzene, 54.7 g (287.2 mmol) of copper iodide, 66.7g (482.6 mmol) of potassium carbonate, and 800 ml of quinoline and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmol, 40.6percent yield) of a white powder.; Then, 26.0 g (101.4 mmol) of the white powder obtained above, 122.7 g (601.4 mmol) of iodobenzene, 54.7 g (287.2 mmol) of copper iodide, 66.7 g (482.6 mmol) of potassium carbonate, and 800 ml of quinoline were placed in a 1000-ml three-necked flask that had been deaerated and filled with nitrogen and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmol, 40.6percent yield) of a white powder.; Then, 26.0 g (0.101 mole) of the white powder obtained above, 122.7 g (0.601 mole) of iodobenzene, 54.7 g (0.287 mole) of copper iodide, 66.7 g (0.482 mole) of potassium carbonate, and 800 ml of quinoline were placed in a 1000-ml three-necked flask that had been deaerated and filled with nitrogen and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (0.04 mole, 40.8percent yield) of a white powder.
40.6% With potassium carbonate In quinoline at 190℃; for 72 h; In a 1000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 mmoles) of the white powder obtained above, 122.7 g (601.4 mmoles) of iodobenzene, 54.7 g (287.2 mmoles) of copper iodide, and 66.7 g (482.6 mmoles) of potassium carbonate, then 800 ml of quinoline was added, and the mixture was stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 500 ml of water and dried over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmoles, 40.6percent yield) of white solid A or 11-phenylindolo[2,3-a]carbazole.
40.8% at 190℃; for 72 h; Inert atmosphere Next, in a 1,000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (0.101 mole) of the white powder A obtained above, 122.7 g (0.601 mole) of iodobenzene, 54.7 g (0.287 mole) of copper iodide, 66.7 g (0.482 mole) of potassium carbonate, and 800 ml of quinoline and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were collected by filtration. The filtrate was transferred to a 2,000-ml separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 500 ml of water and then dehydrated over magnesium sulfate, the magnesium sulfate was filtered out, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (0.04 mole, 40.8percent yield) of a white powder B.
40.6% at 190℃; for 72 h; Inert atmosphere Next, 26.0 g (0.10 mol) of the white powder obtained in the foregoing, 122.7 g (0.60 mol) of iodobenzene, 54.7 g (0.29 mol) of copper iodide, 66.7 g (0.48 mol) of potassium carbonate, and 800 ml of quinoline were loaded into a 1,000-ml three-necked flask purged with nitrogen and stirred. After that, the mixture was heated to 190° C. and stirred for 72 hr. Once the mixture was cooled to room temperature, and then 500 ml of water and 500 ml of dichloromethane were added to the mixture, followed by stirring. After that, the resultant yellow crystal was taken by filtration. The filtrate was transferred to a 2,000-ml separating funnel, and was fractionated into an organic layer and an aqueous layer. The organic layer was washed with 500 ml of water three times, and then the resultant organic layer was dried with magnesium sulfate. Once magnesium sulfate was separated by filtration and then the solvent was distilled off under reduced pressure. After that, the residue was purified by column chromatography to provide 13.7 g (0.041 mol, yield: 40.6percent) of Intermediate A as a white solid.

Reference: [1] Patent: CN106928237, 2017, A, . Location in patent: Paragraph 0152; 0153; 0154; 0155; 0166-0168
[2] Patent: KR2016/8819, 2016, A, . Location in patent: Paragraph 0189; 0191; 0195; 0196
[3] Patent: KR2015/132019, 2015, A, . Location in patent: Paragraph 0227; 0228; 0231; 0232
[4] Patent: KR2016/1702, 2016, A, . Location in patent: Paragraph 0192-0193; 0196-0197
[5] Patent: KR101551895, 2015, B1, . Location in patent: Paragraph 0307; 0312; 0313
[6] Patent: CN105408333, 2016, A, . Location in patent: Paragraph 0252; 0257; 0258
[7] Patent: KR101558495, 2015, B1, . Location in patent: Paragraph 0342; 0343; 0346; 0347
[8] Patent: KR2016/41019, 2016, A, . Location in patent: Paragraph 0167; 0168; 0172; 0173
[9] Patent: KR2017/2208, 2017, A, . Location in patent: Paragraph 0258-0259; 0263-0264
[10] Patent: US2018/47916, 2018, A1, . Location in patent: Paragraph 0137
[11] Patent: EP2415772, 2012, A1, . Location in patent: Page/Page column 35
[12] Patent: EP1956022, 2008, A1, . Location in patent: Page/Page column 33-34; 36
[13] Patent: EP2080762, 2009, A1, . Location in patent: Page/Page column 24
[14] Patent: EP2166011, 2010, A1, . Location in patent: Page/Page column 20
[15] Patent: US9985219, 2018, B2, . Location in patent: Page/Page column 304; 306
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  • [ 591-50-4 ]
  • [ 222-19-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
51% With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 24 h; Inert atmosphere; Reflux In an argon atmosphere, 90 ml of dehydrated 1,4-dioxane was added to a mixture of 15.0 g (58.5 mmol) of indolo[2,3-a]carbazole (synthesized according to the method of Synlett p.42-48 (2005)), 11.9 g (58.5 mmol) of iodobenzene, 11.2 g (58.5 mmol) of copper iodide, 20.0 g (175.5 mmol) of trans-1,2-cyclohexanediamine, and 37.3 g (175.5 mmol) of tripotassium phosphate, and the resultant mixture was stirred for 24 h while refluxing under heating. The reaction solution was concentrated under reduced pressure. The obtained residue was added with 500 ml of toluene, heated to 120 °C, and then filtered to remove insolubles. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography, to obtain 10.0 g of white solid, which was identified as the following intermediate 2-1 by FD-MS analysis (yield: 51percent).
Reference: [1] Patent: EP2738166, 2014, A1, . Location in patent: Paragraph 0167
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  • [ 591-50-4 ]
  • [ 1984-49-2 ]
  • [ 1060735-14-9 ]
YieldReaction ConditionsOperation in experiment
5.59 g With copper; potassium carbonate In nitrobenzene at 180℃; for 4 h; Inert atmosphere Then under a nitrogen stream, the 14.0g of 9H, 9'H-3,3'- Dicarbazole,Iodine benzene 8.59 g, nitrobenzene 400ml, 5.72 g of copper powder with 12.44 g of potassium carbonate mixturesolution heated to 180 ° C for 4 hours. After coolingto room temperature, the nitrobenzene was removed by distillation under reducedpressure, followed by purification by silica gel chromatography, vacuum dryingto obtain 5.59g of 9-phenyl-9H, 9H-3,3-dicarbazole.
Reference: [1] Patent: TWI523840, 2016, B, . Location in patent: Page/Page column 52
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  • [ 591-50-4 ]
  • [ 1060735-14-9 ]
Reference: [1] Patent: KR2015/133998, 2015, A,
[2] Patent: KR2017/58874, 2017, A,
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  • [ 98-80-6 ]
  • [ 591-50-4 ]
  • [ 1008106-86-2 ]
Reference: [1] Catalysis Communications, 2013, vol. 32, p. 15 - 17
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  • [ 591-50-4 ]
  • [ 1001911-63-2 ]
Reference: [1] Patent: KR2015/61811, 2015, A,
[2] Patent: KR101649950, 2016, B1,
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