N-phenylcarbazole
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With iodine; acetic acid; periodic acid In water at 80℃; for 2h; | 87% |
With iodine; acetic acid; periodic acid In water at 80℃; for 2h; | 87% |
With iodine; acetic acid; periodic acid at 80℃; for 2h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
Stage #1: 3-iodocarbazole With sodium hydride In N,N-dimethyl-formamide at 80℃; for 1h; Stage #2: bromobenzene In N,N-dimethyl-formamide | 65.1% |
N-phenylcarbazole
A
3,6-diiodo-9-phenyl-9H-carbazole
B
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With potassium iodate; potassium iodide In acetic acid at 55℃; for 5h; | A 7.3 % Chromat. B 81.2 % Chromat. |
With potassium iodate; sulfuric acid; potassium iodide In ethanol at 55℃; for 5h; | A 99.2 % Chromat. B 0.8 % Chromat. |
With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 25℃; Product distribution; |
9H-carbazole
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2: iodine; sulfuric acid / water; methanol / 20 h View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2: iodine; sulfuric acid / methanol; water / 20 h / 5 °C / Cooling View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; copper dichloride / dimethyl sulfoxide / 24 h / 160 °C 2: acetic acid; iodine; periodic acid / 2 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium iodide; acetic acid / 110 °C 1.2: 0.17 h / 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: 18-crown-6 ether; potassium carbonate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide / 8 h / 170 °C 2: periodic acid; acetic acid; iodine / 2 h / 80 °C / Inert atmosphere View Scheme |
bromobenzene
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2: iodine; sulfuric acid / water; methanol / 20 h View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2: iodine; sulfuric acid / methanol; water / 20 h / 5 °C / Cooling View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; copper dichloride / dimethyl sulfoxide / 24 h / 160 °C 2: acetic acid; iodine; periodic acid / 2 h / 80 °C View Scheme |
iodobenzene
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 18-crown-6 ether; potassium carbonate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide / 8 h / 170 °C 2: periodic acid; acetic acid; iodine / 2 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 99% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 99% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere; | 99% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 5h; | 82% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 5h; | 82% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 96% |
aniline
3-iodo-9-phenyl-9H-carbazole
(N-phenyl)-N-(9-phenyl-9H-carbazole-3-yl)amine
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 1.5h; Reflux; | 94% |
With tris-(dibenzylideneacetone)dipalladium(0); PtBu3; potassium tert-butylate In toluene at 85℃; for 4h; | 79% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 3h; | 70% |
polytetrafluoroethylene
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With C12H8CuFN2; cesium fluoride In N,N-dimethyl-formamide at 80℃; for 72h; Inert atmosphere; | 92% |
pentafluoroethylcopper(I)
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 36h; Inert atmosphere; Sealed tube; Glovebox; | 92% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 91% |
triphenylboroxine
3-iodo-9-phenyl-9H-carbazole
3,9-diphenyl-9H-carbazole
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine With potassium tert-butylate; zinc(II) chloride In 1-methyl-pyrrolidin-2-one at 23℃; for 1h; Inert atmosphere; Glovebox; Stage #2: 3-iodo-9-phenyl-9H-carbazole In 1-methyl-pyrrolidin-2-one at 110℃; for 24h; Inert atmosphere; Glovebox; | 90% |
Conditions | Yield |
---|---|
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tetrabutylammomium bromide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc In tetrahydrofuran at 60℃; for 12h; Inert atmosphere; | 89% |
3-bromo-9H-carbazole
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 20h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane at 120℃; for 4h; Inert atmosphere; | 87% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 86% |
Conditions | Yield |
---|---|
With diiodobis(triphenylphosphino)palladium(II) In 5,5-dimethyl-1,3-cyclohexadiene at 70℃; under 15001.5 Torr; for 24h; Autoclave; | 86% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); pyridine-2-carboxamidine hydrochloride; 1-Bromo-2-chloroethane; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 30℃; Inert atmosphere; Flow reactor; | 86% |
4-bromo-aniline
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With copper(l) iodide; tetraethoxy orthosilicate; caesium carbonate at 145℃; for 38h; Inert atmosphere; | 85% |
With copper(l) iodide; tetraethoxy orthosilicate; caesium carbonate at 145℃; for 38h; | 30% |
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); N-(tert-butyloxycarbonyl)-L-isoleucine; silver carbonate In toluene at 100℃; for 15h; Sealed tube; stereoselective reaction; | 83% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 83% |
4-Methoxystyrene
2,2,6,6-tetramethylpiperidin-1-ol
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With 2,6-di(t-butyl)-4-phenylphenol; caesium carbonate In dimethyl sulfoxide at 20℃; for 16h; Irradiation; Inert atmosphere; | 83% |
9,9-dimethyl-9H-fluoren-2-ylamine
3-iodo-9-phenyl-9H-carbazole
C33H26N2
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 5h; | 82% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 6h; Inert atmosphere; | 62% |
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In 1,2-dichloro-benzene for 12h; Reflux; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 85℃; for 2h; | 81% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 100℃; for 20h; | 81% |
(E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane
3-iodo-9-phenyl-9H-carbazole
(E)-9-phenyl-3-(3,3,3-trifluoroprop-1-enyl)-9H-carbazole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tris(2,4,6-trimethylphenyl)phosphine; cesium fluoride In N,N-dimethyl-formamide at 80℃; for 2.5h; Hiyama cross-coupling reaction; Inert atmosphere; | 80% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With (xantphos)Pd(II) (3-py)(Br); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 50℃; for 6h; Reagent/catalyst; | 80% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With pyridine; nickel(II) iodide; 4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Schlenk technique; Inert atmosphere; | 80% |
1-amino-naphthalene
3-iodo-9-phenyl-9H-carbazole
N-(naphthalen-2yl)-9-phenyl-9H-carbazol-3-amine
Conditions | Yield |
---|---|
With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In hexane; xylene at 90℃; for 7h; | 79% |
With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In hexane; xylene at 90℃; for 7h; | 79% |
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In xylene at 90℃; for 7h; | 79% |
bis(pinacol)diborane
3-iodo-9-phenyl-9H-carbazole
9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium tert-butylate In toluene at 90℃; for 6h; Inert atmosphere; | 79% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 12h; Reflux; | 65% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; | 62% |
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; | 62% |
triphenyl(pyridin-4-yl)phosphonium trifluoromethanesulfonate
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With palladium diacetate; silver perchlorate; potassium carbonate; ruphos In acetone at 65℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 79% |
3-iodo-9-phenyl-9H-carbazole
Conditions | Yield |
---|---|
With palladium diacetate; silver carbonate In 1,3,5-trimethyl-benzene at 130℃; for 36h; Inert atmosphere; Sealed tube; | 78% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 100℃; for 20h; | 78% |
The 3-Iodo-9-phenylcarbazole, with the CAS registry number 502161-03-7, is also known as 9H-Carbazole, 3-iodo-9-phenyl-. It belongs to the product category of API Intermediates. This chemical's molecular formula is C18H12IN and molecular weight is 369.19905. Its systematic name is called 3-iodo-9-phenyl-9H-carbazole.
Physical properties of 3-Iodo-9-phenylcarbazole: (1)ACD/LogP: 7.23; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#Freely Rotating Bonds: 1; (5)Index of Refraction: 1.704; (6)Molar Refractivity: 91.91 cm3; (7)Molar Volume: 236.7 cm3; (8)Surface Tension: 49.2 dyne/cm; (9)Density: 1.55 g/cm3; (10)Flash Point: 244.5 °C; (11)Enthalpy of Vaporization: 74.51 kJ/mol; (12)Boiling Point: 480.6 °C at 760 mmHg; (13)Vapour Pressure: 2.14E-09 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: Ic3cc2c1ccccc1n(c2cc3)c4ccccc4
(2)InChI: InChI=1/C18H12IN/c19-13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12H
(3)InChIKey: PJUAIXDOXUXBDR-UHFFFAOYAU
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