502161-03-7

Basic information

• Product Name: 3-Iodo-N-phenylcarbazole
• Synonyms: 3-Iodo-N-phenylcarbazole;3-Iodo-9-phenylcarbazole;3-iodo-9-phenyl-9H-carbazole;3-iodo-N-phenylcarbazol;3-Iodo-N-phenylcarba;3-iodo-9-phenylcarbazole,3-Iodo-9-phenylcarbazole;3-Iodo-9-phenylcarbazole/ 3-Iodo-N-phenylcarbazole;3-Iodo-N-Phenylcarbazole (IPC)
• CAS NO: 502161-03-7
• Molecular Formula: C₁₈H₁₂IN
• Molecular Weight: 369.19905
• EINECS: 1533716-785-6
• Product Categories: API intermediates;OLED materials,pharm chemical,electronic
• Mol File: 502161-03-7.mol
• Article Data: 28

Chemical Properties

• Melting Point: 103.0 to 107.0 °C
• Boiling Point: 480.6 °C at 760 mmHg
• Flash Point: 244.5 °C
• Appearance: /
• Density: 1.56 g/cm³
• Vapor Pressure: 2.14E-09mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Iodo-N-phenylcarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-N-phenylcarbazole(502161-03-7)
• EPA Substance Registry System: 3-Iodo-N-phenylcarbazole(502161-03-7)

Safety Data

• Hazardous Substances Data: 502161-03-7(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

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

Synthetic route

N-phenylcarbazole (1150-62-5) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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%

bromobenzene (108-86-1) + 3-iodocarbazole (16807-13-9) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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 (1150-62-5) → 3,6-diiodo-9-phenyl-9H-carbazole (57103-21-6) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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 (86-74-8) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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 (108-86-1) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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 (591-50-4) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

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

3-iodocarbazole (16807-13-9) + iodobenzene (591-50-4) → 3-iodo-9-phenyl-9H-carbazole (502161-03-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;

trimethylsilylacetylene (1066-54-2) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C23H21NSi

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%

[(1,10-phenanthroline)2Cu][n-C4F9CO2] + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluorobutyl)-9-phenyl-9H-carbazole

Conditions	Yield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	96%

aniline (62-53-3) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → (N-phenyl)-N-(9-phenyl-9H-carbazole-3-yl)amine (894791-43-6)

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 (116-14-3) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluoroethyl)-9-phenyl-9H-carbazole

Conditions	Yield
With C12H8CuFN2; cesium fluoride In N,N-dimethyl-formamide at 80℃; for 72h; Inert atmosphere;	92%

pentafluoroethylcopper(I) (60007-39-8) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluoroethyl)-9-phenyl-9H-carbazole

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 36h; Inert atmosphere; Sealed tube; Glovebox;	92%

[(1,10-phenanthroline)2Cu][n-C3F7CO2]·benzene + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluoropropyl)-9-phenyl-9H-carbazole

Conditions	Yield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	91%

triphenylboroxine (3262-89-3) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3,9-diphenyl-9H-carbazole (1028648-09-0)

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%

Ethyl bromodifluoroacetate (667-27-6) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C22H17F2NO2

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 (1592-95-6) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3'-bromo-9-phenyl-9H-3,9'-bicarbazole

Conditions	Yield
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	89%

4-fluoro-9H-carbazole (390-16-9) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C30H19FN2

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane at 120℃; for 4h; Inert atmosphere;	87%

[(1,10-phenanthroline)2Cu][n-C5F11CO2] + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluoropentyl)-9-phenyl-9H-carbazole

Conditions	Yield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	86%

carbon monoxide (201230-82-2) + C55H46CuF3P3 + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C20H12F3NO

Conditions	Yield
With diiodobis(triphenylphosphino)palladium(II) In 5,5-dimethyl-1,3-cyclohexadiene at 70℃; under 15001.5 Torr; for 24h; Autoclave;	86%

1,3-dioxoisoindolin-2-yl tetrahydro-2H-pyran-4-carboxylate + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 9-phenyl-3-(tetrahydro-2H-pyran-4-yl)-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 (106-40-1) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N-(4-bromophenyl)-9-phenyl-N-(9-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-amine

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%

(R)-N-(pyridinyl-2-ylcarbonyl)rimantadine + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C54H46N4O

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%

[(1,10-phenanthroline)2Cu][O2CC2F5] + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(perfluoroethyl)-9-phenyl-9H-carbazole

Conditions	Yield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	83%

4-Methoxystyrene (637-69-4) + 2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C36H40N2O2

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 (108714-73-4) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C33H26N2 (1268835-64-8)

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%

C18H13N + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C36H24N2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In 1,2-dichloro-benzene for 12h; Reflux; Inert atmosphere;	82%

C27H21NO2 + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C45H32N2O2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 85℃; for 2h;	81%

C27H21NO + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C45H32N2O

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 (692-51-3, 55364-29-9, 55364-28-8) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → (E)-9-phenyl-3-(3,3,3-trifluoroprop-1-enyl)-9H-carbazole (1373497-83-6)

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 (502161-03-7) + (N-heterocyclic carbene)Ag(SCF2H) → C19H13F2NS

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%

Methyl 2-<(methoxallyl)oxy>acetate + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → methyl 2-(9-phenyl-9H-carbazol-3-yl)propanoate

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 (134-32-7) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N-(naphthalen-2yl)-9-phenyl-9H-carbazol-3-amine (894791-44-7)

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 (73183-34-3) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1126522-69-7)

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 (113964-72-0) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 9-phenyl-3-(pyridin-4-yl)-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%

N1,N1-diisopropyl-N2-propyloxalamide + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N1,N1-diisopropyl-N2-(3-(9-phenyl-9H-carbazol-3-yl)propyl)oxalamide

Conditions	Yield
With palladium diacetate; silver carbonate In 1,3,5-trimethyl-benzene at 130℃; for 36h; Inert atmosphere; Sealed tube;	78%

C27H21NO + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → C45H32N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 100℃; for 20h;	78%

Upstream product

• 16807-13-9 3-iodocarbazole 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 86-74-8 9H-carbazole 
• 1150-62-5 N-phenylcarbazole 

Downstream Products

• 1028647-93-9 3-(4-bromophenyl)-9-phenyl-9H-carbazole 
• 854952-58-2 N-phenyl-9H-carbazol-3-boronic acid 
• 1202685-66-2 C₄₂H₂₉N₃ 
• 1026033-51-1 9-phenyl-9H-3,9'-bicarbazole 
• 1026033-57-7 3-(3-chlorophenyl)-9-phenyl-9H-carbazole 
• 1026033-78-2 N,N,N'-tris(9-phenyl-3-carbazolyl)-N'-phenyl-1,4-diaminobenzene 
• 1372005-73-6 C₄₅H₃₄N₂ 
• 913190-42-8 3-ethynyl-9-phenyl-9H-carbazole 
• 1028648-09-0 3,9-diphenyl-9H-carbazole 

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