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502161-03-7

Basic Information
CAS No.: 502161-03-7
Name: 9H-Carbazole,3-iodo-9-phenyl-
Molecular Structure:
Molecular Structure of 502161-03-7 (9H-Carbazole,3-iodo-9-phenyl-)
Formula: C18H12IN
Molecular Weight: 369.20
Synonyms: 3-Iodo-N-phenylcarbazole;N-Phenyl-3-iodocarbazole;
EINECS: 808-151-1
Density: 1.56 g/cm3
Melting Point: 103.0 to 107.0 °C
Boiling Point: 480.6 °C at 760 mmHg
Flash Point: 244.5 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 4.93000
LogP: 5.38830
Synthetic route
1150-62-5

N-phenylcarbazole

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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%
108-86-1

bromobenzene

16807-13-9

3-iodocarbazole

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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%
1150-62-5

N-phenylcarbazole

A

57103-21-6

3,6-diiodo-9-phenyl-9H-carbazole

B

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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;
86-74-8

9H-carbazole

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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
108-86-1

bromobenzene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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
591-50-4

iodobenzene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
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
16807-13-9

3-iodocarbazole

591-50-4

iodobenzene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;
1066-54-2

trimethylsilylacetylene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C23H21NSi

Conditions
ConditionsYield
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]

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluorobutyl)-9-phenyl-9H-carbazole

Conditions
ConditionsYield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;96%
62-53-3

aniline

502161-03-7

3-iodo-9-phenyl-9H-carbazole

894791-43-6

(N-phenyl)-N-(9-phenyl-9H-carbazole-3-yl)amine

Conditions
ConditionsYield
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%
116-14-3

polytetrafluoroethylene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluoroethyl)-9-phenyl-9H-carbazole

Conditions
ConditionsYield
With C12H8CuFN2; cesium fluoride In N,N-dimethyl-formamide at 80℃; for 72h; Inert atmosphere;92%
60007-39-8

pentafluoroethylcopper(I)

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluoroethyl)-9-phenyl-9H-carbazole

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

[(1,10-phenanthroline)2Cu][n-C3F7CO2]·benzene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluoropropyl)-9-phenyl-9H-carbazole

Conditions
ConditionsYield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;91%
3262-89-3

triphenylboroxine

502161-03-7

3-iodo-9-phenyl-9H-carbazole

1028648-09-0

3,9-diphenyl-9H-carbazole

Conditions
ConditionsYield
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%
667-27-6

Ethyl bromodifluoroacetate

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C22H17F2NO2

Conditions
ConditionsYield
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%
1592-95-6

3-bromo-9H-carbazole

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3'-bromo-9-phenyl-9H-3,9'-bicarbazole

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;89%
390-16-9

4-fluoro-9H-carbazole

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C30H19FN2

Conditions
ConditionsYield
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]

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluoropentyl)-9-phenyl-9H-carbazole

Conditions
ConditionsYield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;86%
201230-82-2

carbon monoxide

C55H46CuF3P3

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C20H12F3NO

Conditions
ConditionsYield
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

502161-03-7

3-iodo-9-phenyl-9H-carbazole

9-phenyl-3-(tetrahydro-2H-pyran-4-yl)-9H-carbazole

Conditions
ConditionsYield
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%
106-40-1

4-bromo-aniline

502161-03-7

3-iodo-9-phenyl-9H-carbazole

N-(4-bromophenyl)-9-phenyl-N-(9-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-amine

Conditions
ConditionsYield
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

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C54H46N4O

Conditions
ConditionsYield
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]

502161-03-7

3-iodo-9-phenyl-9H-carbazole

3-(perfluoroethyl)-9-phenyl-9H-carbazole

Conditions
ConditionsYield
In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;83%
637-69-4

4-Methoxystyrene

7031-93-8

2,2,6,6-tetramethylpiperidin-1-ol

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C36H40N2O2

Conditions
ConditionsYield
With 2,6-di(t-butyl)-4-phenylphenol; caesium carbonate In dimethyl sulfoxide at 20℃; for 16h; Irradiation; Inert atmosphere;83%
108714-73-4

9,9-dimethyl-9H-fluoren-2-ylamine

502161-03-7

3-iodo-9-phenyl-9H-carbazole

1268835-64-8

C33H26N2

Conditions
ConditionsYield
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

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C36H24N2

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

C27H21NO2

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C45H32N2O2

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

C27H21NO

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C45H32N2O

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 100℃; for 20h;81%
692-51-3, 55364-29-9, 55364-28-8

(E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane

502161-03-7

3-iodo-9-phenyl-9H-carbazole

1373497-83-6

(E)-9-phenyl-3-(3,3,3-trifluoroprop-1-enyl)-9H-carbazole

Conditions
ConditionsYield
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%
502161-03-7

3-iodo-9-phenyl-9H-carbazole

(N-heterocyclic carbene)Ag(SCF2H)

(N-heterocyclic carbene)Ag(SCF2H)

C19H13F2NS

Conditions
ConditionsYield
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

502161-03-7

3-iodo-9-phenyl-9H-carbazole

methyl 2-(9-phenyl-9H-carbazol-3-yl)propanoate

Conditions
ConditionsYield
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%
134-32-7

1-amino-naphthalene

502161-03-7

3-iodo-9-phenyl-9H-carbazole

894791-44-7

N-(naphthalen-2yl)-9-phenyl-9H-carbazol-3-amine

Conditions
ConditionsYield
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%
73183-34-3

bis(pinacol)diborane

502161-03-7

3-iodo-9-phenyl-9H-carbazole

1126522-69-7

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole

Conditions
ConditionsYield
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%
113964-72-0

triphenyl(pyridin-4-yl)phosphonium trifluoromethanesulfonate

502161-03-7

3-iodo-9-phenyl-9H-carbazole

9-phenyl-3-(pyridin-4-yl)-9H-carbazole

Conditions
ConditionsYield
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

502161-03-7

3-iodo-9-phenyl-9H-carbazole

N1,N1-diisopropyl-N2-(3-(9-phenyl-9H-carbazol-3-yl)propyl)oxalamide

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

C27H21NO

502161-03-7

3-iodo-9-phenyl-9H-carbazole

C45H32N2O

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 100℃; for 20h;78%
Raw Materials
1150-62-5
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    3-Iodo-9-phenylcarbazole

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Specification

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