1024598-06-8

Basic information

• Product Name: 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole
• Synonyms: 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole;Indolo[2,3-a]carbazole, 11,12-dihydro-11-phenyl-;11-phenylindolo[2,3-a]carbazole;11-phenyl-11,12-dihydroindolo[2,3-a]carbazole;11,12-Dihydro-11-phenylindolo[2,3-a]carbazole
• CAS NO: 1024598-06-8
• Molecular Formula: C₂₄H₁₆N₂
• Molecular Weight: 332.39724
• Mol File: 1024598-06-8.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 598.8±32.0 °C(Predicted)
• Appearance: /
• Density: 1.26
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.78±0.30(Predicted)
• CAS DataBase Reference: 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole(1024598-06-8)
• EPA Substance Registry System: 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole(1024598-06-8)

Safety Data

• Hazardous Substances Data: 1024598-06-8(Hazardous Substances Data)

Usage

General Description

11,12-Dihydro-11-phenylindolo[2,3-a]carbazole, also known as dihydrophenylindole, is a chemical compound that belongs to the class of indole alkaloids. It is an important intermediate in the synthesis of bioactive molecules and is used in chemical research and pharmaceutical development. 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole is known for its potential anti-cancer properties and has been studied for its ability to inhibit the growth of tumor cells. It is a dark brown solid at room temperature and is soluble in common organic solvents. Its chemical structure contains a fused carbazole ring with a phenyl group, giving it unique properties and potential applications in various fields.

Synthetic route

bromobenzene (108-86-1) + 11,12-dihydroindolo[2,3-a]carbazole (60511-85-5) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 160℃; for 48h;	83%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 24h; Inert atmosphere; Reflux;	75%
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 17h; Inert atmosphere;	73%

9-phenyl-9H-carbazol-1-amine (855180-11-9) + (2-bromophenyl)boronic acid (244205-40-1) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Stage #1: 9-phenyl-9H-carbazol-1-amine With hydrogen bromide; dihydrogen peroxide In water; acetonitrile at -20℃; Stage #2: (2-bromophenyl)boronic acid With palladium diacetate; caesium carbonate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere; Reflux;	78.4%

2-(2-nitrophenyl)-9-phenyl-9H-carbazole (1361125-94-1) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 12h; Inert atmosphere;	71.5%
With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; Inert atmosphere;	55%

iodobenzene (591-50-4) + 11,12-dihydroindolo[2,3-a]carbazole (60511-85-5) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux;	65%
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 12h; Reflux; Inert atmosphere;	64%
With 18-crown-6 ether; copper In 1,2-dichloro-benzene for 12h; Reflux; Inert atmosphere;	64%

bromobenzene (108-86-1) + tri-tert-butyl phosphine (13716-12-6) + 11,12-dihydroindolo[2,3-a]carbazole (60511-85-5) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In water; toluene	55%

iodobenzene (591-50-4) + indolo[2,3-a]carbazole (222-19-5) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 24h; Inert atmosphere; Reflux;	51%

phenylhydrazine hydrochloride (59-88-1) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4.08 h / 20 - 65 °C / Inert atmosphere 1.2: 15 h / 100 °C 2.1: potassium carbonate; copper(l) iodide; quinoline / 72 h / 190 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4 h / 60 °C / Inert atmosphere 1.2: 12 h / 100 °C 2.1: copper; 18-crown-6 ether / 1,2-dichloro-benzene / 12 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4 h / 60 °C 1.2: 100 °C 2.1: copper; potassium carbonate; 18-crown-6 ether / 1,2-dichloro-benzene / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4 h / 60 °C / Inert atmosphere 1.2: 12 h / 100 °C 2.1: potassium carbonate; copper; 18-crown-6 ether / 1,2-dichloro-benzene / 12 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: ethanol / 0.5 h 1.2: 10 h / 65 °C 2.1: copper; 18-crown-6 ether; potassium carbonate / 1,2-dichloro-benzene / 48 h / 180 °C View Scheme

cyclohexane-1,2-dione (765-87-7) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4.08 h / 20 - 65 °C / Inert atmosphere 1.2: 15 h / 100 °C 2.1: potassium carbonate; copper(l) iodide; quinoline / 72 h / 190 °C / Inert atmosphere View Scheme

phenyl hydrazine hydrochloride → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / ethanol / 4 h / 60 °C / Inert atmosphere 1.2: 12 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; copper; 18-crown-6 ether / 1,2-dichloro-benzene / 12 h / Reflux; Inert atmosphere View Scheme

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water; ethanol / 24 h / 120 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 100 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 100 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere View Scheme

2-nitrophenyl bromide (577-19-5) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water; ethanol / 24 h / 120 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 100 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 100 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); calcium carbonate / 1,4-dioxane / 12 h / Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere 3: caesium carbonate; palladium diacetate; tri-tert-butyl phosphine / toluene / 20 °C / Inert atmosphere; Reflux View Scheme

2-(2-nitrophenyl)-9-phenyl-9H-carbazole (1361125-94-1) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 5-phenyl-5,11-dihydro-indolo[3,2-b]carbazole (1316311-27-9)

Conditions	Yield
With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; Inert atmosphere; Overall yield = 63 %;

benzene-1,4-diboronic acid bispinacol ester (99770-93-1) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); calcium carbonate / 1,4-dioxane / 12 h / Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere 3: caesium carbonate; palladium diacetate; tri-tert-butyl phosphine / toluene / 20 °C / Inert atmosphere; Reflux View Scheme

2,2''-dinitro-p-terphenyl (34673-74-0) → 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere 2: caesium carbonate; palladium diacetate; tri-tert-butyl phosphine / toluene / 20 °C / Inert atmosphere; Reflux View Scheme

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2,4‐bis({[1,1'‐biphenyl]‐4‐yl})‐6‐chloro‐1,3,5‐triazine → C51H33N5

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil for 6h; Inert atmosphere;	90%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;	81%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (30894-93-0) → C39H24ClN5

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene for 3h; Reflux;	88%

iodobenzene (591-50-4) + 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) → 11,12-diphenyl-11,12-dihydro-indolo[2,3-a]carbazole

Conditions	Yield
With 3,5-ditertbutyl salicylic acid; copper; potassium carbonate for 48h; Reflux; Inert atmosphere;	87%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-bromo-5-phenyl-1,3-oxazole (92629-11-3) → 2-phenyl-5-(12-phenylindolo[2,3-a]carbazole-11(12H)-yl)oxazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 160℃; for 48h;	86%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-bromobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole (1611489-35-0) → C37H22N4S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	85%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 1,4-bromoiodobenzene (589-87-7) → C30H19BrN2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3h; Reflux; Inert atmosphere;	85%
With copper(l) iodide; potassium carbonate; rac-diaminocyclohexane In 5,5-dimethyl-1,3-cyclohexadiene Reflux;

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C28H21Br → C52H36N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	84.7%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 3'-bromospiro[fluorene-9,9'-xanthene] → C49H30N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	84.7%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene] → C52H36N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	84.7%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-chloro-5-fluoro-1-bromo-3-(2-phenylpropan-2-yl)benzene → C39H28BrClN2

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃;	84%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C58H33ClN2 → C82H48N4

Conditions	Yield
With palladium diacetate; potassium carbonate In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	82.1%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 3-bromo-5-chloro-1,1’-biphenyl (126866-35-1) → C36H23ClN2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene for 6h; Reflux;	81%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C16H8F3NO3S2 → C39H23N3S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 130℃; for 3h;	80%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C21H11BrN2S → C45H26N4S

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 24h; Reflux;	80%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 3-bromobenzo[d]benzo[4,5]imidazolo[2,1-b]thiazole → C37H22N4S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	80%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 3-bromobenzo[4’,5’]imidazo[2’,1’:2,3]thiazolo[5,4-b]pyridine (1465269-57-1) → C36H21N5S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	80%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-(4-bromobenzenyl)-4,6-diphenyl-1,3,5-triazine (23449-08-3) → 11-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 80℃; for 24h; Inert atmosphere;	80%
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;	50%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 3-bromobiphenyl (2113-57-7) → C36H24N2

Conditions	Yield
With 1-dodecylbenzene; 3,5-ditertbutyl salicylic acid; copper; potassium carbonate for 18h; Inert atmosphere; Reflux;	80%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C33H20ClN3O → C57H35N5O

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;	80%

5-bromo-2-phenyl-1,3-thiazole (53715-67-6) + 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) → 2-phenyl-5-(12-phenylindolo[2,3-a]carbazole-11(12H)-yl)thiazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 160℃; for 48h;	79%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 2-chloro-4,6-diphenyl-1,3,5-triazine (3842-55-5) → 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole (1024598-01-3)

Conditions	Yield
Stage #1: 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 60℃; for 12h;	78%
Stage #1: 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 60℃; for 12h;	78%
Stage #1: 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole With sodium hydride In N,N-dimethyl-formamide for 1.16667h; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide for 4h;	54.6%
Stage #1: 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 20℃; for 0.5h; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide; paraffin oil at 20℃; for 7h;

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 4'-(4-bromo-phenyl)-[2,2';6',2'']terpyridine (89972-76-9) → C45H29N5

Conditions	Yield
With copper(l) iodide; 18-crown-6 ether; potassium carbonate at 175℃; for 36h; Inert atmosphere;	78%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + C30H16F3N5O3S → C53H31N7

Conditions	Yield
With 1,10-Phenanthroline; potassium carbonate; copper(I) bromide In toluene at 110 - 120℃; for 7h; Inert atmosphere;	76.2%

11,12-dihydro-11-phenylindolo[2,3-a]carbazole (1024598-06-8) + 5-bromo-2,4-di(pyridin-2-yl)thiazole → 5-(12-phenylindolo[2,3-a]carbazole-11(12H)-yl)-2,4-di(pyridine-2-yl)thiazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 160℃; for 48h;	76%

Upstream product

• 1361125-94-1 2-(2-nitrophenyl)-9-phenyl-9H-carbazole 
• 34673-74-0 2,2''-dinitro-p-terphenyl 
• 99770-93-1 benzene-1,4-diboronic acid bispinacol ester 
• 855180-11-9 9-phenyl-9H-carbazol-1-amine 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 577-19-5 2-nitrophenyl bromide 
• 1001911-63-2 (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid 
• 108-86-1 bromobenzene 
• 13716-12-6 tri-tert-butyl phosphine 
• 60511-85-5 11,12-dihydroindolo[2,3-a]carbazole 
• 591-50-4 iodobenzene 
• 222-19-5 indolo[2,3-a]carbazole 
• 765-87-7 cyclohexane-1,2-dione 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 939428-58-7 C₇₅H₄₅N₉ 
• 939428-56-5 C₅₈H₃₆N₆ 
• 1247053-53-7 C₃₅H₂₃N₃ 
• 1418184-60-7 C₄₂H₂₆N₂O 
• 222044-88-4 11,12-diphenyl-11,12-dihydro-indolo[2,3-a]carbazole 

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