203-65-6

Basic information

• Product Name: 4,5-epiminophenanthrene
• Synonyms: 4,5-epiminophenanthrene;4H-Benzo[def]carbazole;4,5-Iminophenanthrene;Einecs 205-906-1;VQOUCGZKKPJLGH-UHFFFAOYSA-N
• CAS NO: 203-65-6
• Molecular Formula: C₁₄H₉N
• Molecular Weight: 191.22796
• EINECS: 205-906-1
• Product Categories: Pharmaceutical intermediates
• Mol File: 203-65-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 173-174 °C(Solv: Do not display any solvent name:::mixture (No Ma-tc-h))
• Boiling Point: 391.2 °C at 760 mmHg
• Flash Point: 177.5 °C
• Appearance: /
• Density: 1.363 g/cm³
• Vapor Pressure: 5.64E-06mmHg at 25°C
• Refractive Index: 1.932
• PKA: 17.00±0.30(Predicted)
• CAS DataBase Reference: 4,5-epiminophenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-epiminophenanthrene(203-65-6)
• EPA Substance Registry System: 4,5-epiminophenanthrene(203-65-6)

Safety Data

• Hazardous Substances Data: 203-65-6(Hazardous Substances Data)

Usage

Uses

4,5-Iminophenanthrene is one of the volatile components found in tobacco smoke, and is also a suspected carcinogen.

InChI:InChI=1/C14H9N/c1-3-9-7-8-10-4-2-6-12-14(10)13(9)11(5-1)15-12/h1-8,15H

Synthetic route

8,9-dihydro-4H-benzocarbazole (5691-00-9) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 110℃; for 6h;	91%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 110℃; for 6h;	91%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 110℃; for 6h;	91%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 20 - 110℃; for 6h;	90%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 110℃; for 6h;	90%

4-phenanthrenamine (17423-48-2) → phenanthrene (85-01-8) + cyclopentaphenanthrene (203-65-6)

Conditions	Yield
With calcium oxide at 560℃; for 0.666667h;	A 12% B 60%

4-phenanthrenamine (17423-48-2) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
With calcium oxide at 400℃; im Stickstoff-Strom;

9,10-dihydrophenanthrene (776-35-2) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 12 h / 50 °C 2: nitric acid; sulfuric acid / dichloromethane 3: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 4: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 20 - 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 20 - 110 °C View Scheme
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 12 h / 50 °C 2: sulfuric acid; nitric acid / dichloromethane / 6 h / 20 - 30 °C 3: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 4: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid; N-Bromosuccinimide / acetonitrile / 12 h / 50 °C 2: sulfuric acid; nitric acid / dichloromethane / 6 h / 30 °C 3: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 4: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 12 h / 50 °C 2: nitric acid; sulfuric acid / dichloromethane / 6 h / 30 °C 3: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 4: palladium on activated charcoal; hydrazine / ethanol / 24 h / 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 12 h / 50 °C 2: nitric acid; sulfuric acid / dichloromethane / 6 h / 30 °C 3: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 4: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 5: sodium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 6 h / 110 °C View Scheme

C14H9Br2N (61650-86-0) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / dichloromethane 2: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 3: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 20 - 50 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 20 - 110 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / dichloromethane / 6 h / 20 - 30 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 3: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / dichloromethane / 6 h / 30 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 3: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / dichloromethane / 6 h / 30 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 3: palladium on activated charcoal; hydrazine / ethanol / 24 h / 50 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / dichloromethane / 6 h / 30 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 3: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 4: sodium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 6 h / 110 °C View Scheme

2,7-dibromo-4-nitro-9,10-dihydro-phenanthrene (1256095-16-5) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 2: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 20 - 50 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 20 - 110 °C View Scheme
Multi-step reaction with 3 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 2: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 2: palladium on activated charcoal; hydrazine / ethanol / 24 h / 50 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 3 h / 180 °C 2: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 3: sodium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 6 h / 110 °C View Scheme

4,8-dibromo-2,6-dihydro-1H-benzo[def]carbazole (1256095-17-6) → cyclopentaphenanthrene (203-65-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 20 - 50 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; oxygen / toluene / 6 h / 20 - 110 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite / toluene / 6 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrazine / ethanol / 24 h / 50 °C 2: sodium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 6 h / 110 °C View Scheme

1-Bromo-3-iodobenzene (591-18-4) + cyclopentaphenanthrene (203-65-6) → C20H12BrN

Conditions	Yield
With copper(l) iodide; 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h;	91%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 12h; Reflux;	80%

2-chloro-4-phenylquinazoline (29874-83-7) + cyclopentaphenanthrene (203-65-6) → C28H17N3

Conditions	Yield
With copper; potassium carbonate In nitrobenzene at 200℃; for 12h; Inert atmosphere;	84%

iodobenzene (591-50-4) + cyclopentaphenanthrene (203-65-6) → C20H13N

Conditions	Yield
With copper; potassium carbonate In nitrobenzene at 200℃; for 12h; Inert atmosphere;	84%

1,4-bromoiodobenzene (589-87-7) + cyclopentaphenanthrene (203-65-6) → C20H12BrN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 12h; Reflux;	84%

cyclopentaphenanthrene (203-65-6) → 1,3,5,7-tetrabromo-4H-benzocarbazole (5783-21-1)

Conditions	Yield
With bromine In tetrachloromethane for 1h; Ambient temperature;	83%

cyclopentaphenanthrene (203-65-6) → 8,9-dihydro-4H-benzocarbazole (5691-00-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethanol under 735.5 Torr; for 20h; Ambient temperature;	82%
With ethanol; sodium

cyclopentaphenanthrene (203-65-6) + 3-chloro-(4,6-diphenyl-1,3,5-triazin-2-yl)benzene → C35H22N4

Conditions	Yield
With copper; potassium carbonate In nitrobenzene at 200℃; for 12h; Inert atmosphere;	82%

2-bromodibenzo[b,d]furan (86-76-0) + cyclopentaphenanthrene (203-65-6) → C26H15NO

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 15h; Inert atmosphere; Reflux;	80%

biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine (1246562-40-2) + cyclopentaphenanthrene (203-65-6) → C47H34N2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	79%
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	79%

4,4'-diiodobiphenyl (3001-15-8) + cyclopentaphenanthrene (203-65-6) → C40H24N2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	75%

1.4-dibromobenzene (106-37-6) + cyclopentaphenanthrene (203-65-6) → C34H20N2

Conditions	Yield
With potassium phosphate; tri-tert-butyl phosphine; palladium diacetate In toluene for 12h; Heating;	75%

bromobenzene (108-86-1) + cyclopentaphenanthrene (203-65-6) → C20H13N

Conditions	Yield
With copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 24h;	75%

C19H6Br2F3N3 + cyclopentaphenanthrene (203-65-6) → C47H22F3N5

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 24h; Inert atmosphere;	75%

3-bromo-4'-chloro-1,1'-biphenyl (164334-69-4) + cyclopentaphenanthrene (203-65-6) → C26H16ClN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; XPhos In toluene at 105 - 110℃; for 16h; Inert atmosphere;	73%

cyclopentaphenanthrene (203-65-6) → C14H7Br2N

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	72%
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	55%
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	55%

1.4-dibromobenzene (106-37-6) + cyclopentaphenanthrene (203-65-6) → C20H12BrN

Conditions	Yield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; 18-crown-6 ether; potassium carbonate for 8h; Heating;	70%

C38H25BrN4 + cyclopentaphenanthrene (203-65-6) → C52H33N5

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	70%

2-(4'-bromophenyl)-4,6-diphenylpyridine (3557-70-8) + cyclopentaphenanthrene (203-65-6) → C37H24N2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	69%

C34H23BrN2 + cyclopentaphenanthrene (203-65-6) → C48H31N3

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	67%

C28H18BrN3 + cyclopentaphenanthrene (203-65-6) → C42H26N4

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	67%

7-bromo-1-chloronaphthalene (90947-99-2) + cyclopentaphenanthrene (203-65-6) → C24H14ClN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; XPhos In toluene at 105 - 110℃; for 16h; Inert atmosphere;	67%

C28H19BrN2 + cyclopentaphenanthrene (203-65-6) → C42H27N3

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	65%

cyclopentaphenanthrene (203-65-6) + 2-halo-4,6-bis(4,6-diphenylpyridin-2-yl)-1,3,5-triazine → C51H32N6

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	65%

3-bromo-1-chloronaphthalene (325956-47-6) + cyclopentaphenanthrene (203-65-6) → C24H14ClN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; XPhos In toluene at 105 - 110℃; for 16h; Inert atmosphere;	56%

3,7-dibromodibenzo[b,d]furan (67019-91-4) + cyclopentaphenanthrene (203-65-6) → C26H14BrNO

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 110℃; for 10h; Inert atmosphere;	55%

1-Chloro-4-iodobenzene (637-87-6) + cyclopentaphenanthrene (203-65-6) → C20H12ClN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; XPhos In toluene at 105 - 110℃; for 16h; Inert atmosphere;	53%

2,7-dibromo-9,9-dimethyl-9H-fluorene (28320-32-3) + cyclopentaphenanthrene (203-65-6) → C29H20BrN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; XPhos In toluene at 105 - 110℃; for 10h; Inert atmosphere;	53%

cyclopentaphenanthrene (203-65-6) → C14H8BrN

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	50%
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	45%
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 0.5h;	45%

Upstream product

• 17423-48-2 4-phenanthrenamine 
• 1244651-37-3 N-(3-bromo-2-iodophenyl)-2-hydroxy-2-methylpropanamide 
• 5691-00-9 8,9-dihydro-4H-benzocarbazole 
• 1256095-17-6 4,8-dibromo-2,6-dihydro-1H-benzo[def]carbazole 
• 1256095-16-5 2,7-dibromo-4-nitro-9,10-dihydro-phenanthrene 
• 61650-86-0 C₁₄H₉Br₂N 
• 776-35-2 9,10-dihydrophenanthrene 

Downstream Products

• 74234-55-2 4-benzoyl-4H-benzocarbazole 

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