3077-85-8

Basic information

• Product Name: 3-nitrocarbazole
• Synonyms: 3-nitrocarbazole;3-Nitro-9H-carbazole;9H-Carbazole, 3-nitro-;Brn 0185812;Ccris 6501;Einecs 221-367-5;Nsc 67708;INF 51
• CAS NO: 3077-85-8
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.20412
• EINECS: 221-367-5
• Mol File: 3077-85-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 216-217℃
• Boiling Point: 449℃
• Flash Point: 225℃
• Appearance: /
• Density: 1.435
• Vapor Pressure: 8.12E-08mmHg at 25°C
• Refractive Index: 1.795
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Ethanol (Slightly, Heated), Methanol (Very Slightly, Heated)
• PKA: 15.19±0.30(Predicted)
• CAS DataBase Reference: 3-nitrocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitrocarbazole(3077-85-8)
• EPA Substance Registry System: 3-nitrocarbazole(3077-85-8)

Safety Data

• Hazardous Substances Data: 3077-85-8(Hazardous Substances Data)

Usage

Uses

3-Nitrocarbazole is a nitrated polycyclic aromatic hydrocarbon (PAH) with mutagenic activity.

InChI:InChI=1/C12H8N2O2/c15-14(16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)13-12/h1-7,13H

Synthetic route

2-azido-5-nitrobiphenyl (91330-60-8) → 3-Nitro-carbazol (3077-85-8) + 2-amino-5-nitro-biphenyl (29608-75-1)

Conditions	Yield
With aluminium trichloride In dichloromethane Ambient temperature;	A 98% B 2%
With aluminium trichloride In dichloromethane Ambient temperature;	A 98% B n/a
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane Ambient temperature;	A 93% B 5%
With trifluorormethanesulfonic acid In dichloromethane Ambient temperature;	A 84% B 15%

1-(3-nitrocarbazol-9-yl)ethanone (89672-04-8) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;	96%

N-(p-toluenesulfonyl)-3-nitrocarbazole (92683-72-2) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;	96%

C14H16N2O2 → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
Stage #1: C14H16N2O2 With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II) In ethyl acetate at 70℃; under 760.051 Torr; for 2h; Sealed tube; Inert atmosphere; Stage #2: With oxygen In ethyl acetate at 70℃; under 760.051 Torr; for 24h; Sealed tube;	95%

6-nitro-2,3,4,9-tetrahydro-1H-carbazole (50823-86-4) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With copper(II) choride dihydrate In dimethyl sulfoxide at 100℃; for 24h;	90%
With chloranil In xylene for 6h; Heating;	35%
With chloranil; xylene

9H-carbazole (86-74-8) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With nitric acid; acetic acid at 60℃;	89.68%
With uronium nitrate In acetic acid for 10h;	86%
With nitric acid; acetic acid at 65℃; for 6h;	77%

1,2-Diiodobenzene (615-42-9) + 4-nitro-aniline (100-01-6) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With silver hexafluoroantimonate; chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I) In methanol at 0 - 80℃; for 24h; Inert atmosphere;	85%

4-ntrophenyl(phenyl)amine (836-30-6) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With air; potassium carbonate; Trimethylacetic acid; palladium diacetate at 110℃; for 14h;	76%
With palladium diacetate; potassium carbonate; Trimethylacetic acid Heating;

2-azido-5-nitrobiphenyl (91330-60-8) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
In decalin at 161℃; for 2h;	73%

9-(2-phenylsulphonyl-ethyl)-3-nitro-9H-carbazole (1058740-47-8) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20 - 50℃; for 8h;	73%

9H-carbazole (86-74-8) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9)

Conditions	Yield
With nitric acid In acetic acid at 50℃; for 3h;	A 69% B 31%
With copper nitrate hemi(pentahydrate); acetic anhydride; acetic acid at 60℃; for 0.75h;	A 64% B 15%
With ammonium cerium(IV) nitrate; silica gel In acetonitrile at 70 - 75℃;	A 61% B 19.5%

9H-carbazole (86-74-8) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9) + 3,6-dinitro-9H-carbazole (3244-54-0) + 1,6-dinitrocarbazole (3062-57-5)

Conditions	Yield
With nitric acid In acetic acid Product distribution; Heating;	A 68% B 27.1% C 49% D 23%
With ammonium cerium(IV) nitrate In acetonitrile at 90℃; for 6h;

3-nitrosocarbazole (40310-53-0) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With dihydrogen peroxide In potassium hydroxide; acetone for 1h; Ambient temperature; then reflux 1 h;	66%

5-Nitro-2,2'-diamino-biphenyl (91397-09-0) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
Stage #1: 5-Nitro-2,2'-diamino-biphenyl With tert.-butylnitrite In 1,2-dichloro-ethane for 0.166667h; Sealed tube; Stage #2: With oxygen In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;	50%

9-nitro-9H-carbazole (31438-20-7) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9)

Conditions	Yield
With lithium hydride In tetrahydrofuran for 3h; Heating;	A 47% B 20%
With lithium hydride In tetrahydrofuran for 1h;	A 47% B 20%
With nitric acid In acetic acid at 50℃; for 1h; Product distribution; other solvents, time, temp. and cat.;	A 33% B 14%

9H-carbazole (86-74-8) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9) + 3,6-dinitro-9H-carbazole (3244-54-0)

Conditions	Yield
With nitric acid In acetic acid at 60℃;	A 31% B 16% C 19%

1-(4-nitrophenyl)-1H-benzo[d][1,2,3]triazole (4490-51-1) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
In acetonitrile for 24h; UV-irradiation; Inert atmosphere;	17%

3-nitrosocarbazole (40310-53-0) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9)

Conditions	Yield
With sodium nitrite In acetic acid for 0.5h; Ambient temperature; then reflux 20 min.;	A 10% B 9%
With sodium nitrite In acetic acid for 0.5h; Ambient temperature; then reflux 20 min;	A 10% B 9%

9-nitroso-9H-carbazole (2788-23-0) → 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9) + 9H-carbazole (86-74-8)

Conditions	Yield
In benzene for 30h; irradiation;	A 9.7% B 3.7% C 7%
In benzene for 30h; irradiation;	A 9.7% B 3.7% C 7.04%
With peracetic acid In acetic acid at 25℃; for 24h; Yield given. Yields of byproduct given;
With sodium nitrite In acetic acid for 2h; Heating; Yield given. Yields of byproduct given;

2-iodo-4-nitrophenylamine (6293-83-0) + (2-bromophenyl)boronic acid (244205-40-1) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
Stage #1: 2-iodo-4-nitrophenylamine; (2-bromophenyl)boronic acid With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In toluene Stage #2: With sodium t-butanolate In toluene Further stages.;	4%

tetrachloromethane (56-23-5) + 9-nitroso-9H-carbazole (2788-23-0) → 3-Nitro-carbazol (3077-85-8) + 9H-carbazole (86-74-8)

3-nitro-9-nitroso-carbazole (5393-41-9) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With pentan-1-ol
Hydrolysis;
With potassium hydroxide

9-benzoyl-3-nitro-carbazole (101880-09-5) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
With potassium hydroxide

9-acetylcarbazole (574-39-0) → 2-nitrocarbazole (14191-22-1) + 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9)

Conditions	Yield
With alkaline acetone; nitric acid 1.) acetyl acid, heating, 5h; 2.) heating; Yield given. Multistep reaction. Yields of byproduct given;
With potassium hydroxide; nitric acid 1.) acetic anhydride, heating, 5h; 2.) methanol, heating, 0.5h; Yield given. Multistep reaction. Yields of byproduct given;

9-tosyl-9H-carbazole (3165-71-7) → 2-nitrocarbazole (14191-22-1) + 3-Nitro-carbazol (3077-85-8) + 1-nitro-9H-carbazole (31438-22-9) + 9H-carbazole (86-74-8)

Conditions	Yield
With potassium hydroxide; nitric acid 1.) acetic anhydride, 3.5h, heating; 2.) aceton, 3h, heating; Yield given. Multistep reaction. Yields of byproduct given;

5,6,7,8-tetrahydro-6-methoxy-3-nitro-9H-carbazole (155136-73-5) → 3-Nitro-carbazol (3077-85-8) + 3-nitro-6-methoxy-9H-carbazole (155136-79-1)

Conditions	Yield
With chloranil In xylene for 6h; Heating;	A 87.5 mg B 142 mg

nitric acid (7697-37-2) + 9H-carbazole (86-74-8) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
at 80 - 90℃;
at 80 - 90℃;

nitric acid (7697-37-2) + 9H-carbazole (86-74-8) + acetic acid (64-19-7) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
at 80℃;

nitric acid (7697-37-2) + 9H-carbazole (86-74-8) + nitrobenzene (98-95-3) → 3-Nitro-carbazol (3077-85-8)

Conditions	Yield
at 10 - 20℃;
at 10 - 20℃;

3-Nitro-carbazol (3077-85-8) → 3-nitro-N-chlorocarbazole

Conditions	Yield
With sodium hypochlorite In dichloromethane for 48h;	100%

3-Nitro-carbazol (3077-85-8) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-nitro-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 23℃; for 2h; Inert atmosphere;	99%

3-Nitro-carbazol (3077-85-8) + MeX → 9-methyl-3-nitro-9H-carbazole (61166-05-0)

Conditions	Yield
	97%

ethyl bromide (74-96-4) + 3-Nitro-carbazol (3077-85-8) → 9-ethyl-3-nitro-carbazole (86-20-4)

Conditions	Yield
Stage #1: 3-Nitro-carbazol With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: ethyl bromide In tetrahydrofuran for 0.166667h;	95%
With alkali

3-Nitro-carbazol (3077-85-8) → 3-amino-9H-carbazole (6377-12-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 80℃; for 24h; Inert atmosphere;	95%
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating;	84%
With palladium 10% on activated carbon; hydrazine hydrate In tetrahydrofuran; methanol; ethanol at 60℃; for 1.08333h;	74%

3-Nitro-carbazol (3077-85-8) + benzyl alcohol (100-51-6) → 9-benzyl-3-nitro-9H-carbazole (94127-10-3)

Conditions	Yield
With tributylphosphine; diamide In toluene at 40℃; for 15h;	95%

3-Nitro-carbazol (3077-85-8) + oxiranyl-methanol (556-52-5) → 3-nitro-9-oxiranylmethyl-9H-carbazole + C27H18N4O4

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 15h; Mitsunobu reaction;	A 95% B n/a

3-Nitro-carbazol (3077-85-8) + p-toluenesulfonyl chloride (98-59-9) → N-(p-toluenesulfonyl)-3-nitrocarbazole (92683-72-2)

Conditions	Yield
Stage #1: 3-Nitro-carbazol With tetrabutylammomium bromide; sodium hydride In dichloromethane for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane	94%
With potassium hydroxide In acetone Ambient temperature;	73%
With potassium hydroxide; acetone

3-Nitro-carbazol (3077-85-8) + N,N-tert-butoxycarbonyldehydroalanine (201338-62-7) → Boc-Ala[N-Boc-β-(3-nitrocarbazol-9-yl)]-OMe

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; Addition; Michael addition;	93%

3-Nitro-carbazol (3077-85-8) + benzyl bromide (100-39-0) → 9-benzyl-3-nitro-9H-carbazole (94127-10-3)

Conditions	Yield
Stage #1: 3-Nitro-carbazol With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: benzyl bromide In tetrahydrofuran for 0.166667h;	93%

3-Nitro-carbazol (3077-85-8) + Bromodiphenylmethane (776-74-9) → N-benzhydryl-3-nitrocarbazole (1454710-50-9)

Conditions	Yield
Stage #1: 3-Nitro-carbazol With tetrabutylammomium bromide; sodium hydride In dichloromethane for 0.166667h; Stage #2: Bromodiphenylmethane In dichloromethane for 0.5h;	92%

iodobenzene (591-50-4) + 3-Nitro-carbazol (3077-85-8) → 3-nitro-9-phenyl-9H-carbazole (121073-91-4)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In nitrobenzene at 200℃; for 12h;	90%
With potassium carbonate at 180℃; for 8h;	72%
With copper; potassium carbonate

3-Nitro-carbazol (3077-85-8) + bromo-triphenyl-methane (596-43-0) → N-trityl-3-nitrocarbazole (1454710-51-0)

Conditions	Yield
Stage #1: 3-Nitro-carbazol With tetrabutylammomium bromide; sodium hydride In dichloromethane for 0.166667h; Stage #2: bromo-triphenyl-methane In dichloromethane	90%

3-Nitro-carbazol (3077-85-8) + 4-iodo-biphenyl (1591-31-7) → 3-nitro-9-biphenylcarbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 12h;	89.7%

rac-octan-2-ol (4128-31-8) + 3-Nitro-carbazol (3077-85-8) → 9-(2-octyl)-3-nitro-9H-carbazole

Conditions	Yield
With (trimethyl-λ5-phosphanyliden)acetonitrile In toluene at 110℃; for 15h;	82%

3-Nitro-carbazol (3077-85-8) → 3-amino-5,6,7,8-tetrahydro-9H-carbazole (65796-52-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h; Inert atmosphere;	82%

3-Nitro-carbazol (3077-85-8) → 6-iodo-3-nitrocarbazole + 8-iodo-3-nitrocarbazole

Conditions	Yield
With N-iodo-succinimide; acetic acid at 25℃; for 2h;	A 15 % Chromat. B 80%

3-Nitro-carbazol (3077-85-8) + isopropyl bromide (75-26-3) → 9-isopropyl-3-nitro-9H-carbazole (22130-02-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 18h;	79%

3-Nitro-carbazol (3077-85-8) + 1-Bromo-4-fluorobenzene (460-00-4) → 9-(4-bromophenyl)-3-nitro-9H-carbazole

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24h;	77%

3-Nitro-carbazol (3077-85-8) + acetic anhydride (108-24-7) → 1-(3-nitrocarbazol-9-yl)ethanone (89672-04-8)

Conditions	Yield
With boron trifluoride diethyl etherate Heating;	72%
at 200 - 220℃;
With sulfuric acid

Upstream product

• 5393-41-9 3-nitro-9-nitroso-carbazole 
• 91330-60-8 2-azido-5-nitrobiphenyl 
• 86-74-8 9H-carbazole 
• 574-39-0 9-acetylcarbazole 
• 155136-73-5 5,6,7,8-tetrahydro-6-methoxy-3-nitro-9H-carbazole 
• 89672-04-8 1-(3-nitrocarbazol-9-yl)ethanone 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 120-72-9 indole 
• 496-15-1 1-indoline 
• 99-54-7 3,4-dichloronitrobenzene 
• 62-53-3 aniline 
• 615-42-9 1,2-Diiodobenzene 

Downstream Products

• 87353-57-9 9-(Ethoxy-phenyl-methyl)-3-nitro-9H-carbazole 
• 5393-41-9 3-nitro-9-nitroso-carbazole 
• 83277-37-6 2-[1-Benzyl-2-(3-nitro-carbazol-9-yl)-2-oxo-ethyl]-isoindole-1,3-dione 
• 94127-10-3 9-benzyl-3-nitro-9H-carbazole 
• 22130-02-5 3-nitro-9-isopropylcarbazole 
• 65796-52-3 3-amino-5,6,7,8-tetrahydro-9H-carbazole 

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Carbazole and its derivatives were nitrated using cupric nitrate in the presence of acetic acid and acetic anhydride. Under these conditions, carbazole is nitrated to 3-nitrocarbazole, and N-alkylcarbazoles are nitrated to 3.6-dinitro derivatives.

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