-
Name
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one
- EINECS 604-791-9
- CAS No. 15128-52-6
- Article Data71
- CAS DataBase
- Density 1.275 g/cm3
- Solubility
- Melting Point 224-226 ºC
- Formula C12H11NO
- Boiling Point 386.3 ºC at 760 mmHg
- Molecular Weight 185.225
- Flash Point 194.5 ºC
- Transport Information
- Appearance white crystal powder
- Safety 26-36
- Risk Codes 36/37/38
-
Molecular Structure
-
Hazard Symbols
Xi
- Synonyms Carbazol-4(1H)-one,2,3-dihydro- (6CI,7CI,8CI);1,2,3,4-Tetrahydrocarbazol-4-one;1,2-Dihydro-4(3H)-carbazolone;2,3-Dihydrocarbazol-4(1H)-one;4-Oxo-1,2,3,4-tetrahydrocarbazole;
- PSA 32.86000
- LogP 2.68690
Synthetic route
-
-
85239-68-5
3-[(2-iodophenyl)amino]cyclohex-2-en-1-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With tetrabutyl-ammonium chloride; sodium acetate; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 0.5h; Heck reaction; Irradiation; | 95% |
| With potassium hydroxide; copper(l) iodide; L-proline In dimethyl sulfoxide at 90℃; for 24h; | 92% |
| With cyclodextrin-grafted silica-supported Pd nanoparticles at 100℃; for 1h; Heck Reaction; Green chemistry; | 85% |
-
-
1172640-24-2
methyl 6-(2-nitrophenyl)-5-oxohexanoate
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With hydrogenchloride; iron In water at 110℃; for 0.333333h; Inert atmosphere; | 92% |
-
-
942-01-8
1,2,3,4-tetrahydrocarbazole
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; water at 0℃; | 91% |
| With nitrosonium perchlorate In water; acetonitrile for 1h; | 79% |
| With 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In water; acetonitrile for 1h; Mechanism; Product distribution; other indole derivatives and nitrosonium salts, var. solvents; | 71% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With hydrogenchloride; titanium(III) chloride In acetone at 22℃; for 16h; Reagent/catalyst; Temperature; Solvent; | 91% |
-
-
128266-89-7
cyclohexane-1,3-dione monophenylhydrazone
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In acetic acid for 3h; Heating; | 90% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h; Cooling with ice; | 90% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid for 24h; Reflux; Inert atmosphere; | 90% |
-
-
942-01-8
1,2,3,4-tetrahydrocarbazole
-
A
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
B
-
3456-99-3
1-oxo-2,3,4,9-tetrahydrocarbazole
| Conditions | Yield |
|---|---|
| With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; water at 0 - 20℃; for 5.5h; | A 89% B 2% |
-
-
59-88-1
phenylhydrazine hydrochloride
-
-
504-02-9
1,3-cylohexanedione
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With 1-(3-sulfopropyl)pyridinium p-toluenesulfonate In water at 100℃; for 0.25h; | 89% |
| Stage #1: phenylhydrazine hydrochloride; 1,3-cylohexanedione In acetonitrile at 80 - 85℃; Fischer Indole Synthesis; Stage #2: With hydrogenchloride In water at 90 - 95℃; Fischer Indole Synthesis; | 18% |
-
-
29873-09-4
4-(1H-indol-2-yl)butanoic acid
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In water; toluene for 12h; Reflux; Inert atmosphere; | 88% |
-
-
138040-05-8
3-hydroxy-2-(2-nitrophenyl)cyclohex-2-enone
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With iron; acetic acid for 2.5h; Reflux; | 86% |
-
-
134256-40-9
2-(o-bromophenyl)cyclohexane-1,3-dione
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With 1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium(0); <3THF*Mg2Cl2O*TiNCO> at 100℃; for 12h; | 85% |
| With tetrakis(triphenylphosphine) palladium(0); <3THF*Mg2Cl2O*TiNCO> In various solvent(s) at 100℃; for 12h; Heating; | 85% |
-
-
24706-50-1
3-phenylaminocyclohex-2-enone
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With copper diacetate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | 85% |
| With copper diacetate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | 85% |
| With silver hexafluoroantimonate; [hydroxy(tosyloxy)iodo]benzene In 1,2-dichloro-ethane at 90℃; for 12h; Sealed tube; | 80% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 100℃; under 4560 Torr; for 90h; | 83% |
-
-
14088-61-0
2-diazocyclopentanone
-
-
529-23-7
2-aminobenzaldehyde
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With dirhodium tetraacetate; diphenyl hydrogen phosphate In 1,2-dichloro-ethane at 80℃; Catalytic behavior; Reagent/catalyst; Solvent; Molecular sieve; | 83% |
-
-
68890-19-7
3-(2-bromoanilino)-cyclohex-2-en-1-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With triethylamine; tetrakis(triphenylphosphine) palladium(0) In ethanol at 80℃; for 48h; Product distribution / selectivity; | 82% |
| With copper(l) iodide; sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 170℃; for 3h; | 80% |
| With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate at 140℃; for 2h; | 77% |
-
-
176042-31-2
2′-nitro-4,5-dihydro-[1,1′-biphenyl]-2(3H)-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With hydrogenchloride; titanium(III) chloride In acetone at 22℃; for 16h; | 82% |
| With 1,10-Phenanthroline; carbon monoxide; 1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; under 4560 Torr; | 74% |
| With carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; under 4560 Torr; for 24h; | 74% |
| Multi-step reaction with 2 steps 1: titanium(III) chloride; hydrogenchloride / acetone / 1 h / 22 °C 2: titanium(III) chloride; hydrogenchloride / acetone / 16 h / 22 °C View Scheme |
-
-
27385-45-1
cyclohexane-1,3-dione monophenylhydrazone
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid for 16h; Heating; | 80% |
| With sulfuric acid at 0℃; | 30% |
| With sulfuric acid; water |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With silver hexafluoroantimonate In 1,2-dichloro-ethane at 90℃; for 5h; Sealed tube; | 77% |
-
-
504-02-9
1,3-cylohexanedione
-
-
100-63-0
phenylhydrazine
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium hydrogensulfate In water at 100℃; for 4h; Fischer indole synthesis; | 70% |
| With trifluoroacetic acid at 140℃; for 0.166667h; Microwave irradiation; | 40% |
| With trifluoroacetic acid at 140℃; for 0.166667h; Fischer Indole Synthesis; Microwave irradiation; | 40% |
-
-
27385-45-1
cyclohexane-1,3-dione monophenylhydrazone
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid Heating; | 65% |
| With acetic acid; zinc(II) chloride for 4.5h; Heating; |
-
-
78839-84-6
2,2,2-Trifluoro-N-[2-(6-oxo-cyclohex-1-enyl)-phenyl]-acetamide
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium hydroxide In tetrahydrofuran; methanol for 12h; Ambient temperature; | 61% |
| With sodium hydroxide In methanol for 12h; Ambient temperature; | 60% |
-
-
176042-30-1
3-methoxy-2-(2-nitrophenyl)-2-cyclohexen-1-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 120℃; under 4560 Torr; for 96h; | 61% |
-
-
56671-81-9
3-bromo-2-cyclohexen-1-one
-
-
615-43-0
2-iodophenylamine
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| Stage #1: 3-bromo-2-cyclohexen-1-one; 2-iodophenylamine With copper(l) iodide; triethylamine In dimethyl sulfoxide at 60℃; for 2h; Ullmann-Goldberg Substitution; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0) In dimethyl sulfoxide at 120℃; for 24h; | 60% |
-
-
903906-68-3
(1E)-1,3-cyclohexanedione 1-(phenylhydrazone)
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid at 20℃; for 8h; Heating / reflux; | 58% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sulfuric acid | 51% |
-
-
73554-47-9
6-Oxo-10-(2-aminomethyl)-6,7,8,9-tetrahydro-pyrido(1,2-a)indole
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| In methanol for 16h; Irradiation; | 44% |
-
A
-
942-01-8
1,2,3,4-tetrahydrocarbazole
-
B
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 2h; | A 22% B 43% |
-
-
51409-83-7
9-bromo-4,4-dimethyl-2-(naphthalen-1-yl)-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium acetate; tetraphenyl phosphonium chloride; dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 150℃; for 20h; Product distribution / selectivity; | 36% |
-
-
124907-00-2
3-[(2-fluorophenyl)amino]cyclohex-2-en-1-one
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| Stage #1: 3-[(2-fluorophenyl)amino]cyclohex-2-en-1-one With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at 75℃; for 2.5h; Stage #2: With acetic acid In tetrahydrofuran; cyclohexane at 20℃; for 0.5h; | 33% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
98-09-9
benzenesulfonyl chloride
-
-
104876-54-2
9-(phenylsulfonyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With dmap; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; | 98% |
| With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 2h; Ambient temperature; | 62% |
| With sodium hydride 1.) DMF, 0 deg C, 2.) DMF, r.t., 3 h; Yield given. Multistep reaction; |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
100-39-0
benzyl bromide
-
-
41175-05-7
9-phenylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 96% |
| With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; | 95% |
| With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 95% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
24424-99-5
di-tert-butyl dicarbonate
-
-
1451144-14-1
tert-butyl 4-oxo-1,2,3,4-tetrahydro-9H-carbazole-9-carboxylate
| Conditions | Yield |
|---|---|
| With dmap In dichloromethane at 20℃; for 0.25h; | 96% |
| Stage #1: 1,2,3,9-tetrahydro-4H-carbazol-4-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 0 - 20℃; for 2.25h; | 95% |
| Stage #1: 1,2,3,9-tetrahydro-4H-carbazol-4-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; | 90% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; silver trifluoroacetate; toluene-4-sulfonic acid In water at 60℃; for 0.666667h; regioselective reaction; | 94% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
74-88-4
methyl iodide
-
-
27387-31-1
9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| Stage #1: 1,2,3,9-tetrahydro-4H-carbazol-4-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; | 93% |
| With sodium hydride In N,N-dimethyl-formamide | 65% |
| With sodium hydride 1.) DMF, 0-5 deg C, 1 h, 2.) DMF, a) 0-5 deg C, 3 h, b) RT, 15 h; Yield given. Multistep reaction; |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
65342-65-6
4,4-Dideuterio-1,2,3,4-tetrahydro-carbazol
| Conditions | Yield |
|---|---|
| With lithium aluminium deuteride In tetrahydrofuran for 24h; | 92% |
-
-
64-67-5
diethyl sulfate
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
73825-22-6
9-ethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium hydroxide In acetone for 2.5h; Heating; | 91% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
14362-50-6
s-trans-anti-1,2,3,4-tetrahydrocarbazol-4-one
| Conditions | Yield |
|---|---|
| With pyridine; hydroxylamine hydrochloride at 20℃; | 91% |
| With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 24h; Reflux; Inert atmosphere; | 80% |
| With hydroxylamine hydrochloride In ethanol; water for 12h; Darkness; | |
| With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 24h; Reflux; Inert atmosphere; | 1.73 g |
| With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 6h; |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
52602-39-8
9H-carbazol-4-ol
| Conditions | Yield |
|---|---|
| palladium on activated charcoal In diphenylether at 250℃; for 18h; | 90% |
| With sodium hydroxide; nickel In water for 20h; Heating / reflux; | 50% |
| With 1% Pd/C In 1,3,5-trimethyl-benzene Heating; | 46% |
| With palladium on activated charcoal at 270℃; | |
| With 1-dodecene; palladium on activated charcoal In Triethylene glycol dimethyl ether Heating; |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
77-78-1
dimethyl sulfate
-
-
27387-31-1
9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 60 - 70℃; for 2h; | 89% |
| In acetone at 20℃; for 1h; | 83% |
| With potassium carbonate | |
| With potassium hydroxide; water; acetone |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
459-46-1
4-Fluorobenzyl bromide
-
-
886434-61-3
9-(4-fluorobenzyl)-1,2,3,9-tetrahydrocarbazol-4-one
| Conditions | Yield |
|---|---|
| With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h; | 83% |
-
-
15128-52-6
1,2,3,9-tetrahydro-4H-carbazol-4-one
-
-
79-19-6
thiosemicarbazide
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water at 20℃; for 3h; | 81% |
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one Chemical Properties
The Molecular Structure of 1,2,3,9-Tetrahydro-4(H)-carbazol-4-one (CAS NO.15128-52-6):
Systematic Name: 1,2,3,9-Tetrahydro-4H-carbazol-4-one
Empirical Formula: C12H11NO
Molecular Weight: 185.2218
Product Categories: Miscellaneous; (intermediate of carvedilol and ondansetron); Heterocyclic Compounds; Heterocycles
Appearance: white powder
Nominal Mass: 185
Average Mass: 185.2218
Monoisotopic Mass: 185.084064
Index of Refraction: 1.689
Molar Refractivity: 55.44 cm3
Molar Volume: 145.1 cm3
Surface Tension: 59.9 dyne/cm
Density: 1.275 g/cm3
Flash Point: 194.5 °C
Enthalpy of Vaporization: 63.52 kJ/mol
Boiling Point: 386.3 °C at 760 mmHg
Melting Point: 224-226 °C
Vapour Pressure: 3.59E-06 mmHg at 25 °C
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one Uses
It can be used as a carbazole derivative with antimycobacterial activity.
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one Safety Profile
Hazard Codes: 
Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one Specification
1,2,3,9-Tetrahydro-4(H)-carbazol-4-one (CAS NO.15128-52-6) is also called as Rarechem ak ma k053 ; 4-Oxo-1,2,3,4-tetrahydrocarbazole ; 1,2,3,4-Tetrahydro-4h-carbazole-4-one ; 1,2,3,4-Tetrahydro-4-oxo-carbazole ; 1,2,3,4-Tetrahydro-9h-carbazole-4-one ; 1,2,3,9-Tetrahydro-4(h)-carbazol-4-one ; 1,2,3,9-Tetrahydro-9[h]-carbazole-4-one .
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