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Product Details
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Chemical Properties |
White to light yellow solid |
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Uses |
3-Bromocarbazole is used as a intermediate for organic light-emitting diode(OLED) and pharmaceutical. |
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Preparation |
3-Bromocarbazole synthesis: A solution of N-bromosuccinimide (1.1g, 5.98mmol) in dimethylformamide was added dropwise to a solution of carbazole (1, 1g, 5.96mmol) in dimethylformamide (15mL) at 0°C. The reaction mixture was then stirred at room temperature for 24h. The reaction was poured into distilled water to give a cream coloured precipitate. The precipitate was filtered off under vacuum and washed with distilled water (3 × 20mL). The precipitate was dissolved in ethyl acetate, dried with sodium sulfate and filtered. Upon concentration under reduced pressure the crude product was obtained as a brown solid. After crystallisation of the crude product with chloroform, the pure 3-Bromo-9H-carbazole(692 mg, 47%) was obtained as white crystals. Rf (ethyl acetate/hexane, 1:6 v/v): 0.43; melting point: 200–201°C. |
Isomeric SMILES: C1=CC=C2C(=C1)C3=C(N2)C=CC(=C3)Br
InChIKey: LTBWKAYPXIIVPC-UHFFFAOYSA-N
InChI: InChI=1S/C12H8BrN/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7,14H
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9H-carbazole
3-bromo-9H-carbazole
3,6-dibromo-9H-carbazole
| Conditions | Yield |
|---|---|
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;
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47% |
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With N-Bromosuccinimide; silica gel; In dichloromethane; at 18 ℃; for 0.33h; Product distribution; one to four equivalents of NBS, other times; other N-heterocycles;
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With tetra-N-butylammonium tribromide; In chloroform; for 0.5h; Product distribution; Ambient temperature; other reaction times, different substrate/reagent ratios;
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62 % Chromat. 17 % Chromat. |
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With tetra-N-butylammonium tribromide; In chloroform; for 0.5h; Product distribution; Ambient temperature; other reaction times, different substrate/reagent ratios, electrolysis;
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With N-Bromosuccinimide; silica gel; In dichloromethane; at 18 ℃; for 0.33h; Yield given. Yields of byproduct given;
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With tetra-N-butylammonium tribromide; In chloroform; for 0.5h; Ambient temperature;
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17 % Chromat. 62 % Chromat. |
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9H-carbazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h;
With chloro-trimethyl-silane; In tetrahydrofuran; hexane; at 20 ℃; for 3h;
With bromine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;
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9H-carbazole
3-bromo-9H-carbazole
| Conditions | Yield |
|---|---|
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With N-Bromosuccinimide; In dichloromethane;
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98% |
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With N-Bromosuccinimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;
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98% |
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With bromine; In dichloromethane; at 0 - 30 ℃; for 0.5h; Temperature; Darkness;
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98.2% |
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With N-Bromosuccinimide; In N,N-dimethyl acetamide; at 5 ℃;
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97% |
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With N-Bromosuccinimide; In tetrahydrofuran; at 25 ℃;
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95% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at -10 ℃; Inert atmosphere;
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95% |
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With silica-supported quinolinium tribromide; In acetonitrile; at 20 ℃; for 5h; regioselective reaction;
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94% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;
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94% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
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92% |
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With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
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91% |
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With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 4h; Inert atmosphere; Schlenk technique;
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90% |
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With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20 ℃; for 17.5h; Inert atmosphere; Schlenk technique; Cooling with ice;
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89% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide;
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88% |
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With hydrogen bromide; dimethyl sulfoxide; at 50 ℃; for 2h;
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87% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide;
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86% |
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With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 5h;
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86.1% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
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85% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; Cooling with ice;
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85% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;
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85% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 ℃; Darkness;
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78% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 8h; regioselective reaction; Darkness; Inert atmosphere;
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76% |
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With tetrabutylammomium bromide; copper(ll) bromide; In ethanol; at 25 ℃; regioselective reaction;
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76% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;
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75% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;
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75% |
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With Oxone; copper(ll) bromide; In acetonitrile; at 20 ℃; for 3h; regioselective reaction;
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73% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;
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72% |
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With N-Bromosuccinimide; silica gel; In dichloromethane; at 10 - 20 ℃; for 42h;
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71% |
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With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 24h;
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70% |
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9H-carbazole; With n-butyllithium; In diethyl ether; at -78 - 20 ℃;
With trimethyltin(IV)chloride; In diethyl ether; at -78 ℃; for 24h;
With bromine; In diethyl ether; at -78 - 20 ℃; for 2h; Further stages.;
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69% |
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With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃;
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69% |
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With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 1h;
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68% |
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With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 1h;
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68% |
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With N-Bromosuccinimide; In acetic acid monohydrate; at 20 ℃; for 15h;
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67% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at -10 - -5 ℃;
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67.6% |
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With N-Bromosuccinimide; In dichloromethane; acetone; at 20 ℃; for 24h;
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62% |
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With N-Bromosuccinimide; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;
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59% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 ℃; for 12h;
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58.04% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 ℃; for 12h;
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58.04% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 13h;
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58% |
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With N-Bromosuccinimide; In tert-butyl methyl ether; at 100 ℃; for 12h; Sealed tube;
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56% |
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With N-Bromosuccinimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere;
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55% |
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With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 16h;
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53% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 ℃;
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51% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;
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51.9% |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;
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47% |
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With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 21h;
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45% |
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With bromine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 21h;
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35% |
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With potassium bromate; hydrogenchloride; acetic acid; potassium bromide;
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With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide;
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With pyridine; bromine;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;
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With N-Bromosuccinimide; In dichloromethane; Inert atmosphere;
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With pyridine; bromine; at 0 ℃; for 2h;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;
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With N-Bromosuccinimide; In chloroform;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;
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20 g |
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With N-Bromosuccinimide; In dichloromethane; for 6h;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;
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With Sodium orthovanadate; vanadium dependent haloperoxidase from Acaryochloris marina MBIC 11017; Flavin mononucleotide; potassium bromide; In acetonitrile; at 20 ℃; for 16h; pH=6; Irradiation; Enzymatic reaction;
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95 %Chromat. |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h;
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;
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6-bromo-1,2,3,4-tetrahydro-9H-carbazole
1-(3-bromo-9H-carbazol-9-yl)ethan-1-one
9-benzyl-9H-carbazole
(3-bromo-9H-carbazol-9-yl)(phenyl)methanone
(3-bromo-9H-carbazol-9-yl)(phenyl)methanone
3-Hydroxycarbazol
9H-carbazole-3-carboxylic acid
3-methoxycarbazole
CAS:15155-41-6
Molecular Formula:C6H2Br2N2S
Molecular Weight:293.97
CAS:16807-13-9
