Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran at 85℃; for 48h; | 98% |
With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at 20℃; | 97% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In ethanol at 20 - 25℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 24h; | A 47% B n/a |
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; | |
With tetra-N-butylammonium tribromide In chloroform for 0.5h; Product distribution; Ambient temperature; other reaction times, different substrate/reagent ratios; | A 62 % Chromat. B 17 % Chromat. |
Conditions | Yield |
---|---|
With bromine In diethyl ether | 85% |
With N-Bromosuccinimide In dichloromethane for 1h; Irradiation; | 84.6% |
9H-carbazole
A
3,6-dibromo-9H-carbazole
B
1,3,6-tribromo-9H-carbazole
C
1,3,6,8-tetrabromo-9-methyl-9H-carbazole
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 72h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 2: 81 percent / ethanol / 1 h / 70 °C 3: NaCl / acetonitrile / Photolysis View Scheme |
bis(4-bromophenyl)amine
3,6-dibromo-9H-carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 2: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 3: 81 percent / ethanol / 1 h / 70 °C 4: NaCl / acetonitrile / Photolysis View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Br2 / CH2Cl2 / 8 h / Heating 2: 23.44 g / KOH / ethanol; H2O / 1.5 h / Heating 3: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 4: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 5: 81 percent / ethanol / 1 h / 70 °C 6: NaCl / acetonitrile / Photolysis View Scheme |
N,N-bis-(4-bromophenyl)benzamide
3,6-dibromo-9H-carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 23.44 g / KOH / ethanol; H2O / 1.5 h / Heating 2: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 3: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 4: 81 percent / ethanol / 1 h / 70 °C 5: NaCl / acetonitrile / Photolysis View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / ethanol / 1 h / 70 °C 2: NaCl / acetonitrile / Photolysis View Scheme |
B
3,6-dibromo-9H-carbazole
C
bis(4-bromophenyl)amine
Conditions | Yield |
---|---|
With sodium chloride In acetonitrile Photolysis; | A 6.8 mg B n/a C n/a |
9-benzoyl-3,6-dibromo-carbazole
3,6-dibromo-9H-carbazole
Conditions | Yield |
---|---|
With potassium hydroxide |
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
9H-carbazole
3,6-dibromo-9H-carbazole
Conditions | Yield |
---|---|
With tetrachloromethane |
bromine
acetic anhydride
9H-carbazole
acetic acid
3,6-dibromo-9H-carbazole
hydrogenchloride
N-nitroso-3,6-dibromocarbazole
3,6-dibromo-9H-carbazole
3,6-dibromo-9H-carbazole
1-bromo-octane
3,6-dibromo-9-octyl-9H-carbazole
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In toluene at 120℃; | 100% |
With tetrabutylammomium bromide; potassium hydroxide In acetone for 6h; Reflux; | 95% |
With tetrabutylammomium bromide; potassium hydroxide In water; toluene for 24h; Heating; | 95% |
3,6-dibromo-9H-carbazole
4-Fluoronitrobenzene
3,6-dibromo-9-(4-nitrophenyl)-9H-carbazole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
With potassium carbonate In N,N-dimethyl-formamide for 12h; Reflux; | 81% |
With potassium tert-butylate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; | 80% |
3,6-dibromo-9H-carbazole
(R)-glycidyl nosylate
(-)-(S)-3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole
Conditions | Yield |
---|---|
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere; | 100% |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; Cooling with ice; |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
3,6-dibromo-9H-carbazole
copper(I) cyanide
9H-carbazole-3,6-dicarbonitrile
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 70h; Heating; | 99% |
1-bromo-butane
3,6-dibromo-9H-carbazole
3,6-dibromo-(N-n-butyl)carbazole
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With sodium hydroxide In acetone at 60℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-butane In acetone Reflux; Inert atmosphere; | 99% |
With tetrabutylammomium bromide; potassium hydroxide In water; toluene for 5h; Reflux; | 82% |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene at 100℃; for 2h; Alkylation; | 75% |
3,6-dibromo-9H-carbazole
benzyl alcohol
3,6-dibromo-9-benzyl-9H-carbazole
Conditions | Yield |
---|---|
With (trimethyl-λ5-phosphanyliden)acetonitrile In toluene at 110℃; for 15h; | 97% |
3,6-dibromo-9H-carbazole
4-methoxyphenylboronic acid
3,6-bis(4-methoxyphenyl)-9H-carbazole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 5h; Heating; | 97% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere; | 82% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 12h; Inert atmosphere; | 64% |
3,6-dibromo-9H-carbazole
ethyl bromoacetate
3,6-dibromo-carbazole-9-acetic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 2h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20 - 55℃; for 3h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 55℃; | 84% |
Stage #1: 3,6-dibromo-9H-carbazole With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 90℃; for 12h; | 84% |
zinc(II) cyanide
3,6-dibromo-9H-carbazole
9H-carbazole-3,6-dicarbonitrile
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; N,N-dimethyl-formamide for 0.75h; Inert atmosphere; Stage #2: zinc(II) cyanide With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; zinc diacetate; zinc In water; N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; | 97% |
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc(II) acetate dihydrate; zinc In water; N,N-dimethyl-formamide at 110 - 120℃; for 48h; Negishi Coupling; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With iron(III) trifluoromethanesulfonate; cyclomaltooctaose In 1,2-dichloro-ethane at 40℃; for 0.0833333h; Green chemistry; Stage #2: 1-ethenyl-4-methylbenzene In 1,2-dichloro-ethane at 40℃; Green chemistry; | 97% |
2-ethylhexyl bromide
3,6-dibromo-9H-carbazole
3,6-dibromo-9-(2-ethyl-hexyl)-9H-carbazole
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With potassium tert-butylate In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Stage #2: 3-bromomethylheptane In tetrahydrofuran Reflux; Inert atmosphere; Schlenk technique; | 96.2% |
With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 110℃; for 4h; | 80% |
Stage #1: 3,6-dibromo-9H-carbazole With tetrabutylammomium bromide; potassium hydroxide In toluene for 1h; Stage #2: 3-bromomethylheptane In toluene at 20℃; for 24h; Reflux; | 77% |
3,6-dibromo-9H-carbazole
1-(3',6'-dibromocarbazolyl)-2-propyne
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole; μ,η-hexacarbonyldicobaltopropynol With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Stage #2: With ferric nitrate In ethanol at 50℃; | 96% |
phenanthridine
3,6-dibromo-9H-carbazole
dimethyl acetylenedicarboxylate
C31H22Br2N2O4
Conditions | Yield |
---|---|
With water at 70℃; for 10h; | 96% |
3,6-dibromo-9H-carbazole
diphenylamine
N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 65℃; for 10h; Inert atmosphere; | 96% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 12h; Reflux; | 70% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; |
3,6-dibromo-9H-carbazole
1,2,4,5-tetrabromomethylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 20℃; | 95.9% |
3,6-dibromo-9H-carbazole
1-bromo-hexane
3,6-dibromo-9-hexyl-9H-carbazole
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium hydroxide In water at 20℃; for 0.5h; | 95% |
Stage #1: 3,6-dibromo-9H-carbazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 1-bromo-hexane In dimethyl sulfoxide at 20℃; for 10h; | 92.35% |
Stage #1: 3,6-dibromo-9H-carbazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 1-bromo-hexane In dimethyl sulfoxide at 20℃; | 92.35% |
3,6-dibromo-9H-carbazole
4-(diphenylamino)phenyl boronic acid
4,4'-(9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline)
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Inert atmosphere; Reflux; | 95% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water Suzuki Coupling; | 69% |
With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene for 4h; Reflux; | 68% |
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 3h; Suzuki-Miyaura Coupling; | 51% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene for 24h; Suzuki reaction; Reflux; |
phenanthridine
3,6-dibromo-9H-carbazole
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In dichloromethane at -10 - 20℃; | 95% |
3,6-dibromo-9H-carbazole
Di-tert-butyl acetylenedicarboxylate
triphenylphosphine
di-tert-buthyl 2-(3,6-dibromocarbazole-9-yl)-3-(triphenylphosphoranylidene)-butanedioate
Conditions | Yield |
---|---|
In acetone at 20℃; for 8h; Kinetics; Solvent; Temperature; Concentration; | 95% |
isoquinoline
3,6-dibromo-9H-carbazole
dimethyl acetylenedicarboxylate
C27H20Br2N2O4
Conditions | Yield |
---|---|
In dichloromethane at -10 - 20℃; | 95% |
1.Introduction of 3,6-Dibromocarbazole
The 3,6-Dibromo-9H-carbazole, with the CAS registry number 6825-20-3, is also known as Carbazole, 3,6-dibromo-. It belongs to the product categories of Carbazoles; Carbazoles (for Conduting Polymer Research); Functional Materials; Reagents for Conducting Polymer Research; Carbazole; Carbazoles Heterocyclic Building Blocks; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Apoptosis Inhibitors. This chemical's molecular formula is C12H7Br2N and molecular weight is 325.00. Its systematic name is called 3,6-dibromo-9H-carbazole. This chemical is tan to light green powder.
2.Physical properties of 3,6-Dibromo-9H-carbazole
(1)ACD/LogP: 5.26; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 1; (5)Index of Refraction: 1.796; (6)Molar Refractivity: 71.75 cm3; (7)Molar Volume: 168.3 cm3; (8)Surface Tension: 63.6 dyne/cm; (9)Density: 1.93 g/cm3; (10)Flash Point: 231.4 °C; (11)Enthalpy of Vaporization: 69.18 kJ/mol; (12)Boiling Point: 459 °C at 760 mmHg; (13)Vapour Pressure: 3.58E-08 mmHg at 25°C.
3.Structure descriptors of 3,6-Dibromocarbazole
(1)SMILES: Brc3cc2c1cc(Br)ccc1nc2cc3
(2)InChI: InChI=1/C12H7Br2N/c13-7-1-3-11-9(5-7)10-6-8(14)2-4-12(10)15-11/h1-6,15H
(3)InChIKey: FIHILUSWISKVSR-UHFFFAOYAI
4.Preparation of 3,6-Dibromocarbazole
The 3,6-Dibromocarbazole can be prepared by carbazole. This reaction will need reagent hydrochloric acid, glacial acetic acid, potassium bromide and potassium bromate.
5.Uses of 3,6-Dibromo-9H-carbazole
The 3,6-Dibromocarbazole can be used to produce 9-benzyl-3,6-dibromo-carbazole at temperature of 100 °C. This reaction will need reagent K2CO3 and solvent dimethylformamide with reaction time of 12 hours. The yield is about 81%.
6.Safety information of 3,6-Dibromocarbazole
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing and eye/face protection.
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