2-Bromocarbazole supplier | CasNO.3652-90-2

Name
2-BROMOCARBAZOLE
EINECS 807-979-0
CAS No. 3652-90-2
Article Data64
CAS DataBase
Density 1.617 g/cm³
Solubility
Melting Point 253.0 to 257.0 °C
Formula C₁₂H₈BrN
Boiling Point 409.228 °C at 760 mmHg
Molecular Weight 246.106
Flash Point 201.294 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 9H-Carbazole, 2-bromo-;2-Bromocarbazole;
PSA 15.79000
LogP 4.08360

Synthetic route

: 2-bromo-9-(pyrimidin-2-yl)-9H-carbazole

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water; copper(l) chloride; sodium t-butanolate In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere;	99%

: 35450-34-1
4'-bromo-2-nitrobiphenyl

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With triphenylphosphine In 1,2-dichloro-benzene at 170℃; for 12h; Inert atmosphere;	89%
With triethyl phosphite In 1,2-dichloro-benzene at 80 - 150℃; Inert atmosphere;	75%
Stage #1: 4'-bromo-2-nitrobiphenyl With triethyl phosphite at 160℃; for 2h; Stage #2: With hydrogenchloride In water for 1h; Reflux;	67.6%

2-bromo-9H-carbazole: 2-bromo-9H-carbazole

Conditions

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;	83%

Conditions

Conditions	Yield
With triethylphosphine for 12h; Reflux;	82.4%
With triphenylphosphine In 1,2-dichloro-benzene at 200℃;	77%
With triphenylphosphine In 1,2-dichloro-benzene Inert atmosphere; Reflux;	77%

1-bromo-3-nitrosobenzene: 1-bromo-3-nitrosobenzene

: 88284-48-4
2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; regioselective reaction;	80%

: 2-azido-4'-bromo-1,1'-biphenyl

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
In tetrahydrofuran for 4h; Solvent; Inert atmosphere; Irradiation;	80%

: 2-bromo-9-(pyrimidin-2-yl)-9H-carbazole

A: 3652-90-2
2-bromo-9H-carbazole

B: 2-hydroxy-9-(2-pyrimidinyl)carbazole

Conditions

Conditions	Yield
With N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water; copper(l) chloride; sodium hydroxide In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere;	A 74% B 26%

: 3-bromodibenzo[b,d]iodol-5-ium trifluoromethanesulfonate

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With sodium azide; copper(I) thiophene-2-carboxylate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere; Schlenk technique;	63%
With sodium azide; copper(I) thiophene-2-carboxylate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere; Schlenk technique;	63%

: 62532-98-3
4'-bromo-[1,1'-biphenyl]-2-amine

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate; Trimethylacetic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 12h;	33%
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite / water / 1 h / 0 °C 1.2: Sandmeyer Reaction / 1 h / 0 - 20 °C / Inert atmosphere 2.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water; tetrahydrofuran / 1 h / 0 - 5 °C 1.2: 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C 3.1: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; sodium hydrogencarbonate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique View Scheme

: 78863-99-7
7-bromo-2,3,4,9-tetrahydro-1H-carbazole

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With chloranil; xylene

: 91330-90-4
4-Brom-2-azidobiphenyl

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With (thermal decomposition) In decalin at 148 - 163.6℃; Kinetics;

: 3460-18-2
1,4-dibromo-2-nitrobenzene

: 98-80-6
phenylboronic acid

A: 3652-90-2
2-bromo-9H-carbazole

B

Conditions

Conditions	Yield
Stage #1: 1,4-dibromo-2-nitrobenzene; phenylboronic acid With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 90℃; for 5.5h; Suzuki-Miyaura coupling; Stage #2: With triethyl phosphite for 10h; Heating; Title compound not separated from byproducts;

...Expand

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 37 percent / Br2; FeCl3 / CH2Cl2 / Heating 2: 39 percent / triethyl phosphite / 12 h / Heating View Scheme
Multi-step reaction with 2 steps 1: iron(III) chloride; bromine / water 2: triethyl phosphite / 160 °C View Scheme
Multi-step reaction with 2 steps 1.1: iron(III) chloride / water / 0.5 h / 60 °C / Inert atmosphere 1.2: Reflux 2.1: triethyl phosphite / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: iron(III) chloride; bromine / tetrachloromethane / 12 h / 0 - 20 °C 2: triethyl phosphate / 7 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: iron(III) chloride / water / 4 h / Inert atmosphere; Reflux 2: triethyl phosphite / Inert atmosphere; Reflux View Scheme

: 108-94-1
cyclohexanone

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: tetrachloro-<1,4>benzoquinone; xylene View Scheme

: 40887-80-7
3-bromophenylhydrazine

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: tetrachloro-<1,4>benzoquinone; xylene View Scheme

: 86-79-3
2-hydroxycarbazole

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h;

: 5467-74-3
4-Bromophenylboronic acid

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
With potassium carbonate; Pd(PPh3)4 In 1,2-dimethoxyethane; hexane; water; ethyl acetate
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2: triethyl phosphite / 6 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine)palladium (0) / water; ethyl acetate; 1,2-dimethoxyethane 2: nitrogen; triphenylphosphine / ethyl acetate; 1,2-dichloro-benzene; methanol View Scheme

: 112671-42-8
1-iodo-4-bromo-2-nitrobenzene

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; potassium carbonate; triphenylphosphine / water; toluene / 8 h / 70 °C 2: triethyl phosphite / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C View Scheme

: 98-80-6
phenylboronic acid

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; potassium carbonate; triphenylphosphine / water; toluene / 8 h / 70 °C 2: triethyl phosphite / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 6 h / 90 °C 2: triethyl phosphite / 18 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 8 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere View Scheme

: 3460-18-2
1,4-dibromo-2-nitrobenzene

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 6 h / 90 °C 2: triethyl phosphite / 18 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 8 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / 5.5 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 10 h / Reflux; Inert atmosphere View Scheme

: 92-66-0
4-bromo-1,1'-biphenyl

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; acetic acid / 5 h / Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 180 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid; acetic acid / water 2: triethyl phosphite / 24 h / Reflux View Scheme

: 609-73-4
o-nitroiodobenzene

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2: triethyl phosphite / 6 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine)palladium (0) / water; ethyl acetate; 1,2-dimethoxyethane 2: nitrogen; triphenylphosphine / ethyl acetate; 1,2-dichloro-benzene; methanol View Scheme
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 16 h / Inert atmosphere; Reflux 2.1: triethyl phosphite / Inert atmosphere; Reflux 2.2: 3 h / 80 °C View Scheme

: 78-40-0
triethyl phosphate

: 35450-34-1
4'-bromo-2-nitrobiphenyl

A: 3652-90-2
2-bromo-9H-carbazole

B: 56166-63-3
2-bromo-9-ethyl-9H-carbazole

Conditions

Conditions	Yield
for 5h; Inert atmosphere; Reflux;	A 7.2 g B 4.26 g

...Expand

: 577-19-5
2-nitrophenyl bromide

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene / 5 h / Reflux 2: iron(III) chloride; bromine / tetrachloromethane / 12 h / 0 - 20 °C 3: triethyl phosphate / 7 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 90 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 170 °C / Inert atmosphere View Scheme

: 5467-74-3
4-Bromophenylboronic acid

: 615-36-1
2-bromoaniline

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 24 h / 80 °C / Inert atmosphere 2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Trimethylacetic acid; copper diacetate / 1-methyl-pyrrolidin-2-one / 12 h / 120 °C View Scheme

: 3460-18-2
1,4-dibromo-2-nitrobenzene

: 98-80-6
phenylboronic acid

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 8 h / Reflux; Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 8 h / 180 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; 1,4-dioxane / 12 h / Reflux 2: triethylphosphine / 12 h / Reflux View Scheme

: 615-43-0
2-iodophenylamine

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere; Sealed tube 2.1: acetic acid; sodium nitrite / water / 1 h / 0 °C 2.2: Sandmeyer Reaction / 1 h / 0 - 20 °C / Inert atmosphere 3.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation View Scheme
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C 2.1: hydrogenchloride; sodium nitrite / water; tetrahydrofuran / 1 h / 0 - 5 °C 2.2: 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C 4.1: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; sodium hydrogencarbonate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique View Scheme

Yield

Multi-step reaction with 3 steps
1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere; Sealed tube
2.1: acetic acid; sodium nitrite / water / 1 h / 0 °C
2.2: Sandmeyer Reaction / 1 h / 0 - 20 °C / Inert atmosphere
3.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation
View Scheme

Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C
2.1: hydrogenchloride; sodium nitrite / water; tetrahydrofuran / 1 h / 0 - 5 °C
2.2: 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C
4.1: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; sodium hydrogencarbonate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique
View Scheme

: 4'-bromo-2-iodo-1,1'-biphenyl

: 3652-90-2
2-bromo-9H-carbazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C 2: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; sodium hydrogencarbonate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique View Scheme

: 110-87-2
3,4-dihydro-2H-pyran

: 3652-90-2
2-bromo-9H-carbazole

: 183012-41-1
2-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane Reflux;	99%
pyridinium p-toluenesulfonate In dichloromethane at 20 - 50℃; for 4h;	90%
With camphor-10-sulfonic acid In dichloromethane

: 109-04-6
2-bromo-pyridine

: 3652-90-2
2-bromo-9H-carbazole

: 1352932-32-1
2-bromo-9-(pyridin-2-yl)-9H-carbazole 3-Br

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 24h; Concentration; Reagent/catalyst; Inert atmosphere;	99%
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; Inert atmosphere;	99%
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 144h; Glovebox; Sealed tube;	99%

: 3652-90-2
2-bromo-9H-carbazole

: 50488-34-1
2-bromo-4-(tert-butyl)pyridine

: 2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 24h; Inert atmosphere;	99%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 24h; Inert atmosphere;	99%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 20 - 130℃; for 48h; Inert atmosphere;	99%
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 115 - 125℃; for 96h; Inert atmosphere;	96%
With copper(l) iodide; potassium carbonate In toluene at 115 - 125℃; for 96h; Inert atmosphere;	96%

: 3652-90-2
2-bromo-9H-carbazole

: 122-39-4
diphenylamine

: 929099-71-8
N,N-diphenyl-(9H-carbazol-2-yl)amine

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere;	99%

: 624-28-2
2,5-dibromopyridine

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-9-(5-bromopyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 5h; Inert atmosphere;	98%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 5h; Ullmann Condensation; chemoselective reaction;	80%

: 3652-90-2
2-bromo-9H-carbazole

: 100-63-0
phenylhydrazine

: 94994-62-4
9-(phenyl)-2-bromo-9H-carbazole

Conditions

Conditions	Yield
With cobalt(II) phthalocyanine; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 60℃; for 12h; Schlenk technique;	98%

: 3652-90-2
2-bromo-9H-carbazole

: 98-80-6
phenylboronic acid

: 88590-00-5
2-phenyl-9H-carbazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 120℃; for 5h;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 5h; Reflux;	86%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 5h; Reflux;	86%

: 3652-90-2
2-bromo-9H-carbazole

: 2915-16-4
2-chloro-4,6-diphenylpyrimidine

: C28H18BrN3

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 70℃; for 16.5h; Inert atmosphere;	97%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Inert atmosphere;	90%

: 52718-95-3
2-bromonicotinic acid methyl ester

: 3652-90-2
2-bromo-9H-carbazole

: methyl 2-(2-bromo-9H-carbazol-9-yl)pyridine-3-carboxylate

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; L-proline In toluene at 105 - 115℃; for 24h; Inert atmosphere;	97%
With copper(l) iodide; potassium carbonate; L-proline In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;

: 3652-90-2
2-bromo-9H-carbazole

: 175205-81-9
2-bromo-4-(trifluoromethyl)pyridine

: 2-bromo-9-(4-(trifluoromethyl)pyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 24h; Inert atmosphere;	97%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 12h; Schlenk technique; Inert atmosphere;	88%

: 3652-90-2
2-bromo-9H-carbazole

: 89488-29-9
2-bromo-4-methoxypyridine

: 2-bromo-9-(4-methoxypyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 15h; Ullmann Condensation; Inert atmosphere;	97%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide for 15h;	95%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 120℃; for 15h; Inert atmosphere;	95%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 12h; Schlenk technique; Inert atmosphere;	94%

: 3652-90-2
2-bromo-9H-carbazole

: 4595-60-2
2-bromopyrimidine

: 2-bromo-9-(pyrimidin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 7h; Inert atmosphere;	96%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 7h; Ullmann Condensation; chemoselective reaction;	96%

: 4926-28-7
2-Bromo-4-picoline

: 3652-90-2
2-bromo-9H-carbazole

: 1404169-08-9
2-bromo-9-(4-methylpyridine-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Inert atmosphere;	95%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Ullmann Condensation; chemoselective reaction;	95%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 20 - 130℃; for 48h; Inert atmosphere;	95%

: 3652-90-2
2-bromo-9H-carbazole

: 1,3-dihexyl-5-iodobenzene

: 2-bromo-9-(3,5-dihexylphenyl)-9H-carbazole

Conditions

Conditions	Yield
With 1,10-Phenanthroline; copper(l) chloride; potassium hydroxide In o-xylene at 100 - 140℃; for 21h; Inert atmosphere;	95%

: 3652-90-2
2-bromo-9H-carbazole

: 22918-01-0
2-bromo-4-chloropyridine

: 2-bromo-9-(4-chloropyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 24h; Inert atmosphere;	95%

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-3,6-diiodo-9H-carbazole

Conditions

Conditions	Yield
With diphenyliodonium tetrafluoroborate; copper(II) sulfate In acetonitrile for 0.666667h; Inert atmosphere; Reflux;	95%

: 3652-90-2
2-bromo-9H-carbazole

: 111-25-1
1-bromo-hexane

: 864550-95-8
2-bromo-9-hexylcarbazole

Conditions

Conditions	Yield
Stage #1: 2-bromo-9H-carbazole With tetrabutylammomium bromide; sodium hydroxide at 20℃; for 0.0833333h; Stage #2: 1-bromo-hexane for 12h;	94%
Stage #1: 2-bromo-9H-carbazole With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 130℃;

: 2005-43-8
2-bromoquinoline

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-9-(quinolin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 3h; Inert atmosphere;	94%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 3h; Ullmann Condensation; chemoselective reaction;	94%

: 3652-90-2
2-bromo-9H-carbazole

: 111-83-1
1-bromo-octane

: 2-bromo-9-n-octyl-9H-carbazole

Conditions

Conditions	Yield
Stage #1: 2-bromo-9H-carbazole With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; Stage #2: 1-bromo-octane In dimethyl sulfoxide at 20℃; for 8h;	93%
In toluene at 80℃; for 16h; Inert atmosphere; Alkaline conditions;	68.6%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dimethyl sulfoxide for 8.5h;	65%

: 3652-90-2
2-bromo-9H-carbazole

: 24424-99-5
di-tert-butyl dicarbonate

: 1247868-53-6
tert-butyl 2-bromo-9H-carbazole-9-carboxylate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	93%
With dmap In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	84%

: 3652-90-2
2-bromo-9H-carbazole

: 357927-50-5
2-bromo-4-fluoro-pyridine

: 2-bromo-9-(4-fluoropyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 4h; Inert atmosphere;	93%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 4h; Ullmann Condensation; chemoselective reaction;	93%

: 56423-63-3
2-bromopyrazine

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-9-(pyrazin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 7h; Inert atmosphere;	93%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 7h; Ullmann Condensation; chemoselective reaction;	93%

: 3034-53-5
2-bromo-1,3-thiazole

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-9-(thiazol-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 11h; Ullmann Condensation; chemoselective reaction;	93%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 130℃; for 8h; Inert atmosphere;	92%

: 3652-90-2
2-bromo-9H-carbazole

: 591-50-4
iodobenzene

: 94994-62-4
9-(phenyl)-2-bromo-9H-carbazole

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate; ethylenediamine In toluene for 12h; Reflux;	92.4%
With potassium phosphate; ethylenediamine for 12h; Reflux;	91.65%
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In para-xylene at 140℃; for 48h; Ullmann condensation; Inert atmosphere;	90%

: 3652-90-2
2-bromo-9H-carbazole

: 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1’:3' ,1"-terphenyl]-4-yl)-1,3,2-dioxaborolane

: 2-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux;	60%

: 3510-66-5
2-Bromo-5-methylpyridine

: 3652-90-2
2-bromo-9H-carbazole

: 2-bromo-9-(5-methylpyridin-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 3h; Inert atmosphere;	92%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2h; Ullmann Condensation; chemoselective reaction;	92%

: 3652-90-2
2-bromo-9H-carbazole

: 73183-34-3
bis(pinacol)diborane

: 1242412-60-7
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 85℃; for 4h; Sealed tube; Inert atmosphere;	92%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 130℃; for 3h;	38%

: 3652-90-2
2-bromo-9H-carbazole

: 74-88-4
methyl iodide

: 108793-89-1
2-bromo-9-methyl-9H-carbazole

Conditions

Conditions	Yield
Stage #1: 2-bromo-9H-carbazole With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	92%
Stage #1: 2-bromo-9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	72%

: 3652-90-2
2-bromo-9H-carbazole

: 2217-77-8
biphenyl-4-yl-hydrazine

: 1393835-87-4
9-[1,1’-biphenyl]-4-yl-2-bromo-9H-carbazole

Conditions

Conditions	Yield
With potassium carbonate; copper(II) nitrate In acetonitrile at 0℃; for 4h;	92%

2-Bromocarbazole Specification

1.Introduction of 2-Bromocarbazole

The 2-Bromocarbazole with the CAS number 3652-90-2 is also called 9H-Carbazole, 2-bromo-. The systematic name is 2-bromo-9H-carbazole. Its molecular formula is C₁₂H₈BrN. This chemical is a kind of organics. It should be stored in dry and cool environment.

2.The properties of the 2-Bromocarbazole

(1)ACD/LogP: 4.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 1527; (6)ACD/BCF (pH 7.4): 1527; (7)ACD/KOC (pH 5.5): 6614; (8)ACD/KOC (pH 7.4): 6614; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 15.79 Å²; (13)Index of Refraction: 1.784; (14)Molar Refractivity: 64.061 cm³; (15)Molar Volume: 152.172 cm³; (16)Polarizability: 25.396×10^-24cm³; (17)Surface Tension: 60.866 dyne/cm; (18)Enthalpy of Vaporization: 63.566 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

3.Structure descriptors of 2-Bromocarbazole

(1)SMILES: Brc1ccc2c3ccccc3nc2c1
(2)InChI: InChI=1/C12H8BrN/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7,14H
(3)InChIKey: PJRGCJBBXGNEGD-UHFFFAOYAK

Product Name

2-BROMOCARBAZOLE

Synthetic route

2-Bromocarbazole Specification

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