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3652-90-2

Basic Information
CAS No.: 3652-90-2
Name: 2-Bromo-9H-carbazole
Molecular Structure:
Molecular Structure of 3652-90-2 (2-Bromo-9H-carbazole)
Formula: C12H8BrN
Molecular Weight: 246.10
Synonyms: 9H-Carbazole, 2-bromo-;2-Bromocarbazole;
EINECS: 807-979-0
Density: 1.617 g/cm3
Melting Point: 253.0 to 257.0 °C
Boiling Point: 409.228 °C at 760 mmHg
Flash Point: 201.294 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 15.79000
LogP: 4.08360
Synthetic route

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

3652-90-2

2-bromo-9H-carbazole

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With chloranil; xylene
91330-90-4

4-Brom-2-azidobiphenyl

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
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
ConditionsYield
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;

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
for 5h; Inert atmosphere; Reflux;A 7.2 g
B 4.26 g
577-19-5

2-nitrophenyl bromide

3652-90-2

2-bromo-9H-carbazole

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