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2-Bromocarbazole
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3652-90-2 Usage

Uses

Sensitive fluorogenic substrate for urokinase.

Chemical Properties

White solid
InChI:InChI=1/C12H8BrN/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7,14H

3652-90-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromocarbazole

1.2 Other means of identification

Product number -
Other names 2-Bromo-9H-carbazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3652-90-2 SDS

3652-90-2Synthetic route

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

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

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

4'-bromo-2-nitrobiphenyl

2-bromo-9H-carbazole
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

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

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

2-bromo-9H-carbazole
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

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

2-bromo-9H-carbazole
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

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

A

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

2-bromo-9H-carbazole

B

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

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

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

2-bromo-9H-carbazole
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%
4'-bromo-[1,1'-biphenyl]-2-amine
62532-98-3

4'-bromo-[1,1'-biphenyl]-2-amine

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

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

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

2-bromo-9H-carbazole

Conditions
ConditionsYield
With chloranil; xylene
4-Brom-2-azidobiphenyl
91330-90-4

4-Brom-2-azidobiphenyl

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

2-bromo-9H-carbazole

Conditions
ConditionsYield
With (thermal decomposition) In decalin at 148 - 163.6℃; Kinetics;
1,4-dibromo-2-nitrobenzene
3460-18-2

1,4-dibromo-2-nitrobenzene

phenylboronic acid
98-80-6

phenylboronic acid

A

2-bromo-9H-carbazole
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;
2-bromo-9H-carbazole
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
cyclohexanone
108-94-1

cyclohexanone

2-bromo-9H-carbazole
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
3-bromophenylhydrazine
40887-80-7

3-bromophenylhydrazine

2-bromo-9H-carbazole
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
2-hydroxycarbazole
86-79-3

2-hydroxycarbazole

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

2-bromo-9H-carbazole

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h;
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

2-bromo-9H-carbazole
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
1-iodo-4-bromo-2-nitrobenzene
112671-42-8

1-iodo-4-bromo-2-nitrobenzene

2-bromo-9H-carbazole
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
phenylboronic acid
98-80-6

phenylboronic acid

2-bromo-9H-carbazole
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
1,4-dibromo-2-nitrobenzene
3460-18-2

1,4-dibromo-2-nitrobenzene

2-bromo-9H-carbazole
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
4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

2-bromo-9H-carbazole
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
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-bromo-9H-carbazole
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
triethyl phosphate
78-40-0

triethyl phosphate

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

4'-bromo-2-nitrobiphenyl

A

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

2-bromo-9H-carbazole

B

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

2-bromo-9-ethyl-9H-carbazole

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

2-nitrophenyl bromide

2-bromo-9H-carbazole
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
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

2-bromoaniline
615-36-1

2-bromoaniline

2-bromo-9H-carbazole
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
1,4-dibromo-2-nitrobenzene
3460-18-2

1,4-dibromo-2-nitrobenzene

phenylboronic acid
98-80-6

phenylboronic acid

2-bromo-9H-carbazole
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
2-iodophenylamine
615-43-0

2-iodophenylamine

2-bromo-9H-carbazole
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

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

2-bromo-9H-carbazole
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
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

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

2-bromo-9H-carbazole

2-bromo-9-(tetrahydro-2H-pyran-2-yl)-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
2-bromo-pyridine
109-04-6

2-bromo-pyridine

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

2-bromo-9H-carbazole

2-bromo-9-(pyridin-2-yl)-9H-carbazole 3-Br
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

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

2-bromo-4-(tert-butyl)pyridine

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

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

2-bromo-9H-carbazole

diphenylamine
122-39-4

diphenylamine

N,N-diphenyl-(9H-carbazol-2-yl)amine
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%
2,5-dibromopyridine
624-28-2

2,5-dibromopyridine

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

2-bromo-9H-carbazole

2-bromo-9-(5-bromopyridin-2-yl)-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

phenylhydrazine
100-63-0

phenylhydrazine

9-(phenyl)-2-bromo-9H-carbazole
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-9H-carbazole
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

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

2-chloro-4,6-diphenylpyrimidine

C28H18BrN3

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

2-bromonicotinic acid methyl ester

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

2-bromo-9H-carbazole

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

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

2-bromo-9H-carbazole

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

2-bromo-4-(trifluoromethyl)pyridine

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

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

2-bromo-9H-carbazole

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

2-bromo-4-methoxypyridine

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

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

2-bromo-9H-carbazole

2-bromopyrimidine
4595-60-2

2-bromopyrimidine

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

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

2-Bromo-4-picoline

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

2-bromo-9H-carbazole

2-bromo-9-(4-methylpyridine-2-yl)-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

1,3-dihexyl-5-iodobenzene

1,3-dihexyl-5-iodobenzene

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

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

2-bromo-9H-carbazole

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

2-bromo-4-chloropyridine

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

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

2-bromo-9H-carbazole

2-bromo-3,6-diiodo-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

1-bromo-hexane
111-25-1

1-bromo-hexane

2-bromo-9-hexylcarbazole
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℃;
2-bromoquinoline
2005-43-8

2-bromoquinoline

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

2-bromo-9H-carbazole

2-bromo-9-(quinolin-2-yl)-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

1-bromo-octane
111-83-1

1-bromo-octane

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

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

2-bromo-9H-carbazole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 2-bromo-9H-carbazole-9-carboxylate
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

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

2-bromo-4-fluoro-pyridine

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

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%
2-bromopyrazine
56423-63-3

2-bromopyrazine

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

2-bromo-9H-carbazole

2-bromo-9-(pyrazin-2-yl)-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%
2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

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

2-bromo-9H-carbazole

2-bromo-9-(thiazol-2-yl)-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

iodobenzene
591-50-4

iodobenzene

9-(phenyl)-2-bromo-9H-carbazole
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1’:3' ,1

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

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%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

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

2-bromo-9H-carbazole

2-bromo-9-(5-methylpyridin-2-yl)-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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

methyl iodide
74-88-4

methyl iodide

2-bromo-9-methyl-9H-carbazole
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%
2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

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

biphenyl-4-yl-hydrazine

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