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6825-20-3

Basic Information
CAS No.: 6825-20-3
Name: 9H-Carbazole,3,6-dibromo-
Molecular Structure:
Molecular Structure of 6825-20-3 (9H-Carbazole,3,6-dibromo-)
Formula: C12H7Br2N
Molecular Weight: 325.00
Synonyms: Carbazole,3,6-dibromo- (6CI,7CI,8CI);3,6-Dibromo-9H-carbazole;NSC121206;3,6-Dibromocarbazole;
EINECS:
Density: 1.93 g/cm3
Melting Point: 204-206 °C(lit.)
Boiling Point: 459 °C at 760 mmHg
Flash Point: 231.4 °C
Solubility:
Appearance: tan to light green powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 15.79000
LogP: 4.84610
Synthetic route
86-74-8

9H-carbazole

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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%
86-74-8

9H-carbazole

A

1592-95-6

3-bromo-9H-carbazole

B

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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.
122-39-4

diphenylamine

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
With bromine In diethyl ether85%
With N-Bromosuccinimide In dichloromethane for 1h; Irradiation;84.6%
86-74-8

9H-carbazole

A

6825-20-3

3,6-dibromo-9H-carbazole

B

55119-10-3

1,3,6-tribromo-9H-carbazole

C

55119-09-0

1,3,6,8-tetrabromo-9-methyl-9H-carbazole

Conditions
ConditionsYield
With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 72h; Yield given. Yields of byproduct given;
5149-12-2

4,4'-dibromodiphenylnitrosamine

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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
16292-17-4

bis(4-bromophenyl)amine

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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
4051-56-3

N,N-diphenylbenzamide

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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
99234-92-1

N,N-bis-(4-bromophenyl)benzamide

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
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
5149-08-6

1,1-bis(4-bromophenyl)hydrazine

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / ethanol / 1 h / 70 °C
2: NaCl / acetonitrile / Photolysis
View Scheme

N-(4,4′-dibromodiphenylamino)-2,4,6-trimethylpyridinium tetrafluoroborate

A

4-bromo-N-(4-bromophenyl)-2-chloroaniline

B

6825-20-3

3,6-dibromo-9H-carbazole

C

16292-17-4

bis(4-bromophenyl)amine

Conditions
ConditionsYield
With sodium chloride In acetonitrile Photolysis;A 6.8 mg
B n/a
C n/a
912850-81-8

9-benzoyl-3,6-dibromo-carbazole

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
With potassium hydroxide
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

86-74-8

9H-carbazole

6825-20-3

3,6-dibromo-9H-carbazole

Conditions
ConditionsYield
With tetrachloromethane
7726-95-6

bromine

108-24-7

acetic anhydride

86-74-8

9H-carbazole

64-19-7

acetic acid

6825-20-3

3,6-dibromo-9H-carbazole

228091-77-8

N-nitroso-3,6-dibromocarbazole

67-64-1

acetone

6825-20-3

3,6-dibromo-9H-carbazole

7647-01-0

hydrogenchloride

228091-77-8

N-nitroso-3,6-dibromocarbazole

6825-20-3

3,6-dibromo-9H-carbazole

6825-20-3

3,6-dibromo-9H-carbazole

111-83-1

1-bromo-octane

79554-93-1

3,6-dibromo-9-octyl-9H-carbazole

Conditions
ConditionsYield
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%
6825-20-3

3,6-dibromo-9H-carbazole

350-46-9

4-Fluoronitrobenzene

255829-24-4

3,6-dibromo-9-(4-nitrophenyl)-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide100%
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%
6825-20-3

3,6-dibromo-9H-carbazole

115314-14-2, 115314-17-5

(R)-glycidyl nosylate

1260172-41-5

(-)-(S)-3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole

Conditions
ConditionsYield
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;
6825-20-3

3,6-dibromo-9H-carbazole

865-50-9

iodomethane-d3

C13H6(2)H3Br2N

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h;100%
6825-20-3

3,6-dibromo-9H-carbazole

544-92-3

copper(I) cyanide

57103-03-4

9H-carbazole-3,6-dicarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 70h; Heating;99%
109-65-9

1-bromo-butane

6825-20-3

3,6-dibromo-9H-carbazole

121602-03-7

3,6-dibromo-(N-n-butyl)carbazole

Conditions
ConditionsYield
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%
6825-20-3

3,6-dibromo-9H-carbazole

100-51-6

benzyl alcohol

118599-27-2

3,6-dibromo-9-benzyl-9H-carbazole

Conditions
ConditionsYield
With (trimethyl-λ5-phosphanyliden)acetonitrile In toluene at 110℃; for 15h;97%
6825-20-3

3,6-dibromo-9H-carbazole

5720-07-0

4-methoxyphenylboronic acid

399042-83-2

3,6-bis(4-methoxyphenyl)-9H-carbazole

Conditions
ConditionsYield
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%
6825-20-3

3,6-dibromo-9H-carbazole

105-36-2

ethyl bromoacetate

124985-06-4

3,6-dibromo-carbazole-9-acetic acid ethyl ester

Conditions
ConditionsYield
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%
557-21-1

zinc(II) cyanide

6825-20-3

3,6-dibromo-9H-carbazole

57103-03-4

9H-carbazole-3,6-dicarbonitrile

Conditions
ConditionsYield
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%
622-97-9

1-ethenyl-4-methylbenzene

6825-20-3

3,6-dibromo-9H-carbazole

C21H17Br2N

Conditions
ConditionsYield
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%
18908-66-2

2-ethylhexyl bromide

6825-20-3

3,6-dibromo-9H-carbazole

173063-52-0

3,6-dibromo-9-(2-ethyl-hexyl)-9H-carbazole

Conditions
ConditionsYield
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%
6825-20-3

3,6-dibromo-9H-carbazole

μ,η-hexacarbonyldicobaltopropynol

μ,η-hexacarbonyldicobaltopropynol

105729-54-2

1-(3',6'-dibromocarbazolyl)-2-propyne

Conditions
ConditionsYield
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%
229-87-8

phenanthridine

6825-20-3

3,6-dibromo-9H-carbazole

762-42-5

dimethyl acetylenedicarboxylate

1357456-46-2

C31H22Br2N2O4

Conditions
ConditionsYield
With water at 70℃; for 10h;96%
6825-20-3

3,6-dibromo-9H-carbazole

122-39-4

diphenylamine

608527-58-8

N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine

Conditions
ConditionsYield
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;
6825-20-3

3,6-dibromo-9H-carbazole

15442-91-8

1,2,4,5-tetrabromomethylbenzene

9,9',9'',9'''-[benzene-1,2,4,5-tetrayltetrakis(methylene)]tetrakis(3,6-dibromo-9H-carbazole)

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃;95.9%
6825-20-3

3,6-dibromo-9H-carbazole

111-25-1

1-bromo-hexane

150623-72-6

3,6-dibromo-9-hexyl-9H-carbazole

Conditions
ConditionsYield
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%
6825-20-3

3,6-dibromo-9H-carbazole

201802-67-7

4-(diphenylamino)phenyl boronic acid

885665-26-9

4,4'-(9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline)

Conditions
ConditionsYield
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;
229-87-8

phenanthridine

6825-20-3

3,6-dibromo-9H-carbazole

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(6-(3,6-diboromo-9H-carbazole-9-yl)phenanthridine-5(6H)-yl)fumarate

Conditions
ConditionsYield
In dichloromethane at -10 - 20℃;95%
6825-20-3

3,6-dibromo-9H-carbazole

66086-33-7

Di-tert-butyl acetylenedicarboxylate

603-35-0

triphenylphosphine

1190703-81-1

di-tert-buthyl 2-(3,6-dibromocarbazole-9-yl)-3-(triphenylphosphoranylidene)-butanedioate

Conditions
ConditionsYield
In acetone at 20℃; for 8h; Kinetics; Solvent; Temperature; Concentration;95%
119-65-3

isoquinoline

6825-20-3

3,6-dibromo-9H-carbazole

762-42-5

dimethyl acetylenedicarboxylate

1253914-46-3

C27H20Br2N2O4

Conditions
ConditionsYield
In dichloromethane at -10 - 20℃;95%
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    3,6-Dibromocarbazole

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Specification

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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