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| CAS No.: | 6825-20-3 |
|---|---|
| Name: | 9H-Carbazole,3,6-dibromo- |
| Article Data: | 114 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C12H7Br2N |
| Molecular Weight: | 325.002 |
| Synonyms: | Carbazole,3,6-dibromo- (6CI,7CI,8CI);3,6-Dibromo-9H-carbazole;NSC121206;3,6-Dibromocarbazole; |
| EINECS: | N/A |
| Density: | 1.93 g/cm3 |
| Melting Point: | 204-206 °C(lit.) |
| Boiling Point: | 459 °C at 760 mmHg |
| Flash Point: | 231.4 °C |
| Solubility: | N/A |
| Appearance: | tan to light green powder |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-37/39 |
| Transport Information: | N/A |
| PSA: | 15.79000 |
| LogP: | 4.84610 |
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide In tetrahydrofuran at 85℃; for 48h; | 98% |
| With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at 20℃; | 97% |
| With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In ethanol at 20 - 25℃; for 2h; | 96% |
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 24h; | A 47% B n/a |
| With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 0.33h; Product distribution; one to four equivalents of NBS, other times; other N-heterocycles; | |
| With tetra-N-butylammonium tribromide In chloroform for 0.5h; Product distribution; Ambient temperature; other reaction times, different substrate/reagent ratios; | A 62 % Chromat. B 17 % Chromat. |
| Conditions | Yield |
|---|---|
| With bromine In diethyl ether | 85% |
| With N-Bromosuccinimide In dichloromethane for 1h; Irradiation; | 84.6% |
9H-carbazole
A
3,6-dibromo-9H-carbazole
B
1,3,6-tribromo-9H-carbazole
C
1,3,6,8-tetrabromo-9-methyl-9H-carbazole
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 72h; Yield given. Yields of byproduct given; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 2: 81 percent / ethanol / 1 h / 70 °C 3: NaCl / acetonitrile / Photolysis View Scheme |
bis(4-bromophenyl)amine
3,6-dibromo-9H-carbazole
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 2: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 3: 81 percent / ethanol / 1 h / 70 °C 4: NaCl / acetonitrile / Photolysis View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: Br2 / CH2Cl2 / 8 h / Heating 2: 23.44 g / KOH / ethanol; H2O / 1.5 h / Heating 3: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 4: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 5: 81 percent / ethanol / 1 h / 70 °C 6: NaCl / acetonitrile / Photolysis View Scheme |
N,N-bis-(4-bromophenyl)benzamide
3,6-dibromo-9H-carbazole
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: 23.44 g / KOH / ethanol; H2O / 1.5 h / Heating 2: 9.0 g / NaNO2; HCl / H2O; ethanol / 0.92 h 3: 58 percent / acetic acid; zinc; HCl / tetrahydrofuran; ethanol; H2O / 0.5 h 4: 81 percent / ethanol / 1 h / 70 °C 5: NaCl / acetonitrile / Photolysis View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 81 percent / ethanol / 1 h / 70 °C 2: NaCl / acetonitrile / Photolysis View Scheme |
B
3,6-dibromo-9H-carbazole
C
bis(4-bromophenyl)amine
| Conditions | Yield |
|---|---|
| With sodium chloride In acetonitrile Photolysis; | A 6.8 mg B n/a C n/a |
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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.
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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%.
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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.
