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| | 4-Bromo-1,2-benzenediamine Basic information |
| | 4-Bromo-1,2-benzenediamine Chemical Properties |
| Melting point | 65-69 °C (dec.)(lit.) | | Boiling point | 289.3±20.0 °C(Predicted) | | density | 1.697±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in chloroform. | | pka | 3.46±0.10(Predicted) | | form | powder to crystal | | color | White to Brown | | InChI | InChI=1S/C6H7BrN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2 | | InChIKey | WIHHVKUARKTSBU-UHFFFAOYSA-N | | SMILES | C1(N)=CC=C(Br)C=C1N | | CAS DataBase Reference | 1575-37-7(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 25-36/38-43 | | Safety Statements | 26-36/37-45 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | Hazard Note | Toxic | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29215110 |
| | 4-Bromo-1,2-benzenediamine Usage And Synthesis |
| Chemical Properties | White solid | | Uses | 4-Bromo-1,2-diaminobenzene can be used as a precursor for preparing fluorescent dipolar quinoxaline derivatives, which can find applications as potential emissive and electron-transport materials. It can also be used in the synthesis of 6-bromo-2-methylbenzimidazole. | | Uses | 4-Bromo-o-phenylenediamine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. | | General Description | 4-Bromo-1,2-diaminobenzene can be obtained from 1,2-diaminobenzene via acetylation followed by bromination and alkaline hydrolysis. | | Synthesis | 1. 4-Bromo-2-nitroaniline (600 mg, 2.76 mmol) was dissolved in 25 mL of anhydrous ethanol.
2. Stannous chloride (SnCl2, 2.72 g, 14 mmol) was added to the solution.
3. The reaction mixture was heated to reflux overnight. 4.
4. After completion of the reaction, the ethanol was removed by rotary evaporator under reduced pressure.
5. The residue was alkalized to pH 11 with 2 N sodium hydroxide solution.
6. The organic layer was collected by extraction with ether.
7. The organic layer was dried with anhydrous sodium sulfate.
8. After filtration, the organic layer was concentrated by rotary evaporator under reduced pressure to give the crude product 4-bromophthalimide (486 mg, 2.6 mmol, 94% yield).
9. The crude product was used directly in the next reaction without further purification. | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 827 - 832
[2] Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2317 - 2325
[3] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 11, p. 2591 - 2600
[4] Patent: US6063801, 2000, A
[5] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3186 - 3193 |
| | 4-Bromo-1,2-benzenediamine Preparation Products And Raw materials |
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