|
|
| | 1,3-DIBROMO-5-IODOBENZENE Basic information | | Uses |
| Product Name: | 1,3-DIBROMO-5-IODOBENZENE | | Synonyms: | Benzene,1,3-dibromo-5-iodo-;1,3-DIBROMO-5-IODOBENZENE 25G;1,3-DIBROMO-5-IODOBENZENE;3,5-DIBROMOIODOBENZENE;1-Iodo-3,5-dibromobenzene;3,5-Dibromophenyl iodide;1,3-Dibromo-5-iodobenzene>;1,3-DIBROMO-5-IODOBENZENE ISO 9001：2015 REACH | | CAS: | 19752-57-9 | | MF: | C6H3Br2I | | MW: | 361.8 | | EINECS: | | | Product Categories: | organic chemicals and derivatives/others;OLED | | Mol File: | 19752-57-9.mol |  |
| | 1,3-DIBROMO-5-IODOBENZENE Chemical Properties |
| Melting point | 124.4-124.7℃ | | Boiling point | 302.7±32.0 °C(Predicted) | | density | 2.514±0.06 g/cm3 (20 ºC 760 Torr) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | powder to crystal | | color | Light yellow to Brown | | InChI | InChI=1S/C6H3Br2I/c7-4-1-5(8)3-6(9)2-4/h1-3H | | InChIKey | KARUMYWDGQTPFL-UHFFFAOYSA-N | | SMILES | C1(Br)=CC(I)=CC(Br)=C1 |
| | 1,3-DIBROMO-5-IODOBENZENE Usage And Synthesis |
| Uses | 1,3-Dibromo-5-iodobenzene is an important organic intermediate widely used in the fields of dyes, pigments, pharmaceuticals and pesticides. | | Chemical Properties | Reddish brown powder | | Synthesis | The general procedure for the synthesis of 1,3-dibromo-5-iodobenzene from 2,6-dibromo-4-iodoaniline is as follows:
1. Preparation of 3,5-dibromoiodobenzene: 188.4 g of 2,6-dibromo-4-iodoaniline and 600 g of hypophosphorous acid were added to the reaction vessel at room temperature and stirred well. Subsequently, a solution formed by dissolving 34.5 g of sodium nitrite in 60 ml of water was added dropwise. The reaction is violently exothermic and the reaction temperature needs to be controlled at 20-25°C by means of a water bath. After the dropwise addition was completed, the reaction was continued for about 3 hours until a large white solid precipitate was observed. The reaction was continued at this temperature for 1 hour. The progress of the reaction was monitored by HPLC and stopped when the raw material 2,6-dibromo-4-iodoaniline completely disappeared. The crude product was collected by filtration.
2. Purification of the crude product: the crude product was dispersed in three 1000 ml flasks, 700 ml of anhydrous ethanol was added to each flask, and the product was heated to reflux (ca. 80 °C) to completely dissolve the product. Subsequently, it was cooled to 20-25 °C, the crystals were collected by filtration and dried under reduced pressure at 60 °C to obtain white needle-like crystals of 136 g. The purity of the product, 3,5-dibromo-2-iodobenzene, was 99.72% by HPLC analysis and the reaction yield was 75.2%. | | References | [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
[3] Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8661 - 8666
[4] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 882 - 896
[5] Patent: CN105523884, 2016, A. Location in patent: Paragraph 0014; 0016; 0017 |
| | 1,3-DIBROMO-5-IODOBENZENE Preparation Products And Raw materials |
| Raw materials | Benzenamine, 2,4-dibromo-6-iodo--->3-BROMO-5-IODOBENZOIC ACID-->2,6-Dibromo-4-nitroaniline-->2,6-dibromo-4-iodoaniline-->3,5-DIBROMO-1-TRIMETHYLSILYLBENZENE-->3,5-DIBROMOSULFANILIC ACID, SODIUM SALT-->3,5-DIBROMONITRO BENZENE-->3,5-Dibromoaniline-->1,3,5-Tribromobenzene-->4-Iodoaniline-->4-Nitroaniline |
|