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| Product Name: | 2,4,5-Tribromoimidazole | | Synonyms: | 1H-Imidazole, 2,4,5-tribromo-;2,4,5-tribromo-imidazol;TIMTEC-BB SBB001252;2,4,5-TRIBROMOIMIDAZOLE;2,4,5-tribromoimidazo;2,4,5-Tribromoimidazole,97%;2,4,5-TribroMoiMidazole, 97% 25GR;2,4,5-TribroMoiMidazole, 97% 5GR | | CAS: | 2034-22-2 | | MF: | C3HBr3N2 | | MW: | 304.77 | | EINECS: | 217-997-5 | | Product Categories: | alkyl bromide;Imidazol&Benzimidazole;Miscellaneous;Imidaxoles;Halogenated Heterocycles;Heterocyclic Building Blocks;ImidazolesBuilding Blocks;blocks;Bromides;Imidazoles | | Mol File: | 2034-22-2.mol |  |
| | 2,4,5-Tribromoimidazole Chemical Properties |
| Melting point | 217-220 °C (dec.) (lit.) | | Boiling point | 401.3±48.0 °C(Predicted) | | density | 3.8211 (rough estimate) | | refractive index | 1.6500 (estimate) | | storage temp. | 2-8°C | | form | Powder | | pka | 6.32±0.10(Predicted) | | color | Beige-yellow | | BRN | 115314 | | InChI | 1S/C3HBr3N2/c4-1-2(5)8-3(6)7-1/h(H,7,8) | | InChIKey | JCGGPCDDFXIVQB-UHFFFAOYSA-N | | SMILES | Brc1nc(Br)c(Br)[nH]1 | | CAS DataBase Reference | 2034-22-2(CAS DataBase Reference) | | NIST Chemistry Reference | Imidazole, 2,4,5-tribromo-(2034-22-2) |
| Hazard Codes | T,Xi | | Risk Statements | 23/24/25-36/37/38-25 | | Safety Statements | 22-26-36/37/39-45 | | RIDADR | UN 2811 6.1/PG 2 | | WGK Germany | 3 | | RTECS | NI8660000 | | Hazard Note | Irritant | | HazardClass | 6.1 | | PackingGroup | II | | HS Code | 29332990 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 2 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2,4,5-Tribromoimidazole Usage And Synthesis |
| Application | 2,4,5-Tribromoimidazole is an organic intermediate that can be obtained by brominating imidazole. 2,4,5-Tribromoimidazole can be debrominated to give 4,5-dibromoimidazole. | | Chemical Properties | BEIGE-YELLOW POWDER | | Uses | 2,4,5-Tribromoimidazole(2,4,5-TBI) on condensation with sugar precursors yields 2,4,5-TBI nucleosides. | | General Description | 2,4,5-Tribromoimidazole(2,4,5-TBI) on condensation with sugar precursors yields 2,4,5-TBI nucleosides. | | Biochem/physiol Actions | 2,4,5-Tribromoimidazole induces poisoning typical of uncouplers of oxidative phosphorylation in rats. | | Synthesis | The general procedure for the synthesis of 2,4,5-tribromoimidazole from imidazole was as follows: to a three-necked flask equipped with a thermostatic separatory funnel was added imidazole (29.24 g, 0.43 mol), sodium acetate (317.34 g, 3.87 mol) and acetic acid (150 mL). The mixture was dissolved in additional acetic acid (100 mL). Bromine (65 mL, 1.28 mol) was added slowly dropwise through a thermostatic separatory funnel at room temperature, controlling the reaction temperature to not exceed 40°C. After the dropwise addition was completed, the reaction mixture continued to be stirred for 3 hours at room temperature. Upon completion of the reaction, the reaction solution was poured into 1.5 L of water to induce precipitation of the solid product. The solid product was collected by filtration and washed several times with water to remove impurities. Finally, the solid product was dried to afford the target compound 2,4,5-tribromoimidazole (120 g, 92% yield). | | References | [1] Patent: CN106256830, 2016, A. Location in patent: Paragraph 0044; 0049; 0050; 0051
[2] Tetrahedron Letters, 2015, vol. 56, # 41, p. 5646 - 5650
[3] Tetrahedron Letters, 1998, vol. 39, # 44, p. 8163 - 8166
[4] Tetrahedron, 1999, vol. 55, # 4, p. 935 - 942
[5] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2740 - 2741 |
| | 2,4,5-Tribromoimidazole Preparation Products And Raw materials |
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