| Company Name: |
Alfa Aesar |
| Tel: |
400-6106006 |
| Email: |
saleschina@alfa-asia.com |
|
| | 2,5-Dibromonitrobenzene Basic information |
| | 2,5-Dibromonitrobenzene Chemical Properties |
| Melting point | 82-84 °C (lit.) | | Boiling point | 266.4°C (rough estimate) | | density | 2.374 g/mL at 25 °C (lit.) | | refractive index | 1.6400 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | form | Crystalline Powder | | color | Yellow | | Water Solubility | Slightly soluble in water. | | BRN | 1950425 | | InChI | InChI=1S/C6H3Br2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H | | InChIKey | WRGKKASJBOREMB-UHFFFAOYSA-N | | SMILES | C1(Br)=CC=C(Br)C=C1[N+]([O-])=O | | CAS DataBase Reference | 3460-18-2(CAS DataBase Reference) |
| Hazard Codes | Xn,N | | Risk Statements | 22-36/37/38-50-20/21/22 | | Safety Statements | 26-60-61-36/37/39-22 | | RIDADR | UN 3077 9 / PGIII | | WGK Germany | 2 | | HazardClass | 9 | | HS Code | 29049090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Acute 1
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2,5-Dibromonitrobenzene Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 2,5-Dibromonitrobenzene is a halogen-substituted nitrobenzenes used against Tetrahymena pyriformis due to its inhibitory and toxicity activities. | | Synthesis | The general procedure for the synthesis of 2,5-dibromonitrobenzene from 1,4-dibromobenzene was as follows: a mixture of nitric acid (90%, 4.6 g, 70 mmol) and concentrated sulfuric acid (75 mL) was slowly added dropwise to a solution of dichloromethane (30 mL) and concentrated sulfuric acid (20 mL) containing 1,4-dibromobenzene (11.8 g, 50 mmol), with the use of a dropping funnel during the addition. The acceleration of the drop was controlled and the reaction was carried out at room temperature for 20 min. After completion of the reaction, stirring of the reaction mixture was continued for 30 min. Subsequently, the reaction was quenched with 25% aqueous sodium hydroxide solution (3 mL), the reaction product was extracted with dichloromethane (30 mL) and the aqueous layer was washed with dichloromethane (10 mL). The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the light yellow crystalline product 2,5-dibromonitrobenzene (13.7 g, 97% yield) with a melting point of 83-84°C. The product was extracted by 1H NMR and the aqueous layer was washed with dichloromethane (10 mL). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3), δ 7.98 (d, J = 2.3 Hz, 1H), 7.55-7.63 (m, 2H). | | Purification Methods | It crystallises from Me2CO or EtOH. [Beilstein 5 H 250, 5 II 190, 5 III 621, 5 IV 732.] | | References | [1] Tetrahedron, 2004, vol. 60, # 1, p. 81 - 92
[2] European Journal of Organic Chemistry, 2012, # 36, p. 7066 - 7074
[3] Dyes and Pigments, 2013, vol. 96, # 3, p. 619 - 625
[4] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5448 - 5460
[5] Organic Letters, 2001, vol. 3, # 7, p. 993 - 995 |
| | 2,5-Dibromonitrobenzene Preparation Products And Raw materials |
|