| Company Name: |
INTATRADE GmbH |
| Tel: |
+49 3493/605464 |
| Email: |
sales@intatrade.de |
| Company Name: |
Alfa Aesar |
| Tel: |
400-6106006 |
| Email: |
saleschina@alfa-asia.com |
|
| | 2-Bromo-2'-nitroacetophenone Basic information |
| Product Name: | 2-Bromo-2'-nitroacetophenone | | Synonyms: | 1-(2-Nitrophenyl)-2-bromoethanone;2'-Nitro-α-bromoacetophenone;2'-NITROPHENACYL BROMIDE;-Bromo-2'-Nitroacetophenone;-nitroacetophenone 99+% (GC);2-Bromo-2'-nitroacetophenone,98%;2-Bromo-2'-nitroacetophenone2'-Nitrophenacyl bromide;2-NITROPHENCYL BROMIDE | | CAS: | 6851-99-6 | | MF: | C8H6BrNO3 | | MW: | 244.04 | | EINECS: | | | Product Categories: | Ketone;Carbonyl Compounds;Halides | | Mol File: | 6851-99-6.mol |  |
| | 2-Bromo-2'-nitroacetophenone Chemical Properties |
| Melting point | 55-57 °C(lit.) | | Boiling point | 335.7±17.0 °C(Predicted) | | density | 1.671±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform, Methanol | | form | Crystalline Powder | | color | White to pale yellow | | λmax | 262nm(EtOH)(lit.) | | InChI | 1S/C8H6BrNO3/c9-5-8(11)6-3-1-2-4-7(6)10(12)13/h1-4H,5H2 | | InChIKey | SGXUUCSRVVSMGK-UHFFFAOYSA-N | | SMILES | [O-][N+](=O)c1ccccc1C(=O)CBr | | CAS DataBase Reference | 6851-99-6(CAS DataBase Reference) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-27-28-36/37/39-45 | | RIDADR | UN 3261 8/PG 2 | | WGK Germany | 3 | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29147000 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
| | 2-Bromo-2'-nitroacetophenone Usage And Synthesis |
| Chemical Properties | White to pale yellow crystalline powder | | Uses | 2-Bromo-2'-nitroacetophenone is used in the novel synthesis of 5-pyridylindolizine derivatives. | | Uses | 2-Bromo-2′-nitroacetophenone, an electroactive derivative-forming reagent, was used as a precolumn reagent for preparing prostaglandin derivatives. | | Synthesis Reference(s) | Canadian Journal of Chemistry, 61, p. 400, 1983 DOI: 10.1139/v83-072
The Journal of Organic Chemistry, 49, p. 438, 1984 DOI: 10.1021/jo00177a010 | | Synthesis | Under argon protection, 2'-nitroacetophenone (20 g, 121 mmol) and anhydrous aluminum trichloride (500 mg, 3.75 mmol) were dissolved in anhydrous ether (600 mL), stirred and cooled to 0 °C. Bromine (6.2 mL, 121 mmol) was added slowly dropwise for a controlled time of 1 hour. After the dropwise addition was completed, the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 3 hours (the reaction progress was monitored by TLC). After completion of the reaction, the organic layer was washed with water (3 x 200 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/petroleum ether, 70:30) to give 31.7 g of yellow solid 2-bromo-1-(2-nitrophenyl)ethanone. The product was recrystallized with methanol to give 26.1 g of pure product in 88% yield. The product was colorless micro-needle-like crystals; TLC Rf value (dichloromethane/petroleum ether, 70:30) was 0.4; 1H NMR (400 MHz, CDCl3) δ: 8.21 (dd, J=8.1, 1.2 Hz, 1H, Ar-H), 7.79 (td, J=7.5, 1.3 Hz, 1H, Ar-H), 7.68 (ddd, J= 8.1, 7.5, 1.6 Hz, 1H, Ar-H), 7.50 (dd, J=7.5, 1.6 Hz, 1H, Ar-H), 4.30 (s, 2H, CH2); 13C NMR (100 MHz, CDCl3) δ: 194.3 (C=O), 145.4 (Ar-C), 134.9 (Ar-C), 134.8 ( Ar-CH), 131.3 (Ar-CH), 129.1 (Ar-CH), 124.5 (Ar-CH), 33.9 (CH2). | | References | [1] Journal of Organic Chemistry, 1984, vol. 49, # 3, p. 438 - 442
[2] Arkivoc, 2014, vol. 2014, # 3, p. 256 - 273
[3] Patent: US4812470, 1989, A
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 35, p. 7865 - 7877
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2152 - 2156 |
| | 2-Bromo-2'-nitroacetophenone Preparation Products And Raw materials |
|