| Company Name: |
Alfa Aesar |
| Tel: |
400-6106006 |
| Email: |
saleschina@alfa-asia.com |
|
| | 3-Nitrophenacylbromide Basic information |
| | 3-Nitrophenacylbromide Chemical Properties |
| Melting point | 90-96 °C(lit.) | | Boiling point | 288.6±15.0 °C(Predicted) | | density | 1.8033 (rough estimate) | | refractive index | 1.6090 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Soluble in methanol. | | form | Crystalline Powder | | color | Beige-orange to yellow-green | | BRN | 610594 | | InChI | 1S/C8H6BrNO3/c9-5-8(11)6-2-1-3-7(4-6)10(12)13/h1-4H,5H2 | | InChIKey | GZHPNIQBPGUSSX-UHFFFAOYSA-N | | SMILES | [O-][N+](=O)c1cccc(c1)C(=O)CBr | | CAS DataBase Reference | 2227-64-7(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Bromo-3'-nitroacetophenone(2227-64-7) |
| 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 | Skin Corr. 1B |
| | 3-Nitrophenacylbromide Usage And Synthesis |
| Chemical Properties | beige-orange to yellow-green crystalline powder | | Uses | 2-Bromo-3′-nitroacetophenone may be used in the preparation of 2-bromo-3′-nitroacetophenone. It may be used in the preparation of 2-hydroxy-ethyl-1-[(3-nitro-phenyl)-2-oxoethyl]-piperidinium bromide. | | General Description | Debromination of 2-bromo-3′-nitroacetophenone in various solvents has been reported. | | Synthesis | The general procedure for the synthesis of 2-bromo-3'-nitroacetophenone from m-nitroacetophenone is as follows: preparation of 2-bromo-1-(3-nitrophenyl)acetophenone (2a-1). Aluminum chloride (0.16 g, 1.20 mmol) was added to a suspension of commercially available 3-nitroacetophenone (4.82 g, 29.19 mmol) in anhydrous ether (25 mL). The reaction mixture was cooled to 0 °C, followed by the slow dropwise addition of bromine (1.50 mL, 29.19 mmol). The reaction mixture was stirred at room temperature for 1 h until complete conversion of the feedstock (monitored by 1H NMR) and the reaction was quenched quickly to avoid dibromide formation. After addition of water (30 mL), the mixture was extracted with ether (3 x 30 mL) and dried over anhydrous magnesium sulfate to afford compound 2a-1 as a yellow-brown solid (5.73 g, 97% yield).1H NMR (CDCl3, 200 MHz): δ 4.50 (s, 2H, H1), 7.73 (t, J = 8.0 Hz, 1H, H7), 8.31 ( ddd, J = 7.8, 1.7, 1.1 Hz, 1H, H8), 8.43 (ddd, J = 8.2, 2.3, 1.1 Hz, 1H, H6), 8.76 (t, J = 1.9 Hz, 1H, H4).13C NMR (CDCl3, 200 MHz): δ 30.4, 123.9, 128.2, 130.4, 134.6, 135.2, 148.6, 189.5. MS-ESI (m/z): [M + H]+ = 244.9. | | References | [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8276 - 8292
[2] Patent: WO2017/17004, 2017, A1. Location in patent: Page/Page column 17
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2192 - 2196
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 10, p. 1424 - 1430 |
| | 3-Nitrophenacylbromide Preparation Products And Raw materials |
|