| Identification | More | [Name]
2-Bromo-2'-nitroacetophenone | [CAS]
6851-99-6 | [Synonyms]
2-BROMO-2'-NITROACETOPHENONE
2'-NITROPHENACYL BROMIDE
-Bromo-2'-Nitroacetophenone
2-Bromo-2'-nitroacetophenone
1-(2-Nitrophenyl)-2-bromoethanone
2'-Nitro-α-bromoacetophenone | [Molecular Formula]
C8H6BrNO3 | [MDL Number]
MFCD00010294 | [Molecular Weight]
244.04 | [MOL File]
6851-99-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to pale yellow crystalline powder | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
White to pale yellow crystalline powder | [Uses]
2-Bromo-2′-nitroacetophenone, an electroactive derivative-forming reagent, was used as a precolumn reagent for preparing prostaglandin derivatives. | [Uses]
2-Bromo-2'-nitroacetophenone is used in the novel synthesis of 5-pyridylindolizine 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 |
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