| Identification | More | [Name]
4'-Fluoro-3'-nitroacetophenone | [CAS]
400-93-1 | [Synonyms]
1-(4-FLUORO-3-NITRO-PHENYL)-ETHANONE
4'-FLUORO-3'-NITROACETOPHENONE
4-FLUORO-3'-NITROACETOPHENONE
4-FLUORO-3-NITROACETOPHENONE
4'-fluoro-3'-nitroacetophenone,1-(3-nitro-4-fluorophenyl)ethanone
4'-fluoro-3'-nitroacetophenone | [EINECS(EC#)]
626-780-8 | [Molecular Formula]
C8H6FNO3 | [MDL Number]
MFCD00115369 | [Molecular Weight]
183.14 | [MOL File]
400-93-1.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow crystalline powder | [Melting point ]
47-51 °C | [Boiling point ]
118-120°C 0,8mm | [density ]
1.336±0.06 g/cm3(Predicted) | [Fp ]
118-120°C/0.8mm | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [color ]
Light yellow | [BRN ]
2211976 | [InChIKey]
PTCNZDJJIOLIKQ-UHFFFAOYSA-N | [CAS DataBase Reference]
400-93-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29143990 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow crystalline powder | [Uses]
4''-?Fluoro-?3''-?nitroacetophenone is used as reactant/reagent in preparation of substituted furans via copper-catalyzed radical addition of acetophenones to alkynes. | [Synthesis]
General procedure for the synthesis of 4-fluoro-3-nitroacetophenone from 4-fluoroacetophenone: 1-(4-fluorophenyl)ethanone (1.10 g, 7.97 mmol) was dissolved in concentrated H2SO4 (5 mL) under stirring conditions. Subsequently, a mixed acid consisting of concentrated HCl and concentrated H2SO4 (2 mL) was slowly added. HNO3 (1.50 mL) was added slowly and dropwise at -15°C. The reaction mixture was continued to be stirred at -15 °C for 80 min, after which it was poured into ice-cold H2O (120 mL) and extracted with EtOAc (2 × 100 mL). The organic layers were combined and washed sequentially with H2O (100 mL) and brine (100 mL), and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 100-200 mesh, 40% EtOAc in hexane solution) to afford 4-fluoro-3-nitroacetophenone (0.80 g, 55%) as an off-white solid.1H NMR (400 MHz, CDCl3) δ 2.64 (s, 3H), 7.39 (t, J=9.30 Hz, 1H), 8.20- 8.26 (m, 1H), 8.57-8.66 (m, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1725 - 1728
[2] Patent: WO2017/89453, 2017, A1. Location in patent: Page/Page column 55
[3] Patent: WO2007/103260, 2007, A1. Location in patent: Page/Page column 63-64
[4] Archiv der Pharmazie (Weinheim, Germany), 1957, vol. 290, p. 587,595
[5] Archiv der Pharmazie, 1963, vol. 296, p. 324 - 336 |
|
|