| Identification | More | [Name]
5-FLUORO-2-METHOXYACETOPHENONE | [CAS]
445-82-9 | [Synonyms]
1-(5-FLUORO-2-METHOXYPHENYL)ETHANONE
5'-FLUORO-2'-METHOXYACETOPHENONE
5-FLUORO-2-METHOXYACETOPHENONE | [Molecular Formula]
C9H9FO2 | [MDL Number]
MFCD00671763 | [Molecular Weight]
168.16 | [MOL File]
445-82-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
23 °C | [Boiling point ]
132 °C(Press: 13 Torr) | [density ]
1.1880 | [refractive index ]
1.5180 | [Fp ]
110 °C | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
liquid | [Appearance]
Colorless to off-white <23°C Solid,>23°C Liquid | [InChI]
1S/C9H9FO2/c1-6(11)8-5-7(10)3-4-9(8)12-2/h3-5H,1-2H3 | [InChIKey]
CNVGMLMIQIPAFY-UHFFFAOYSA-N | [SMILES]
COc1ccc(F)cc1C(C)=O | [CAS DataBase Reference]
445-82-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2914790090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 |
| Hazard Information | Back Directory | [Uses]
5′-Fluoro-2′-methoxyacetophenone is used to synthesize other fluorinated compounds. | [Reactions]
5′-Fluoro-2′-methoxyacetophenone is a reactive intermediate that undergoes an electrophilic aromatic substitution with methanol to form the corresponding fluorinated methoxyacetophenone.
| [Synthesis]
Step 2. A 4.1:1 mixture of 5-fluoro-2-hydroxyacetophenone (10.4 g, 61.8 mmol) and dimethyl sulfate (2.54 g, 16.5 mmol) was dissolved in acetone (50 mL) and potassium carbonate (2.50 g, 18.1 mmol) was added. Dimethyl sulfate (0.25 mL, 2.6 mmol) was then added. The reaction mixture was heated to reflux for 18 h. After cooling to room temperature, water (20 mL) was added. The mixture was stirred for 3 hours at room temperature and then partitioned between dichloromethane (50 mL) and brine (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 13.0 g (98% yield, 97% area) of 2-methoxy-5-fluoroacetophenone was obtained as a yellow oil.NMR (400 MHz, CDCl3) δppm: 2.64 (s, 3H), 3.92 (s, 3H), 6.94 (dd, J=9.09,4.04 Hz, 1H), 7.18 (ddd, J=9.09, 7.33,3.28 Hz, 1H), 7.48 (dd, J=8.97,3.16 Hz, 1H); HPLC retention time: 3.39 min; MS (ESI+) C9H9FO2 m/z 169.1 (M+H)+. | [References]
[1] Patent: WO2018/161008, 2018, A1. Location in patent: Paragraph 00217
[2] Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020
[3] Patent: US4251546, 1981, A |
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