| Identification | More | [Name]
4-Fluoro-3-methoxyaniline | [CAS]
64465-53-8 | [Synonyms]
3-METHOXY-4-FLUOROANILINE
4-FLUORO-3-METHOXYANILINE
BUTTPARK 14\01-65
4-Fluoro-3-Methoxybenzenamin
4-FLUORO-3-METHOXYBENZENAMINE
4-Fluoro-3-methoxyphenylamine
2-fluoro-5-aminoanisole(4-fluoro-3-methoxyaniline) | [Molecular Formula]
C7H8FNO | [MDL Number]
MFCD00665789 | [Molecular Weight]
141.14 | [MOL File]
64465-53-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
66-68 | [Boiling point ]
135 °C(Press: 18 Torr) | [density ]
1.176±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
solid | [pka]
4.23±0.10(Predicted) | [color ]
Brown to black | [InChI]
InChI=1S/C7H8FNO/c1-10-7-4-5(9)2-3-6(7)8/h2-4H,9H2,1H3 | [InChIKey]
XAACOEWSHBIFGJ-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(F)C(OC)=C1 | [CAS DataBase Reference]
64465-53-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H315-H318-H335-H412 | [Precautionary statements ]
P261-P273-P280-P301+P312-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [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 . | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2922290090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 3
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
4-Fluoro-3-methoxyaniline serves as a precursor in the synthesis of 4-trifluoromethyl-4,5-dihydro-1H-pyrrole derivatives, formed by reacting with substituted β-oxoamides (such as N-(4-fluoro-3-methoxyphenyl)-3-oxobutanamide) and 3-bromo-1,1,1-trifluoropropan-2-one[4]. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 46, p. 2520, 1981 DOI: 10.1021/jo00325a017 | [Synthesis]
General procedure for the synthesis of 4-fluoro-3-methoxyaniline from 2-fluoro-5-nitroanisole:
1. Reduction of nitro: The nitro compound 2-fluoro-5-nitroanisole (6.5 g, 0.038 mol) and iron powder (10.6 g, 0.19 mol) were suspended in ethanol (90 ml) and heated to 50 °C. Concentrated hydrochloric acid (120 ml) was added dropwise to the reaction mixture at 0°C. The reaction mixture was stirred at 20°C for 18 hours.
2. Post-treatment: the reaction mixture was filtered through diatomaceous earth and the filter cake was washed repeatedly with ethanol. The filtrate and washings were combined and concentrated under reduced pressure to remove ethanol. The residue was alkalized to pH neutral with solid Na2CO3.
3. Extraction and purification: Extract the alkalized aqueous phase with ethyl acetate and combine the organic phases. The organic phase was washed with water and saturated saline in turn, and then dried with anhydrous Na2SO4. The drier was removed by filtration, and the organic phase was concentrated under reduced pressure to obtain 4-fluoro-3-methoxyaniline (5g, 93% yield).
Product characterization: HPLC-MS showed a purity of 97% and a molecular ion peak (M+1) of 142.1. | [References]
[1] Patent: WO2017/132928, 2017, A1. Location in patent: Paragraph 000101
[2] Patent: WO2010/145989, 2010, A1. Location in patent: Page/Page column 12-13
[3] Patent: US4044049, 1977, A
[4] Patent: US4044049, 1977, A |
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