| Identification | Back Directory | [Name]
3-FLUORO-4-NITRO-BENZALDEHYDE | [CAS]
160538-51-2 | [Synonyms]
uoro-4-nitrobenzenecarbaL
3-floro-4-nitrobenzaldehyde
2-Fluoro-4-formylnitrobenzene
3-FLUORO-4-NITRO-BENZALDEHYDE
Benzaldehyde, 3-fluoro-4-nitro-
3-Fluoro-4-nitrobenzaldehyde 98%
3-FLUORO-4-NITROBENZENECARBALDEHYDE | [Molecular Formula]
C7H4FNO3 | [MDL Number]
MFCD00968940 | [MOL File]
160538-51-2.mol | [Molecular Weight]
169.11 |
| Chemical Properties | Back Directory | [Melting point ]
57-58 | [Boiling point ]
312℃ | [density ]
1.443 | [Fp ]
143℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
powder to crystal | [color ]
Light yellow to Amber | [InChI]
InChI=1S/C7H4FNO3/c8-6-3-5(4-10)1-2-7(6)9(11)12/h1-4H | [InChIKey]
BWUIGISQVCIQBT-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C([N+]([O-])=O)C(F)=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
3-fluoro-4-nitrobenzaldehyde is a strong, oxidizing agent with a pungent odor that is soluble in organic solvents.
| [Uses]
3-fluoro-4-nitrobenzaldehyde is resistant to oxidation by acids and bases and can be used for the synthesis of cytomegalovirus (CMV) inhibitors.
| [Synthesis]
General procedure for the synthesis of 3-fluoro-4-nitrobenzaldehyde from 3-fluoro-N-methoxy-N-methyl-4-nitrobenzamide: 3-fluoro-N-methoxy-N-methyl-4-nitrobenzamide was added to 800 mL of tetrahydrofuran (THF) under ice-salt/water bath cooling conditions. Subsequently, a THF solution of 1 M diisobutylaluminum hydride (DIBAL) was slowly added through the addition funnel over 30 min. The reaction mixture was stirred under nitrogen (N2) protection for 1 hour. Upon completion of the reaction, the reaction mixture was carefully diluted with 1N hydrochloric acid (500 mL) and ethyl acetate (EtOAc, 500 mL) and then transferred to a separatory funnel for separation. The organic phase was washed sequentially with 1N hydrochloric acid (3 × 250 mL), 1N sodium hydroxide (2 × 250 mL) and water (250 mL). All aqueous layers were back-extracted with ethyl acetate (2 × 250 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated in vacuum to give 67 g of the target product 3-fluoro-4-nitrobenzaldehyde (396 mmol, 88% yield). The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H-NMR, DMSO-d6): δ 10.06 (s, 1H), 8.36-8.32 (t, J = 7.8 Hz, 1H), 8.06-8.03 (d, J = 11.2 Hz, 1H), 7.95-7.93 (d, J = 9.1 Hz, 1H). | [References]
[1] Patent: WO2005/121147, 2005, A1. Location in patent: Page/Page column 106 |
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