3-FLUORO-4-NITRO-BENZALDEHYDE Chemical Properties

Melting point:

57-58

Boiling point:

312℃

Density 

1.443

Flash point:

143℃

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2913000090

3-FLUORO-4-NITRO-BENZALDEHYDE Usage And Synthesis

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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