4-FLUORO-3-NITROBENZALDEHYDE Chemical Properties

Melting point:

45-47 °C (lit.)

Boiling point:

286.0±25.0 °C(Predicted)

Density 

1.443±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

White to tan

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H4FNO3/c8-6-2-1-5(4-10)3-7(6)9(11)12/h1-4H

InChIKey

ILKWFRCNNILIJW-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(F)C([N+]([O-])=O)=C1

CAS DataBase Reference

42564-51-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-22

WGK Germany 

3

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich

4-FLUORO-3-NITROBENZALDEHYDE Usage And Synthesis

Chemical Properties

White to tan crystalline powder

Uses

4-Fluoro-3-nitrobenzaldehyde is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

General procedure for the synthesis of 4-fluoro-3-nitrobenzaldehyde from 3-nitro-4-fluorobenzyl alcohol: a dimethyl sulfoxide (12 mL) suspension of the pyridine-sulfur trioxide complex (4.65 g, 29.2 mmol) was added to a solution containing 4-fluoro-3-nitrobenzyl alcohol (1.0 g, 5.84 mmol) and triethylamine (4.07 mL, 29.2 mmol) in a dichloromethane (20 mL) solution. The reaction mixture was stirred at room temperature for 15 minutes. After completion of the reaction, the reaction solution was diluted with ether (150 mL), washed sequentially with water, 5% potassium bisulfate solution and water, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (5:1)] to afford colorless crystalline 4-fluoro-3-nitrobenzaldehyde (0.86 g, 87% yield). The melting point of the product was 37-38 °C. 1H-NMR (CDCl3) δ: 7.51 (1H, t, J = 9.4 Hz), 8.10-8.30 (1H, m), 8.60 (1H, dd, J = 7.4, 2.2 Hz), 10.05 (1H, s).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5546 - 5550
[2] Patent: US2003/78251, 2003, A1
[3] Patent: WO2015/57938, 2015, A1. Location in patent: Page/Page column 52
[4] Patent: CN107400092, 2017, A. Location in patent: Paragraph 0293; 0295; 0300-0302
[5] Patent: CN108264511, 2018, A. Location in patent: Paragraph 0280; 0283; 0288-0290

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