2-NITRO-5-FLUOROBENZOIC ACID, METHYL ESTER Chemical Properties

Melting point:

40-42°C

Boiling point:

282℃

Density 

1.388

Flash point:

124℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetone, DMSO

form 

Low Melting Solid

color 

White

Water Solubility 

Slightly soluble in water. Soluble in dimethyl sulfoxide and acetone.

InChI

InChI=1S/C8H6FNO4/c1-14-8(11)6-4-5(9)2-3-7(6)10(12)13/h2-4H,1H3

InChIKey

LCAUVFVOLNRVKG-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2916399090

2-NITRO-5-FLUOROBENZOIC ACID, METHYL ESTER Usage And Synthesis

Chemical Properties

Off-White to Yellow Solid

Uses

2-Nitro-5-fluorobenzoic Acid, Methyl Ester (cas# 393-85-1) is a compound useful in organic synthesis.

Synthesis

4-Fluoro-2-nitrobenzoic acid (4 g, 21.6 mmol) was dissolved in 40 mL of methanol at 0 °C and 8.0 mL of concentrated sulfuric acid was slowly added. The reaction mixture was warmed to 60 °C and stirred continuously for 16 hours. Upon completion of the reaction, it was cooled to room temperature and the pH was adjusted with aqueous potassium carbonate to 8. Subsequently, the organic solvent was evaporated under reduced pressure. The remaining aqueous phase was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. Finally, the organic phase was concentrated under reduced pressure to afford the red oily product methyl 2-nitro-5-fluorobenzoate (3.6 g, 82% yield). Mass spectrometry (ESI positive ion mode): m/z = 200 [M + H]+. LC-MS analytical conditions [Method 4, gradient elution: starting solvent water (containing 0.05% trifluoroacetic acid)-acetonitrile, initial acetonitrile ratio 10%]: retention time Rt = 1.01 min.

References

[1] Patent: WO2018/172250, 2018, A1. Location in patent: Page/Page column 385-386
[2] Patent: US2010/280268, 2010, A1. Location in patent: Page/Page column 57
[3] Patent: US2010/249158, 2010, A1. Location in patent: Page/Page column 16
[4] Patent: EP1810969, 2007, A1. Location in patent: Page/Page column 58

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