5-Fluoro-2-nitrotoluene Chemical Properties

Melting point:

28°C

Boiling point:

97-98 °C/10 mmHg (lit.)

Density 

1.272 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.527(lit.)

Flash point:

190 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow

Specific Gravity

1.272

BRN 

2046652

InChI

InChI=1S/C7H6FNO2/c1-5-4-6(8)2-3-7(5)9(10)11/h2-4H,1H3

InChIKey

JHFOWEGCZWLHNW-UHFFFAOYSA-N

SMILES

C1([N+]([O-])=O)=CC=C(F)C=C1C

CAS DataBase Reference

446-33-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 4-fluoro-2-methyl-1-nitro-(446-33-3)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-45-37-28A

RIDADR 

UN 2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049085

MSDS

• Language:English Provider:4-Fluoro-2-methyl-1-nitrobenzene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluoro-2-nitrotoluene Usage And Synthesis

Chemical Properties

colorless to light yellow liquid

Industrial uses

5-Fluoro-2-nitrotoluene can be used to synthesize 5-fluoro-2-nitrobenzaldehyde, and the resulting substance can be used as an intermediate in pharmaceutical chemistry and organic synthesis, and can be used to prepare herbicides, plant growth regulators, etc.

Synthesis

The general procedure for the synthesis of 5-fluoro-2-nitrotoluene from 3-fluorotoluene is as follows: 1-fluoro-3-methylbenzene (9) (30 g, 273 mmol) was added slowly and dropwise to a stirred 90% aqueous nitric acid solution (100 mL) at 0-5 °C. The reaction mixture was stirred for 0.5 min and poured into ice water. The aqueous phase was extracted with dichloromethane (3 x 50 mL), the organic phases were combined and washed with saturated aqueous sodium bicarbonate (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution gradient: 0.5% to 3.3% ethyl acetate in petroleum ether) to afford the target product 5-fluoro-2-nitrotoluene as a yellow oil (16 g, 38% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 2.64 (s, 3H), 7.01-7.06 (m, 2H), 8.07 (m, 1H).

References

[1] Patent: US2010/324043, 2010, A1. Location in patent: Page/Page column 26-27
[2] Chemische Berichte, 1929, vol. 62, p. 1804
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97
[4] Journal of Organic Chemistry, 1961, vol. 26, p. 3351 - 3356
[5] Patent: US6020379, 2000, A

5-Fluoro-2-nitrotoluene (446-33-3)Related Product Information

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• 3-Nitrotoluene
• Methylparaben
• 4-Nitrotoluene
• 2-Nitro-4-methylsulfonyltoluene
• DINITROTOLUENE
• Kresoxim-methyl
• 2-Nitrotoluene
• Thiophanate-methyl
• Methyl
• Nitrobenzene
• 2,4,6-Trinitrotoluene
• Methyl bromide
• Fluorine
• 5-Fluoro-2-nitrobenzotrifluoride
• 2,4-DINITRO-5-FLUOROTOLUENE
• 5-Fluoro-2-nitrobenzadehyde
• 5-FLUORO-2-NITROPHENYLACETONITRILE