2-Fluoro-4-nitrotoluene Chemical Properties

Melting point:

31-35 °C (lit.)

Boiling point:

65-68 °C/2 mmHg (lit.)

Density 

1.3021 (estimate)

Flash point:

165 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Low Melting Solid

color 

Yellow to brown

Water Solubility 

Insoluble in water. Solubility in methanol gives very faint turbidity.

FreezingPoint 

32.0 to 35.0 ℃

BRN 

2250156

InChI

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

InChIKey

WIQISTBTOQNVCE-UHFFFAOYSA-N

SMILES

C1(C)=CC=C([N+]([O-])=O)C=C1F

CAS DataBase Reference

1427-07-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 2-fluoro-1-methyl-4-nitro-(1427-07-2)

Safety Information

Hazard Codes 

Xn,Xi,F

Risk Statements 

20/21/22-36/37/38-11

Safety Statements 

26-36/37/39

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049085

MSDS

• Language:English Provider:2-Fluoro-4-nitrotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Fluoro-4-nitrotoluene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Fluoro-4-nitrotoluene was used in the synthesis of 2-fluoro-4-nitrobenzoic acid.

Synthesis

General procedure for the synthesis of 2-fluoro-4-nitrotoluene from 4-nitrotoluene: To a three-necked flask equipped with an argon inlet and a thermometer was added a solution of anhydrous acetonitrile (15 mL) of 4-nitrotoluene (10 mmol). Subsequently, bis(trifluoroethoxy)phenyl iodide(III) tetrafluoroborate (BTFE, 2.0 g, 14 mmol) was added. The reaction mixture was cooled to -35 °C under argon protection and xenon difluoride (XeF2, 2.05 g, 12.5 mmol) was added in batches. The mixture was slowly warmed to -25 °C and stirred at this temperature for 30 min, then continued to warm to 20 °C, held for 1 h and stirred for another 1 h (the reaction progress was monitored by gas chromatography). After completion of the reaction, saturated sodium bicarbonate solution was added slowly to the reaction mixture until no gas was produced. The reaction mixture was extracted with ether (3 x 20 mL), the organic phases were combined, washed with water and dried with anhydrous sodium sulfate. For the reaction products of benzene (1), toluene (3) and chlorobenzene (4), the ether extracts were molecularly distilled and fractionated, and the fractions were analyzed by gas chromatography and NMR spectroscopy. For the reaction products of bromobenzene (5), nitrobenzene (6), p-nitrotoluene (7), and p-nitroanisole (8), the ether extracts were concentrated under vacuum at less than 25 °C, and the residue was dissolved in chloroform and separated by fast column chromatography (eluent was hexane-chloroform, 3:1). The eluate was concentrated at atmospheric pressure and the residue was analyzed by NMR spectroscopy. For the reaction product of iodobenzene (15), the precipitate formed after neutralization with sodium bicarbonate solution was filtered, washed with water, and the filtrate was washed sequentially with acetonitrile (5 mL) and ether (5 mL), and the solid was dried in air to give 1.1 g of solid residue, which according to NMR spectroscopy data was a mixture of 76% iodobenzene (16) and 24% (4-iodophenyl)phenyliodonium tetrafluoroborate ( 17) comprising a mixture. The organic filtrate was evaporated and the residue was treated with chloroform to give 100 mg of compound 18 with a melting point of 149 °C (literature value: 147-149 °C).

References

[1] Journal of Fluorine Chemistry, 2000, vol. 102, # 1-2, p. 169 - 173
[2] Russian Chemical Bulletin, 2015, vol. 64, # 5, p. 1049 - 1052
[3] Izv. Akad. Nauk, Ser. Khim., 2015, # 5, p. 1049 - 1052,4

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