2-Fluoro-5-nitrotoluene Chemical Properties

Melting point:

38-40 °C (lit.)

Boiling point:

99-100 °C/13 mmHg (lit.)

Density 

1.3021 (estimate)

Flash point:

221 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump

color 

White to Light yellow to Green

BRN 

1940341

InChI

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

InChIKey

XUCYJGMIICONES-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

455-88-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-fluoro-2-methyl-4-nitro-(455-88-9)

EPA Substance Registry System

Benzene, 1-fluoro-2-methyl-4-nitro- (455-88-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39-22

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

T

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049090

MSDS

• Language:English Provider:2-Fluoro-5-nitrotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Fluoro-5-nitrotoluene Usage And Synthesis

Application

2-Fluoro-5-nitrotoluene can be used as a nonlinear optical material in optical devices for applications such as frequency doubling, optical modulation, and optical detection.

Chemical Properties

white to light yellow crystal powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 8448, 1998 DOI: 10.1021/jo981557o

Synthesis

General procedure for the synthesis of 2-fluoro-5-nitrotoluene from 2-chloro-5-nitrotoluene: To an oven-dried resealable reaction tube fitted with a stirrer were added aryl halide (20, 0.12 mmol), BrettPhos (6.4 mg, 0.012 mmol, 10 mol%), (COD)Pd(CH2TMS)2 (2.3 mg. 0.006 mmol, 5 mol%), AgF (23 mg, 0.18 mmol) and toluene (2 mL). The reaction tube was then sealed with a screw cap and removed from the glove box, wrapped in aluminum foil and placed in an oil bath preheated to the indicated temperature with thorough stirring. After 12 hours of reaction, the reaction tube was removed from the oil bath and cooled to room temperature. 4-Fluorotoluene (13.2 μL, 0.12 mmol, 1 eq.) and dodecane (27.3 μL, 0.12 mmol, 1 eq.) were added as internal standards. The reaction mixture was filtered through a glass filter fitted with Celite to remove all solids. Finally, the product yield was analyzed by 19F NMR (282 MHz) and the conversion was determined by GC.

References

[1] Patent: US2011/15401, 2011, A1. Location in patent: Page/Page column 17
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 315,316

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