3-Fluoro-4-methylaniline Chemical Properties

Melting point:

30-32 °C (lit.)

Boiling point:

93°C 12mm

Density 

1.093 g/mL at 25 °C (lit.)

refractive index 

1.5385-1.5405

Flash point:

88 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump to clear liquid

pka

4.02±0.10(Predicted)

Specific Gravity

1.093

color 

Light yellow to Brown

BRN 

2715987

InChI

InChI=1S/C7H8FN/c1-5-2-3-6(9)4-7(5)8/h2-4H,9H2,1H3

InChIKey

MGRHBBRSAFPBIN-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(C)C(F)=C1

CAS DataBase Reference

452-77-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

36/37/38-23/24/25-20/21/22

Safety Statements 

45-36/37/39-26-36/37-36

RIDADR 

2811

WGK Germany 

3

RTECS 

XU6825000

Hazard Note 

Toxic/Irritant

HazardClass 

6.1(b)

PackingGroup 

I

HS Code 

29214300

MSDS

• Language:English Provider:3-Fluoro-p-toluidine
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Fluoro-4-methylaniline Usage And Synthesis

Chemical Properties

clear pale yellow to brownish liquid after melting

Characteristics

3-Fluoro-4-methylaniline is an amide and has anti-cancer properties.

Uses

3-Fluoro-4-methylaniline is a synthesized compound that is used to produce anti-cancer agents.

Synthesis

General procedure for the synthesis of 3-fluoro-4-methylaniline from 2-fluoro-4-nitrotoluene: Freshly distilled toluene (0.6 mL), aromatic nitro compounds (0.60 mmol), indium triiodide (InI3, 14.9 mg, 0.030 mmol) and 1,1,3,3-tetramethyldi siloxane (TMDS, 318 μL, 1.80 mmol). After sealing the vial with a polytetrafluoroethylene (PTFE) septum, the mixture was stirred at 60 °C (bath temperature) and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 5 mL of aqueous sodium bicarbonate (NaHCO3) was added to the mixture, which was then extracted with ethyl acetate (EtOAc, 3 × 6 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane-ethyl acetate, from 9:1 to 4:1) to obtain the target product 3-fluoro-4-methylaniline.

References

[1] Tetrahedron Letters, 2003, vol. 44, # 42, p. 7783 - 7787
[2] Synthesis (Germany), 2015, vol. 47, # 20, p. 3179 - 3185
[3] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
[4] Monatshefte fuer Chemie, 1959, vol. 90, p. 683,687
[5] Journal of the Chemical Society, 1949, p. Spl. 113

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