4-FLUORO-N-ISOPROPYLANILINE Chemical Properties

Boiling point:

214℃

Density 

1.045

vapor pressure 

0.1-0.9Pa at 20-50℃

Flash point:

83℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

5.91±0.32(Predicted)

Appearance

Light brown to brown Liquid

InChI

InChI=1S/C9H12FN/c1-7(2)11-9-5-3-8(10)4-6-9/h3-7,11H,1-2H3

InChIKey

RMXBOQCXULAXBO-UHFFFAOYSA-N

SMILES

C1(NC(C)C)=CC=C(F)C=C1

LogP

2.3 at 23℃ and pH5.59

Surface tension

56.68mN/m at 989.9mg/L and 20℃

EPA Substance Registry System

Benzenamine, 4-fluoro-N-(1-methylethyl)- (70441-63-3)

Safety Information

RIDADR 

2810

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2921490090

4-FLUORO-N-ISOPROPYLANILINE Usage And Synthesis

Uses

4-Fluoro-N-isopropylaniline is an intermediate used in the synthesis of Flufenacet, a herbicide.

Synthesis

General procedure for the synthesis of 4-fluoro-N-isopropylaniline from 4-fluoroaniline: 22.2 g (0.2 mol) of 4-fluoroaniline and 17.6 mL (0.24 mol) of acetone were added to a 500 mL three-necked, round-bottomed flask, dissolved in 120 mL (2 mol) of glacial acetic acid, mechanically stirred, and cooled in an ice bath to about 10°C. The mixture was then purified to about 10°C with mechanical stirring. 9.4 g (0.25 mol) of sodium borohydride was added in batches while keeping the temperature below 20°C. After addition, the reaction mixture was stirred at 20°C for 30 minutes to 1 hour. Subsequently, the mixture was poured into 500 mL of ice water. The aqueous solution was made alkaline by dropwise addition of 120 mL of 50% aqueous sodium hydroxide (keeping the temperature below 25°C). The product was extracted with hexane (2 x 100 mL) and the organic phases were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a clarified liquid. The product was purified by distillation and the fraction with a boiling point of 40 °C/0.5 mmHg was collected to give 21.8 g of clarified colorless liquid product in 71% yield.

References

[1] Patent: US4418021, 1983, A
[2] Patent: US5616799, 1997, A

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