4-FLUORO-N-ISOPROPYLANILINE

4-FLUORO-N-ISOPROPYLANILINE Property

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

RIDADR 

2810

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2921490090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H317May cause an allergic skin reaction

H331Toxic if inhaled

H341Suspected of causing genetic defects

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P311Call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

4-FLUORO-N-ISOPROPYLANILINE Chemical Properties,Usage,Production

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