2-Chloro-5-fluoroaniline Chemical Properties

Melting point:

26°C

Boiling point:

211°C

Density 

1.349±0.06 g/cm3(Predicted)

refractive index 

1.5560

Flash point:

211°C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

1?+-.0.10(Predicted)

color 

Colorless to Light yellow to Light orange

Water Solubility 

Insoluble in water.

FreezingPoint 

17.0 to 22.0 ℃

InChI

InChI=1S/C6H5ClFN/c7-5-2-1-4(8)3-6(5)9/h1-3H,9H2

InChIKey

VWUFOZAFKYOZJB-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=CC=C1Cl

CAS DataBase Reference

452-83-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

20/21/22-36/37/38-23/24/25-22-36/38-33

Safety Statements 

26-36/37/39-45-36/37-28

RIDADR 

UN2811

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

2-Chloro-5-fluoroaniline Usage And Synthesis

Chemical Properties

Yellowish oily liquid or crystal

Uses

2-Chloro-5-fluoroaniline is used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 2-chloro-5-fluoroaniline from 2-chloro-5-fluoronitrobenzene was as follows: a mixture of 0.17 g (1 mmol) of 2-chloro-5-fluoronitrobenzene, 1.13 g (5 mmol) of tin(II) chloride dihydrate, and 10 mL of ethanol was stirred for 0.5 hours at 70 °C. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into 30 mL of water, alkalized with 10% sodium carbonate solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 0.12 g (84.5% yield) of the target product 2-chloro-5-fluoroaniline. The structure of the product was confirmed by 1H-NMR (CDCl3, δ): 4.16 (single peak, 2H, NH2), 6.51-6.77 (multiple peaks, 2H, CH on the benzene ring), 7.09-7.21 (multiple peaks, 1H, CH on the benzene ring).

References

[1] Patent: EP1200406, 2004, B1. Location in patent: Page 14
[2] Green Chemistry, 2012, vol. 14, # 11, p. 3164 - 3174,11

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