4-BROMO-2,5-DIFLUOROANILINE Chemical Properties

Melting point:

74-78 °C (lit.)

Boiling point:

212.1±35.0 °C(Predicted)

Density 

1.788±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

1.48±0.10(Predicted)

color 

White to Light yellow

BRN 

4741102

InChI

InChI=1S/C6H4BrF2N/c7-3-1-5(9)6(10)2-4(3)8/h1-2H,10H2

InChIKey

XOYHFIQPPOJMFK-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=C(Br)C=C1F

CAS DataBase Reference

112279-60-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-36/37/38

Safety Statements 

28-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-BROMO-2,5-DIFLUOROANILINE Usage And Synthesis

Chemical Properties

White solid

Synthesis

Example 14 Preparation of 4-bromo-2,5-difluoroaniline: To a stirred mixture of 100 g of 2,5-difluoroaniline and 1150 mL of acetic acid (AcOH) was slowly added 40.2 mL of bromine (Br2) in 350 mL of acetic acid (AcOH) over a period of 1.3 h. The reaction temperature was maintained at a temperature of between 15 °C and 20 °C. The reaction was carried out over a period of 2.3 hours. Upon completion of the reaction, the resulting pink suspension was continued to be stirred for 30 minutes, followed by vacuum evaporation to remove the solvent. The residue was alkalized with 50% sodium hydroxide (NaOH) solution (ice was added during the process to maintain the temperature below 35°C). The free base was extracted with 1 L of dichloromethane (CH2Cl2), and the extract was washed with 2 x 100 mL of water (H2O), dried over anhydrous sodium sulfate (Na2SO4), and finally the solvent was evaporated under vacuum to afford 157 g (97.5% yield) of the target product 4-bromo-2,5-difluoroaniline, with melting points ranging from 73°C to 75°C. Mass spectrometry analysis showed the M+1 ion peaks at 208 and 210.

References

[1] Patent: EP224001, 1991, B1
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64
[3] Journal of Materials Chemistry, 2004, vol. 14, # 11, p. 1731 - 1743
[4] Patent: EP329752, 1989, A1
[5] Patent: WO2013/142266, 2013, A1. Location in patent: Paragraph 00498

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