4-Bromo-2,6-difluoroaniline Chemical Properties

Melting point:

63-65 °C (lit.)

Boiling point:

188.2±35.0 °C(Predicted)

Density 

1.788±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

1.11±0.10(Predicted)

form 

Crystalline Powder

color 

Brown

InChI

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

InChIKey

BFQSQUAVMNHOEF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

67567-26-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29214200

MSDS

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

4-Bromo-2,6-difluoroaniline Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

4-Bromo-2,6-difluoroaniline was used in synthesis of:

• ammonium 5-bromo-7-fluorobenzo-2-oxa-1,3-diazole-4-sulphonate, fluorogenic derivatizating reagent for the determination of aminothiols by HPLC
• olefin tolanes
• 1-(4-amino-3,5-difluoro)-2-(4-butyloxyphenyl)ethyne
• 4′′-n-butyloxy-3,5-difluoroterphenyl-4-amine
• 4-(3-methylbut-1-yn-3-ol)-2,6-difluoroaniline

Uses

4-Bromo-2,6-difluoroaniline is used in the preparation of potent, VEGF receptor tyrosine kinase inhibitors.

Synthesis

b) Preparation of Intermediate 2: Dissolve 2,6-difluoroaniline (3.0 g, 22.56 mmol) in acetic acid (10 mL). Bromine (1.2 mL) was slowly added dropwise to the above solution. The reaction mixture was stirred at room temperature for 15 minutes. After the reaction was completed, the solvent was evaporated under reduced pressure. The residue was neutralized with aqueous sodium carbonate and the aqueous phase was subsequently extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give Intermediate 2 in 92% yield.

References

[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1544 - 1547
[2] Angew. Chem., 2016, vol. 128, # 4, p. 1569 - 1573,5
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5326 - 5333
[4] Patent: WO2006/15985, 2006, A1. Location in patent: Page/Page column 54
[5] Patent: US6716491, 2004, B2

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