1-Bromo-2,5-difluorobenzene Chemical Properties

Melting point:

−31 °C(lit.)

Boiling point:

58-59 °C20 mm Hg(lit.)

Density 

1.708 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.508(lit.)

Flash point:

149 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

Specific Gravity

1.708

color 

Colorless to Light yellow to Light orange

Water Solubility 

Insoluble

BRN 

1680893

InChI

InChI=1S/C6H3BrF2/c7-5-3-4(8)1-2-6(5)9/h1-3H

InChIKey

XCRCSPKQEDMVBO-UHFFFAOYSA-N

SMILES

C1(F)=CC=C(F)C=C1Br

CAS DataBase Reference

399-94-0(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 2-bromo-1,4-difluoro-(399-94-0)

Safety Information

Hazard Codes 

Xi,F,Xn

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-2637/39-37/39

RIDADR 

UN 2922

WGK Germany 

3

Hazard Note 

Flammable

HazardClass 

IRRITANT, FLAMMABLE

HS Code 

29039990

MSDS

• Language:English Provider:2-Bromo-1,4-difluorobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-Bromo-2,5-difluorobenzene Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

2-Bromo-1,4-difluorobenzene has been used in the preparation of 1,4-difluoroanthraquinone, a precursor to ametantrone.

General Description

Lithiation of 2-bromo-1,4-difluorobenzene in the presence of lithium diisopropylamide (LDA) in THF-hexane, butyllithium in diethyl ether-hexane and butyllithium in THF-hexane has been reported.

Synthesis

GENERAL STEPS: In a FEP or PFA reactor equipped with a PTFE-lined magnetic stir bar and connected to a gas scrubber bottle, substituted benzene (0.95-1.10 mmol), 1,1,1,3,3-pentafluorobutane (2 mL per mL of C6H5R), and BF3-Et2O (1.3-1.5 mmol/mmol C6H5R) were added. The mixture was stirred at 0-5 °C (ice bath) for 10-15 min, followed by batchwise addition of XeF2 (1.2-1.3 mmol/mmol C6H5R). After each addition, the mixture was stirred at 22-25 °C for 3-5 min and cooled to 0-5 °C again. After the addition was completed, the dark-colored solution was continued to be stirred at 22-25 °C for 15-30 min. Upon completion of the reaction, the reaction was quenched by the addition of 10% aqueous KHCO3, the upper organic layer was separated and filtered through a short column packed with silica gel (40-60 μm) and finally dried with magnesium sulfate. The solution was analyzed by 19F NMR and GC/MS. The major products are listed in the table and the others are as follows (GC/MS data provided).

References

[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1400 - 1407
[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1412 - 1419,8

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