1-Bromo-2,4,5-trifluorobenzene Chemical Properties

Melting point:

−19 °C(lit.)

Boiling point:

144 °C(lit.)

Density 

1.802 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.485(lit.)

Flash point:

132 °F

storage temp. 

2-8°C

solubility 

water: insoluble

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

1.81

Water Solubility 

insoluble

BRN 

1636588

InChI

InChI=1S/C6H2BrF3/c7-3-1-5(9)6(10)2-4(3)8/h1-2H

InChIKey

DVTULTINXNWGJY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

327-52-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-2,4,5-trifluoro-(327-52-6)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-10

Safety Statements 

26-36/37/39-37/39-16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Flammable

HazardClass 

3

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:1-Bromo-2,4,5-trifluorobenzene
• Language:English Provider:SigmaAldrich
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1-Bromo-2,4,5-trifluorobenzene Usage And Synthesis

Chemical Properties

clear slightly yellow liquid

Uses

1-Bromo-2,4,5-trifluorobenzene is the intermediate of liquid crystals. The derivatives of this compound can be used as intermediates for the synthesis of qunolone antibacterial. It is employed in the synthesis of 3-ethenyl, 3-ethynyl, 3-aryl, and 3-cyclopropyl-2, 4, 5-trifluorobenzoic acids from 1-bromo-2, 4, 5-trifluorobenzene and 2, 4, 5-trifluoro-3-hydroxybenzoic acid.

Uses

Intermediates of Liquid Crystals

Definition

ChEBI: 1-Bromo-2,4,5-trifluorobenzene is an organofluorine compound.

General Description

1-Bromo-2,4,5-trifluorobenzene undergoes Br-Mg-exchange reaction with i-PrMgBr in THF to yield organomagnesium compound.

Synthesis

The general procedure for the synthesis of 2,4,5-trifluorobromobenzene from 1,2,4-trifluorobenzene was as follows: 100 g of 1,2,4-trifluorobenzene and 3 g of tin tetrachloride-polystyrene complex were added to a 500 mL three-necked flask, and glacial acetic acid was used as the reaction solvent. At room temperature, 127 mL of liquid bromine was added slowly and dropwise. The reaction lasted for 2 h, during which the progress of the reaction was monitored by thin-layer chromatography (TLC), and after confirming that the ingredients were fully reacted, vacuum evaporation was performed to remove the glacial acetic acid. Subsequently, 500 mL of chloroform was added and the organic phase was washed with 3% dilute hydrochloric acid, followed by the addition of saturated sodium sulfite solution to remove residual bromine from the organic phase. After sequential washing, the organic phase was washed with saturated saline. Finally, the solvent was removed by distillation to afford 158 g of 2,4,5-trifluorobromobenzene in 98.7% yield and 99.6% purity as shown by gas chromatography analysis.

References

[1] Patent: CN107673951, 2018, A. Location in patent: Paragraph 0015; 0016; 0017; 0018
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 153
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 94,98

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