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247979

Sigma-Aldrich

1-Bromo-2,4,5-trifluorobenzene

99%

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Linear Formula:
BrC6H2F3
CAS Number:
327-52-6
Molecular Weight:
210.98
EC Number:
206-318-8
MDL number:
MFCD00000306
UNSPSC Code:
12352100
PubChem Substance ID:
24854904
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.485 (lit.)

bp

144 °C (lit.)

mp

−19 °C (lit.)

solubility

water: insoluble

density

1.802 g/mL at 25 °C (lit.)

SMILES string

Fc1cc(F)c(Br)cc1F

InChI

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

InChI key

DVTULTINXNWGJY-UHFFFAOYSA-N

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General description

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

Application

1-Bromo-2,4,5-trifluorobenzene has been used in the synthesis of:
  • 3-ethenyl, 3-ethynyl, 3-aryl and 3-cyclopropyl-2,4,5-trifluorobenzoic acids
  • 3-bromo-2,5,6-trifluorobenzoic acid and 2,4,5-trifluorobenzoic acid

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

132.8 °F

Flash Point(C)

56 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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3-Ethenyl, 3-ethynyl, 3-aryl, and 3-cyclopropyl-2, 4, 5-trifluorobenzoic acids: Useful intermediate in the synthesis of quinolone antibacterials.
Turner WR and Suto MJ.
Tetrahedron Letters, 34(2), 281-284 (1993)
A dramatic solvent effect during aromatic halogen-metal exchanges. Different products from lithiation of polyfluorobromobenzenes in ether and tetrahydrofuran.
Bridges AJ, et al.
The Journal of Organic Chemistry, 55(2), 773-775 (1990)
Bromine-magnesium-exchange as a general tool for the preparation of polyfunctional aryl and heteroaryl magnesium-reagents.
Abarbri M, et al.
Tetrahedron Letters, 40(42), 281-284 (1999)
Chan Seok Oh et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(2), 642-648 (2018-10-20)
Blue thermally activated delayed fluorescent (TADF) devices with short excited-state lifetime, high reverse intersystem crossing rate, and low-efficiency roll-off were developed by managing the molecular structure of donor-acceptor-type blue emitters. Three isomers of blue TADF emitters with a diphenyltriazine acceptor

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