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263443

Sigma-Aldrich

1-Bromo-2,4-difluorobenzene

98%

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Linear Formula:
BrC6H3F2
CAS Number:
348-57-2
Molecular Weight:
192.99
Beilstein:
1680892
EC Number:
206-479-4
MDL number:
MFCD00000330
UNSPSC Code:
12352100
PubChem Substance ID:
24855973
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.505 (lit.)

bp

145-146 °C (lit.)

mp

−4 °C (lit.)

density

1.708 g/mL at 25 °C (lit.)

SMILES string

Fc1ccc(Br)c(F)c1

InChI

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

InChI key

MGHBDQZXPCTTIH-UHFFFAOYSA-N

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General description

1-Bromo-2,4-difluorobenzene undergoes lithiation exclusively at the position having two adjacent halogen substituents, to yield 6-bromo-2,3-difluorobenzoic acid.

Application

1-Bromo-2,4-difluorobenzene has been used in:
  • preparation of (2S)-1-(2,4-difluorophenyl)-2-(1,1-dimethyl-1-sila-ethoxy)-propan-1-one
  • enantiomeric preparation of the key intermediate of chiral azole antifungal agents by a chemoenzymatic process

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)

125.6 °F

Flash Point(C)

52 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Regioselective ortho-lithiation of chloro and bromo substituted fluoroarenes.
Mongin F and Schlosser M.
Tetrahedron Letters, 37(36), 6551-6554 (1996)
A practical chemoenzymatic synthesis of a key intermediate of antifungal agents.
Yasohara Y, et al.
Tetrahedron Letters, 42(19), 3331-3333 (2001)
Ram Shankar Upadhayaya et al.
Bioorganic & medicinal chemistry, 12(9), 2225-2238 (2004-04-15)
A series of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-[2-[4-aryl-piperazin-1-yl]-ethyl]-tetrazol-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-[2-[4-aryl-piperazin-1-yl]-ethyl]-tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl
Ji Gwang Yu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(63), 16044-16050 (2017-08-24)
Four dibenzofuran-type host materials substituted with a carbazolylcarbazole moiety were synthesized to investigate the effect of substitution position on the material parameters and device performances of host materials. The carbazolylcarbazole moiety was substituted at the 1-, 2-, 3-, and 4-positions

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