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2,4,6-Trifluoronitrobenzene

CAS Number 315-14-0

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers

2,4,6-Trifluoronitrobenzene CAS 315-14-0
Product Code B1851-5g
Price £74 ex. VAT
£ GBP

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A polyfluorinated building block

Used as a synthesis intermediate for azo and azide compounds in semiconductors and photonics applications

2,4,6-Trifluoronitrobenzene (CAS number 315-14-0) has three fluoro-substituents at the ortho- and para-position to the nitro group sitting at the benzene ring. 2,4,6-Trifluoronitrobenzene can be reduced to aniline, which allows further functionalization to obtain azo/azide compounds. To synthesize azo compounds, the building block is firstly converted to the diazonium salt, followed by an azo C-N coupling. Alternatively, a single-step oxidation of aniline to azo compound can be done with potassium permanganate and iron (II) sulfate as the oxidising agents. Azide compounds can be synthesized with triflyl azide and base via diazo transfer.

The corresponding azo-compounds are used in ferroelectric devices, azo-dye liquid crystals and photoswitches (light induced trans-cis transformation of azo). The corresponding azide compounds are readily to synthesis large chromophores by 1-3 dipolar cycloaddition (click reaction) for OLEDs and dye-sensitized solar cells (DSSCs).

The fluoro-substituents enable late-stage functionalization by nucleophilic aromatic substitution to expand the functionalities of the molecules. 2,4,6-Trifluoronitrobenzene is also used for the synthesis of fluorinated polytriarylamines (F-PTAAs) which find applications as hole transporting materials in organic electronics.

Multiple functional groups

Multiple functional groups

For facile synthesis

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Fluorinated building block

Fluorinated nitrobenzene building block

For drug discoveries, dyes, and semiconductors

High purity 315-14-0

High purity

>98% High purity

General Information

CAS Number 315-14-0
Chemical Formula C6H2F3NO2
Full Name 1,3,5-Trifluoro-2-nitrobenzene
Molecular Weight 177.08 g/mol
Synonyms N/A
Classification / Family Fluorinated building blocks, Dyes, Nitrobenzene derivatives, Semiconductors synthesis intermediates

Chemical Structure

2,4,6-Trifluoronitrobenzene chemical structure, CAS 315-14-0
2,4,6-Trifluoronitrobenzene chemical structure, CAS 315-14-0

Product Details

Purity >98%
Boiling Point Tb = 183.5 °C at 760 mmHg
Relative Density 1.514 g/mL at 25 °C
Appearance Colourless to slightly yellow liquid

MSDS Documentation

2,4,6-Trifluoronitrobenzene2,4,6-Trifluoronitrobenzene MSDS Sheet

Literature and Reviews

  1. An unprecedented azobenzene-based organic single-component ferroelectric, H. Peng et al., Chem. Sci., 13, 4936–4943(2022); DOI: 10.1039/d2sc00689h.
  2. Design and synthesis of visible-light-responsive azobenzene building blocks for chemical biology, J. Volarić et al., J. Org. Chem., 87, 14319−14333(2022); DOI: 10.1021/acs.joc.2c01777.
  3. Light-controlled lyotropic liquid crystallinity of polyaspartates exploited as photo-switchable alignment medium, M. Hirschmann et al., J. Am. Chem. Soc., 145(6), 3615–3623(2023); DOI: 10.1021/jacs.2c12760.
  4. o‐fluoroazobenzenes as readily synthesized photoswitches offering nearly quantitative two‐way isomerization with visible light, D. Bléger et al., J. Am. Chem. Soc., 134(51) 20597–20600(2012); DOI: 10.1021/ja310323y.
  5. Visible-light-controlled histone deacetylase inhibitors for targeted cancer therapy, L. Josa-Culleré et al., J. Med. Chem., 66, 1909−1927(2023); DOI: 10.1021/acs.jmedchem.2c01713.
  6. Triphenylamine-based organic dyes containing a 1,2,3-triazole bridge for dye-sensitized solar cells via a ‘Click’ reaction, T. Duan et al., Dyes and Pigm., 94, 28-33(2012); DOI: 10.1016/j.dyepig.2011.11.008.
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