2,4,6-Trifluoronitrobenzene

CAS Number 315-14-0

Chemistry Building Blocks, Fluorinated Building Blocks, Materials, Monomers

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

A polyfluorinated building block

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

Specifications | MSDS | Literature and Reviews

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

For facile synthesis

Worldwide shipping

Quick and reliable shipping

Fluorinated nitrobenzene building block

For drug discoveries, dyes, and semiconductors

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

Product Details

Purity	>98%
Boiling Point	T_b = 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-Trifluoronitrobenzene MSDS Sheet

Literature and Reviews

An unprecedented azobenzene-based organic single-component ferroelectric, H. Peng et al., Chem. Sci., 13, 4936–4943(2022); DOI: 10.1039/d2sc00689h.
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.
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.

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.
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.
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.