3,4,5-Trifluoronitrobenzene
[CAS# 66684-58-0]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoronitrobenzene series
• Name: 3,4,5-Trifluoronitrobenzene
• Synonyms: 1,2,3-Trifluoro-5-nitrobenzene; 1-Nitro-3,4,5-trifluorobenzene
• Molecular Formula: C₆H₂F₃NO₂
• Molecular Weight: 177.08
• CAS Registry Number: 66684-58-0
• EC Number: 266-447-0
• SMILES: C1=C(C=C(C(=C1F)F)F)[N+](=O)[O-]

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*, 1.52 g/mL (Expl.)
• Index of Refraction: 1.487, Calc.^*, 1.486 (Expl.)
• Boiling Point: 208.6±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 79.9±25.9 ºC, Calc.^*, 75 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H300-H302-H312-H315-H319-H332
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332

• Transport Information: UN 2810

Discovory and Applicatios

3,4,5-Trifluoronitrobenzene is an organic compound with the molecular formula C6H2F3NO2. It belongs to a class of compounds known as substituted nitrobenzenes, where three fluorine atoms are positioned at the meta positions relative to the nitro group on the benzene ring. This structure makes it a highly fluorinated aromatic compound, known for its distinctive chemical properties.

The compound is commonly synthesized through various electrophilic aromatic substitution reactions, where a nitro group is introduced to a fluorinated benzene ring. The presence of the three fluorine atoms at the meta positions increases the electron-withdrawing properties of the molecule, enhancing the reactivity of the nitro group. This specific substitution pattern influences the chemical behavior of 3,4,5-trifluoronitrobenzene, particularly its reactivity in nucleophilic substitution reactions.

3,4,5-Trifluoronitrobenzene is primarily used as an intermediate in organic synthesis, particularly in the development of fluorinated compounds. The combination of a nitro group with three fluorine atoms on the benzene ring provides a versatile scaffold for the creation of more complex organic molecules. This makes it a valuable building block in the synthesis of agrochemicals, pharmaceuticals, and materials science.

In the pharmaceutical industry, fluorinated compounds are highly sought after due to the unique properties imparted by the fluorine atoms. Fluorine substitution can improve the stability, bioavailability, and lipophilicity of molecules, making them more suitable for drug development. The presence of both nitro and fluorine groups in 3,4,5-trifluoronitrobenzene can influence the compound's potential to interact with biological targets, though its primary use is as a precursor in the synthesis of other fluorinated molecules.

In materials science, 3,4,5-trifluoronitrobenzene has potential applications in the creation of high-performance materials, particularly those requiring enhanced chemical resistance or thermal stability. The fluorine atoms contribute to the stability and resistance of polymers or coatings made from derivatives of this compound. Additionally, the compound's reactivity makes it useful in the synthesis of specialized materials for electronic devices and sensors.

Overall, 3,4,5-trifluoronitrobenzene is an important intermediate in the synthesis of fluorinated compounds, with applications in pharmaceuticals and materials science. The specific arrangement of the fluorine atoms and the nitro group make it a useful compound for a range of chemical transformations, driving its utilization in various industrial and research applications.

References

2007. Direct Fluorination with Elemental Fluorine. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-031-00005

2011. Addendum 2000-2008. Aromatic Hydroxyketones: Preparation and Physical Properties.
DOI: 10.1007/978-1-4020-9787-4_8

2018. Pibrentasvir. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0278