3-Fluoro-4-nitrotoluene
[CAS# 446-34-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Nitro compound
• Name: 3-Fluoro-4-nitrotoluene
• Synonyms: 2-fluoro-4-methyl-1-nitrobenzene
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.13
• CAS Registry Number: 446-34-4
• EC Number: 207-166-5
• SMILES: CC1=CC(=C(C=C1)[N+](=O)[O-])F

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.438 g/mL (Expl.)
• Melting point: 52-55 °C (Expl.)
• Index of Refraction: 1.53, Calc.^*
• Boiling Point: 258.6 °C (760 mmHg), Calc.^*, 287.9-289.4 °C (Expl.)
• Flash Point: 104.1±21.8 °C, Calc.^*, 110 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-Fluoro-4-nitrotoluene is an aromatic compound consisting of a toluene backbone with a fluorine atom at the 3-position and a nitro group at the 4-position. This compound belongs to a family of substituted toluenes, which are important intermediates in organic synthesis and industrial applications due to their reactivity and versatility.

The synthesis of 3-fluoro-4-nitrotoluene typically involves selective substitution reactions of toluene derivatives. The presence of the nitro group (-NO₂) and the fluorine atom (-F) on the aromatic ring significantly influences the chemical reactivity of the molecule, making it useful in various synthetic processes. The nitro group is an electron-withdrawing group that increases the electrophilicity of the ring, making it more reactive toward nucleophilic substitution reactions, while the fluorine atom is an electron-withdrawing substituent that can also modify the molecule's physical and chemical properties.

3-Fluoro-4-nitrotoluene has been used in the preparation of other complex organic compounds, including pharmaceuticals, agrochemicals, and materials. Its reactive nature makes it a valuable building block for the introduction of functional groups into organic molecules. The compound is often used in the synthesis of other fluorinated compounds and nitroaromatic derivatives, which may have various industrial or pharmaceutical applications.

In the field of materials science, 3-fluoro-4-nitrotoluene is sometimes utilized as a precursor in the synthesis of polymers or materials that require specific electronic or physical properties. Additionally, due to the presence of both a nitro group and a fluorine atom, it can be employed in the design of compounds with unique electronic properties, which are useful in the development of materials for electronic or optoelectronic applications.

The chemical properties of 3-fluoro-4-nitrotoluene, specifically its reactivity in substitution reactions, make it valuable for the development of more complex structures in both laboratory and industrial settings. The synthesis of fluorinated compounds, in particular, is of interest in medicinal chemistry, where the addition of a fluorine atom can enhance the metabolic stability or bioactivity of certain compounds.

Overall, 3-fluoro-4-nitrotoluene is an important intermediate in organic synthesis with applications in the creation of complex organic molecules, pharmaceuticals, and materials. Its reactivity and functional group positioning make it an essential building block in both industrial and laboratory chemical processes.

References

2020. A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3′-[oxybis(methylene)]bis(9-methoxy-9H-carbazole). Frontiers of Chemical Science and Engineering, 15(3).
DOI: 10.1007/s11705-020-1979-9

2022. Palladium-Catalyzed Cross Coupling of N-Tosylhydrazones with Aryl Halides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-01342