2-Fluorotoluene
[CAS# 95-52-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 2-Fluorotoluene
• Synonyms: o-Fluorotoluene
• Molecular Formula: C₇H₇F
• Molecular Weight: 110.13
• CAS Registry Number: 95-52-3
• EC Number: 202-428-5
• SMILES: CC1=CC=CC=C1F

Properties

• Density: 1.001
• Melting point: -62 °C
• Boiling point: 113-114 °C
• Refractive index: 1.472-1.474
• Flash point: 8 °C
• Water solubility: immiscible

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS07 Danger
• Risk Statements: H225-H301-H315-H319-H332-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 2388

Discovery and Applications

2-Fluorotoluene, a fluorinated aromatic hydrocarbon, represents a significant advancement in organic chemistry due to its unique chemical properties and diverse applications. Discovered in the early 20th century, this compound has since become a crucial reagent and intermediate in various chemical processes.

2-Fluorotoluene is characterized by a fluorine atom bonded to the second position of a toluene molecule, which itself consists of a benzene ring with a methyl group. This specific substitution imparts distinctive electronic and steric effects compared to other fluorotoluene isomers, influencing its reactivity and application in synthesis.

One of the primary applications of 2-fluorotoluene is in the synthesis of pharmaceuticals and agrochemicals. Its fluorine atom enhances the metabolic stability of compounds, making them more effective in biological systems. In the pharmaceutical industry, 2-fluorotoluene is used as an intermediate in the synthesis of various drugs, where it contributes to the development of molecules with improved potency and selectivity. For instance, the fluorine substitution can modify the electronic distribution of a molecule, thereby influencing its interaction with biological targets and potentially improving therapeutic outcomes.

In agrochemicals, 2-fluorotoluene serves as a building block for the synthesis of herbicides and pesticides. The fluorine atom's presence in these molecules can improve their stability and effectiveness, leading to more efficient crop protection solutions. This is particularly valuable in designing chemicals that are both effective against pests and less harmful to the environment.

Another significant application of 2-fluorotoluene is in the field of material science. It is used as a precursor in the synthesis of fluorinated polymers, which are known for their high chemical resistance, thermal stability, and low surface energy. These properties make fluorinated polymers suitable for applications in coatings, films, and advanced materials used in electronics and engineering.

2-Fluorotoluene also finds use in the development of liquid crystal materials. The fluorine atom's presence can alter the alignment and optical properties of liquid crystals, which are essential in the production of display technologies. By tuning the properties of these materials, 2-fluorotoluene contributes to the advancement of high-performance displays and other optical devices.

Despite its versatile applications, the use of 2-fluorotoluene must be managed carefully due to environmental and health considerations. The presence of fluorine in organic compounds can lead to persistent environmental pollutants if not handled properly. As such, ongoing research aims to improve the safety and environmental impact of fluorinated chemicals while maintaining their beneficial properties.

References

2023. Hydrothermal defluorination of fluorobenzene in the presence of sodium hydroxide. Journal of Material Cycles and Waste Management, 25(5).
DOI: 10.1007/s10163-023-01741-5

2022. Aerobic Photooxidation of Toluene Derivatives into Carboxylic Acids with Bromine-Water under Catalyst-Free Conditions. Synlett, 33(16).
DOI: 10.1055/a-1887-7885

2017. Palladium-Catalyzed Decarboxylation of Benzyl Fluorobenzoates. Synlett, 28(16).
DOI: 10.1055/s-0036-1588572