2-Chloro-6-fluorobenzyl chloride

1. General Information

Chemical Name: 2 - Chloro - 6 - fluorobenzyl chloride

Synonyms: 1 - Chloro - 2 - (chloromethyl)-3 - fluorobenzene; 2,α - Dichloro - 6 - fluorotoluene

CAS Registry Number: 55117 - 15 - 2

Molecular Formula: C₇H₅Cl₂F

Molecular Weight: 179.019 g/mol

2. Physical Properties

Appearance: It is a clear, colorless liquid at room temperature. However, it may have a faint, characteristic odor.

Density: The density is approximately 1.401 g/mL at 25 °C (lit.). This density value indicates that it is heavier than water, which can have implications for its handling and separation in certain processes.

Melting Point: The melting point of 2 - Chloro - 6 - fluorobenzyl chloride is around 7 °C. This relatively low melting point means that it exists as a liquid under normal ambient conditions but can solidify at lower temperatures.

Boiling Point: It boils at 208.5 ± 25.0 °C at 760 mmHg. The boiling point is an important parameter as it helps in determining the conditions for distillation and purification processes.

Solubility: It is insoluble in water. But it shows good solubility in common organic solvents such as ethanol, ether, benzene, and chloroform. This solubility property is crucial for its use in organic synthesis reactions where it can be easily mixed with other organic reactants.

Refractive Index: The refractive index is n20/D 1.537 (lit.). This property can be used to identify and characterize the compound, especially in analytical chemistry techniques.

3. Chemical Properties

Reactivity: The presence of two chlorine atoms and a fluorine atom on the benzene ring makes 2 - Chloro - 6 - fluorobenzyl chloride a highly reactive compound. The chlorine and fluorine atoms are electron - withdrawing groups, which can activate the benzene ring towards nucleophilic substitution reactions. For example, the benzyl chloride moiety is particularly reactive, and the chlorine atom in the - CH₂Cl group can be easily replaced by a variety of nucleophiles such as amines, alcohols, and thiols.

Stability: Under normal storage conditions, it is relatively stable. However, it should be stored away from strong oxidizing agents, bases, and moisture. Contact with moisture can lead to hydrolysis reactions, especially due to the presence of the reactive chlorine atoms. Prolonged exposure to light may also cause some degradation reactions.

4. Applications

Pharmaceutical Industry: It serves as a vital intermediate in the synthesis of various pharmaceutical compounds. For instance, it has been used as an alkylating reagent during the synthesis of 3 - benzylsulfanyl derivatives of 1,2,4 - triazole and 4 - methyl - 1,2,4 - triazole. These triazole derivatives often exhibit interesting biological activities such as antifungal, antibacterial, and anti - inflammatory properties. It is also used in the preparation of 2 - chloro - 6 - fluorobenzylamine, which is required for the synthesis of 9 - substituted adenine. Adenine derivatives are important in the development of drugs for treating various diseases including cancer and viral infections.

Agricultural Chemicals: In the agrochemical field, 2 - Chloro - 6 - fluorobenzyl chloride is used in the production of pesticides, particularly in the synthesis of plant growth regulators. These plant growth regulators can influence various aspects of plant growth and development, such as promoting or inhibiting growth, enhancing fruit set, and improving crop yield and quality.

Specialty Chemicals: It is a fundamental building block for the synthesis of many specialty chemicals. Due to its unique reactivity and structure, it can be incorporated into more complex molecules with specific properties. These specialty chemicals may find applications in areas such as materials science, where they can be used to modify the properties of polymers, or in the formulation of high - performance coatings.

5. Safety Precautions

Toxicity: This compound is toxic. Inhalation, ingestion, or skin contact can cause harm. It can irritate the eyes, skin, and respiratory tract. Prolonged or repeated exposure may lead to more serious health effects. The reactive chlorine and fluorine atoms can react with biological molecules in the body, potentially disrupting normal physiological functions.

Handling: When handling 2 - Chloro - 6 - fluorobenzyl chloride, appropriate personal protective equipment (PPE) should be worn. This includes faceshields, gloves, goggles, and a type ABEK (EN14387) respirator filter. All operations should be carried out in a well - ventilated area, preferably under a fume hood to minimize the risk of inhalation of its vapors.

Storage: Store it in a cool, dry place, away from sources of heat, ignition, and incompatible substances. The storage container should be tightly sealed to prevent leakage. It is recommended to store it in a corrosion - resistant container due to its potential corrosive nature.

6. Packaging and Storage

Packaging: It is typically available in various packaging sizes depending on the quantity required. Common packaging options include glass bottles for laboratory - scale quantities and larger metal or plastic drums for industrial applications. The packaging material should be resistant to the corrosive and reactive nature of the compound.

Shelf Life: Under proper storage conditions (cool, dry, and protected from light and moisture), the shelf life of 2 - Chloro - 6 - fluorobenzyl chloride is usually several months to a year. However, regular quality checks may be necessary to ensure its integrity, especially if it is stored for an extended period.