Benzyl chloride is a chemical compound used in various industries. It is derived from benzene and has applications in pharmaceuticals, dyes, and perfumes.
| IUPAC Name | Benzyl Chloride |
| Molecular Formula | C₇H₇Cl |
| CAS Number | 100-44-7 |
| Synonyms | α-Chlorotoluene, Benzylchlorid, Chloromethylbenzene, Phenylmethyl chloride |
| InChI | InChI=1S/C7H7Cl/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 |
Benzyl Chloride Properties
Benzyl Chloride Formula
The chemical formula of benzylchlorid is C7H7Cl or C6H5CH2Cl. It consists of seven carbon atoms, seven hydrogen atoms, and one chlorine atom. The formula represents the arrangement of these atoms in the molecule, providing valuable information about its composition.
Benzyl Chloride Molar Mass
The molar mass of benzylchlorid is calculated by adding up the atomic masses of its constituent elements. In this case, carbon has a molar mass of 12.01 g/mol, hydrogen has a molar mass of 1.01 g/mol, and chlorine has a molar mass of 35.45 g/mol. Adding them together, the molar mass of benzylchlorid is approximately 126.58 g/mol.
Benzyl Chloride Boiling Point
Benzylchlorid has a boiling point of approximately 179 °C (354 °F). This temperature indicates the point at which the liquid state of benzylchlorid changes into a gaseous state under standard atmospheric pressure. It is an important parameter to consider when handling and processing this compound.
Benzyl Chloride Melting Point
The melting point of benzylchlorid is around -39 °C (-38 °F). This is the temperature at which the solid form of benzylchlorid transforms into a liquid state. Knowledge of the melting point is essential for proper storage and handling of the compound.
Benzyl Chloride Density g/mL
Benzylchlorid has a density of approximately 1.10 g/mL. Density refers to the mass of a substance per unit volume. This value helps determine the amount of benzylchlorid present in a given volume and is important for various applications and calculations.
Benzyl Chloride Molecular Weight
The molecular weight of benzylchlorid is calculated by summing up the atomic weights of its constituent atoms. With carbon having a weight of 12.01 g/mol, hydrogen 1.01 g/mol, and chlorine 35.45 g/mol, the molecular weight of benzylchlorid is approximately 126.58 g/mol.
Benzyl Chloride Structure
Benzylchlorid has a molecular structure consisting of a benzene ring (a six-carbon aromatic ring) with a chlorine atom attached to one of the carbon atoms in the ring. This structure is known as an aryl halide and plays a crucial role in its reactivity and chemical properties.
Benzyl Chloride Solubility
Benzylchlorid is sparingly soluble in water. It exhibits better solubility in organic solvents like ethanol and ether. This limited solubility in water and high solubility in organic solvents influences its applications and methods of handling and purification.
| Appearance | Colorless to pale yellow liquid |
| Specific Gravity | 1.104 g/mL |
| Color | Colorless to pale yellow |
| Odor | Pungent, sweet, almond-like |
| Molar Mass | 126.58 g/mol |
| Density | 1.10 g/mL |
| Melting Point | -39 °C (-38 °F) |
| Boiling Point | 179 °C (354 °F) |
| Flash Point | 65 °C (149 °F) |
| Water Solubility | Slightly soluble |
| Solubility | Soluble in organic solvents |
| Vapor Pressure | 4.9 mmHg at 25 °C |
| Vapor Density | 4.36 (air = 1) |
| pKa | 7.08 |
| pH | Approximately 7 |
Benzyl Chloride Safety and Hazards
Benzylchlorid poses potential safety hazards and should be handled with caution. It is considered toxic and can cause severe irritation to the eyes, skin, and respiratory system. Inhalation or ingestion can lead to respiratory distress and damage to internal organs. Direct contact with the skin may result in burns and dermatitis. Benzylchlorid is also flammable, and its vapors can form explosive mixtures with air. Adequate ventilation, personal protective equipment, and proper storage and handling procedures are essential to minimize risks. In case of exposure, immediate medical attention is necessary. It is crucial to follow safety guidelines and consult safety data sheets when working with benzylchlorid.
| Hazard Symbols | Skull and crossbones |
| Safety Description | Highly toxic by inhalation and ingestion. Causes severe skin burns and eye damage. Flammable liquid and vapor. |
| UN IDs | UN 1738 |
| HS Code | 2903.39.10 |
| Hazard Class | 6.1 (Toxic substances) |
| Packing Group | II (Intermediate) |
| Toxicity | Acute oral toxicity – High |
Benzyl Chloride Synthesis Methods
Different methods can synthesize benzylchlorid.
One common method involves the reaction between benzyl alcohol and hydrochloric acid. In this process, hydrochloric acid acts as a reagent, facilitating the substitution of the hydroxyl group (-OH) in benzyl alcohol with a chlorine atom. The reaction typically involves applying heat and continuously boiling the reaction mixture under reflux conditions.
Another method involves the reaction between benzyl alcohol and thionyl chloride. Thionyl chloride serves as both a reactant and a solvent in this process. The reaction utilizes an S[sub]N[/sub]2 mechanism, where thionyl chloride displaces the hydroxyl group of benzyl alcohol with a chlorine atom.
To synthesize benzylchlorid, one can perform the chlorination of toluene by using chlorine gas or other chlorinating agents. The presence of a catalyst, such as ferric chloride or aluminum chloride, initiates the reaction and facilitates the substitution of a hydrogen atom in the methyl group of toluene with a chlorine atom.
These synthesis methods allow for the production of benzylchlorid on a commercial scale, providing a versatile precursor for various organic compounds and applications. It is important to note that safety precautions and appropriate equipment should be utilized when working with these chemicals and reactions.
Benzyl Chloride Uses
Benzylchlorid finds numerous applications across various industries due to its versatile nature and reactivity. Here are some key uses of benzylchlorid:
- Pharmaceutical Industry: The pharmaceutical industry utilizes benzylchlorid as a valuable intermediate to synthesize pharmaceutical compounds, including antibiotics, antihistamines, and sedatives.
- Chemical Manufacturing: In chemical manufacturing, benzylchlorid plays a crucial role in producing dyes, perfumes, and flavoring agents, imparting unique aromatic characteristics to these products.
- Agrochemicals: Benzylchlorid actively contributes to the agricultural industry’s efforts in protecting crops from pests and diseases as it actively participates in the synthesis of pesticides and herbicides.
- Polymer Industry: The polymer industry uses benzylchlorid in the production of polymers such as polystyrene, which finds applications in various consumer goods and packaging materials.
- Solvent: Benzylchlorid acts as a solvent for cellulose, resins, and other organic compounds, finding applications in paint strippers and adhesive formulations.
- Chemical Reagent: Benzylchlorid serves as a reagent for various organic transformations, enabling the introduction of the benzyl functional group in chemical synthesis.
- Rubber Industry: The rubber industry employs benzylchlorid in the vulcanization process of rubber, enhancing its durability and strength.
- Research and Development: Benzylchlorid serves as a versatile compound in laboratories for exploring various chemical reactions and developing new molecules.
- Textile Industry: The textile industry utilizes benzylchlorid in the production of textile auxiliaries and dyeing processes.
- Surfactant Manufacturing: Benzylchlorid actively plays a role in the synthesis of surfactants utilized in cleaning agents, detergents, and personal care products.
These diverse applications highlight the significance of benzylchlorid in several industries, contributing to the development of numerous products and advancements in various fields.
Questions:
Q: What is the IUPAC name of benzyl chloride?
A: The IUPAC name of benzylchlorid is chloromethylbenzene.
Q: How can benzyl chloride be prepared from toluene?
A: Benzylchlorid can be prepared from toluene by chlorination using chlorine gas or other chlorinating agents in the presence of a catalyst.
Q: Which is more electrophilic, benzoyl chloride or benzyl chloride?
A: Benzoyl chloride is more electrophilic than benzylchlorid due to the presence of the electron-withdrawing carbonyl group.
Q: Is benzyl chloride a primary alkyl halide?
A: Yes, benzylchlorid is a primary alkyl halide since the chlorine atom is attached to a carbon atom directly bonded to the aromatic ring.
Q: What does benzyl chloride do?
A: Benzylchlorid is a versatile compound used as an intermediate in the synthesis of pharmaceuticals, dyes, perfumes, and other organic compounds.
Q: Can you test blood for benzyl chloride?
A: Yes, blood tests can detect the presence of benzylchlorid, providing information about exposure or potential toxicity.
Q: Is benzylchlorid soluble?
A: Yes, benzylchlorid is soluble in water and many organic solvents.
Q: Is benzylchlorid toxic?
A: Benzyl alcohol can be toxic if ingested or used in high concentrations, potentially causing adverse effects on the central nervous system.
Q: Is benzylchlorid flammable?
A: Yes, benzylchlorid is flammable and should be handled with caution near open flames or ignition sources.