Benzoyl chloride is a chemical compound used in various industries. It reacts with other substances to form derivatives such as benzoyl peroxide, a common ingredient in acne treatments.
| IUPAC Name | Benzoyl Chloride |
| Molecular Formula | C7H5ClO |
| CAS Number | 98-88-4 |
| Synonyms | Benzoic acid, chloride, Benzenecarbonyl chloride, Phenylcarbonyl chloride |
| InChI | InChI=1S/C7H5ClO/c8-6-7(9)4-2-1-3-5-7/h1-5H |
Benzoyl Chloride Properties
Benzoyl Chloride Formula
The formula of benzoylchloride is C7H5ClO. It represents the arrangement of carbon, hydrogen, chlorine, and oxygen atoms in the compound. The formula provides valuable information about the elemental composition and structural makeup of benzoylchloride.
Benzoyl Chloride Molar Mass
The molar mass of benzoylchloride is calculated by summing 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, chlorine has a molar mass of 35.45 g/mol, and oxygen has a molar mass of 16.00 g/mol. By adding up these values, the molar mass of benzoylchloride is found to be approximately 140.57 g/mol.
Benzoyl Chloride Boiling Point
Benzoylchloride has a boiling point of around 197-198°C. This is the temperature at which the liquid compound changes into a gaseous state under standard atmospheric pressure. The boiling point provides insight into the volatility and vaporization characteristics of benzoylchloride.
Benzoyl Chloride Melting Point
The melting point of benzoylchloride is around -1°C. It signifies the temperature at which the solid form of benzoylchloride transforms into a liquid state. The melting point is indicative of the compound’s physical properties and its ability to transition between different phases.
Benzoyl Chloride Density g/mL
Benzoylchloride has a density of approximately 1.21 g/mL. Density refers to the mass of a substance per unit volume. This property provides information about the compactness or concentration of benzoylchloride in a given volume.
Benzoyl Chloride Molecular Weight
The molecular weight of benzoylchloride is calculated by summing up the atomic weights of all the atoms in a molecule. In this case, the molecular weight of benzoylchloride is approximately 140.57 g/mol. It is an essential parameter used in stoichiometric calculations and determining the quantity of benzoylchloride in chemical reactions.
Benzoyl Chloride Structure
The structure of benzoylchloride consists of a benzene ring attached to a carbonyl group (-C=O) and a chlorine atom (-Cl) directly bonded to the carbon atom of the carbonyl group. This arrangement can be represented as PhCOCl, where “Ph” represents the benzene ring. The structure showcases the connectivity and bonding of atoms in benzoylchloride.
Benzoyl Chloride Solubility
Benzoylchloride is sparingly soluble in water. It exhibits a higher solubility in organic solvents such as acetone, ether, and benzene. The solubility characteristics of benzoylchloride influence its applications and interactions with other substances in various chemical processes.
| Appearance | Colorless to pale yellow liquid |
| Specific Gravity | 1.21 g/mL |
| Color | Colorless to pale yellow |
| Odor | Irritating, pungent odor |
| Molar Mass | 140.57 g/mol |
| Density | 1.21 g/mL |
| Melting Point | -1°C |
| Boiling Point | 197-198°C |
| Flash Point | 77°C |
| Water Solubility | Reacts |
| Solubility | Soluble in organic solvents such as acetone, ether, and benzene |
| Vapour Pressure | 4.95 mmHg at 25°C |
| Vapour Density | 5.3 |
| pKa | 4.18 |
| pH | Not applicable (acidic when dissolved in water) |
Benzoyl Chloride Safety and Hazards
Benzoylchloride poses certain safety hazards and should be handled with caution. It is highly irritating to the skin, eyes, and respiratory system, causing burns and severe discomfort upon contact. Inhalation of its vapors can lead to respiratory tract irritation and lung damage. It is essential to use appropriate protective equipment such as gloves, goggles, and a respirator when working with benzoylchloride. The compound is flammable and may ignite upon exposure to heat or flames, releasing toxic fumes. Furthermore, it reacts violently with water, alcohols, and bases, potentially resulting in fires or explosions. Proper storage, handling, and disposal procedures should be followed to minimize risks.
| Hazard Symbols | Corrosive, Toxic |
| Safety Description | Avoid contact with skin and eyes. Use in a well-ventilated area. Handle with appropriate protective equipment. |
| UN IDs | UN 1736 |
| HS Code | 2916.31.00 |
| Hazard Class | 8 (Corrosive), 6.1 (Toxic) |
| Packing Group | II (Intermediate) |
| Toxicity | Highly toxic and corrosive. |
Benzoyl Chloride Synthesis Methods
There are several methods for synthesizing benzoylchloride. One common approach is the oxidation of benzaldehyde using a suitable oxidizing agent, such as chlorine gas or phosphorus pentachloride (PCl5). In this method, you mix benzaldehyde with the oxidizing agent under controlled conditions, and it produces benzoylchloride.
Another method involves the reaction between benzoyl peroxide and hydrogen chloride gas. The benzoyl peroxide acts as a radical initiator, promoting the reaction with hydrogen chloride to yield benzoylchloride.
To prepare benzoylchloride, one can treat benzoic acid with either thionyl chloride (SOCl2) or phosphorus trichloride (PCl3) under reflux conditions. The reaction produces an acid chloride as an intermediate, which subsequently converts into benzoylchloride.
Additionally, the reaction of benzotrichloride with carbon monoxide (CO) in the presence of a catalyst, such as copper, can also lead to the synthesis of benzoylchloride.
It is important to note that these methods should be carried out in a well-ventilated area with proper safety precautions, as benzoylchloride is a hazardous compound. Careful handling and adherence to proper lab protocols are necessary to ensure a safe synthesis process.
Benzoyl Chloride Uses
Benzoylchloride has various uses across different industries due to its versatile chemical properties. Here are some notable applications:
- Pharmaceutical Industry: The pharmaceutical industry uses benzoylchloride as a key intermediate to synthesize pharmaceutical compounds, including analgesics, antiseptics, and antihistamines.
- Polymer Industry: In the polymer industry, benzoylchloride acts as a monomer, contributing to the structural stability and thermal resistance of polymers such as polycarbonates, polyamides, and polyesters.
- Organic Synthesis: Benzoylchloride serves as a reagent in acylation reactions, facilitating the introduction of the benzoyl group into organic molecules.
- Agrochemicals: Benzoylchloride plays a crucial role in crop protection and pest control by contributing to the synthesis of herbicides and insecticides.
- Dye Manufacturing: Benzoylchloride is a precursor for producing various dyes and pigments, which are essential for coloring textiles, plastics, and printing inks.
- Perfume and Fragrance Industry: The fragrance and perfume industry utilize benzoylchloride to synthesize fragrances and perfume compounds, enhancing their aromatic characteristics.
- Chemical Research: Research laboratories apply benzoylchloride in the synthesis of new chemical compounds, contributing to the development of innovative materials and pharmaceuticals.
- Rubber Industry: The rubber industry employs benzoylchloride as a crosslinking agent to modify rubber properties, improving its durability and strength.
- Adhesive Manufacturing: Manufacturers use benzoylchloride to produce adhesives and sealants, enhancing bonding properties.
- Textile Industry: In the textile industry, benzoylchloride acts as a catalyst and stabilizer during the manufacture of synthetic fibers such as nylon, polyester, and spandex, ensuring their quality and performance.
These diverse applications demonstrate the significance of benzoylchloride in various industrial sectors.
Questions:
Q: Which of the following reagents convert(s) benzoyl chloride to phenyl propyl ketone?
A: The reagent that converts benzoylchloride to phenyl propyl ketone is a Grignard reagent of phenylmagnesium bromide (PhMgBr), followed by reaction with propyl halide.
Q: What product would be formed from the reaction of benzoyl chloride with 4-chlorophenol?
A: The product formed from the reaction of benzoyl chloride with 4-chlorophenol is 4-chlorobenzoyl phenol.
Q: How to find the yield of ammonolysis of benzoyl chloride?
A: The yield of ammonolysis of benzoylchloride can be determined by dividing the amount of the desired product obtained by the theoretical yield, and multiplying by 100 to express it as a percentage.
Q: Is benzoyl chloride or benzyl chloride more electrophilic?
A: Benzoylchloride is more electrophilic than benzyl chloride due to the presence of the highly electron-withdrawing carbonyl group.
Q: Which of the following reagents is used in the following reaction? benzoic acid to benzoyl chloride, hydrolysis of benzoyl chloride?
A: The reagent used in the conversion of benzoic acid to benzoylchloride is thionyl chloride (SOCl2), and for the hydrolysis of benzoylchloride, it is water or an aqueous base.
Q: What are the products formed when benzoyl chloride reacts with cyclohexanol?
A: The products formed from the reaction of benzoylchloride with cyclohexanol are cyclohexyl benzoate and hydrogen chloride (HCl).
Q: How to dry benzoyl chloride?
A: Benzoylchloride can be dried by adding a suitable drying agent such as anhydrous calcium chloride or anhydrous magnesium sulfate, followed by filtration.
Q: Which is more electrophilic, benzoyl chloride or benzyl chloride?
A: Benzoylchloride is more electrophilic than benzyl chloride due to the presence of the carbonyl group, which withdraws electron density and increases electrophilicity.
Q: Is benzoyl chloride water-soluble?
A: No, benzoylchloride is not water-soluble. It reacts with water to form benzoic acid and hydrochloric acid.