Benzil or C14H10O2 is a yellow crystalline organic compound used as a precursor in dye synthesis and as a photoinitiator in polymer chemistry. It can also act as a reducing agent and is an intermediate in benzilic acid formation.
| IUPAC Name | 1,2-diphenyl-1,2-dicarboxyethylene |
| Molecular Formula | C14H10O2 |
| CAS Number | 134-81-6 |
| Synonyms | 1,2-Diphenyl-1,2-propanedione, 1,2-Diphenylethanedione, Benzilum, Benzil |
| InChI | InChI=1S/C14H10O2/c15-13(14(16)17)11-6-8-12(9-7-11)10-5-3-1-2-4-6/h1-9H,10-17H2 |
Benzil Molecular Weight
The molecular weight of benzil is 210.24 g/mol. It is the sum of the atomic masses of all the atoms in a molecule of benzil. The molecular weight of benzil is calculated based on its molecular formula, C14H10O2.
Benzil Density g/mL
The density of benzil is 1.20 g/mL. It is the measure of mass per unit volume of a substance. The density of benzil is relatively low, which makes it easier to handle compared to some other substances with higher density.
Benzil Boiling Point
The boiling point of benzil is 350°C (662°F). It is the temperature at which the vapor pressure of a liquid is equal to the atmospheric pressure and the liquid changes into a vapor. The boiling point of a substance depends on various factors such as pressure, molecular weight, and intermolecular forces.
Benzil Melting Point
The melting point of benzil is 98°C (270°F). It is the temperature at which a solid changes into a liquid. The melting point of benzil is relatively low, which makes it a useful intermediate in organic syntheses.
Benzil Molar Mass
The molar mass of C14H10O2 is 210.24 g/mol. It is the amount of substance that contains the same number of entities (e.g. atoms, molecules, ions) as the number of entities in 12 grams of pure carbon-12. The molar mass of benzil is calculated based on its molecular formula, C14H10O2.
Benzil Structure
Benzil is a yellow crystalline organic compound that has a molecular formula of C14H10O2. It is a diketone that consists of two phenyl groups attached to a central carbon-carbon double bond. The molecule is planar, and the double bond is planar. The benzil molecule has a characteristic strong yellow color that makes it useful as a reference compound in analytical chemistry.
Benzil Formula
The chemical formula of benzil is C14H10O2. It represents the constituent elements of benzil and their relative ratios. The formula shows that benzil consists of 14 carbon atoms, 12 hydrogen atoms, and 2 oxygen atoms.
Benzil NMR
C14H10O2 can be analyzed using Nuclear Magnetic Resonance (NMR) spectroscopy. NMR spectroscopy is a powerful tool that provides information on the chemical structure and interactions of molecules. In NMR spectroscopy, the magnetic properties of the nucleus are used to determine the chemical environment of the nucleus and to obtain information on the bonding and chemical shifts of the molecule. The NMR spectrum of C14H10O2 provides information on the number of protons in the molecule and the chemical environment of each proton, which helps to confirm the structure of C14H10O2.
| Appearance | Yellow crystalline solid |
| Specific Gravity | 1.20 g/mL |
| Color | Yellow |
| Odor | Odorless |
| Molar Mass | 210.24 g/mol |
| Density | 1.20 g/mL |
| Melting Point | 94.8°C |
| Boiling Point | 350°C (662°F) |
| Flash Point | Not available |
| Water Solubility | Slightly soluble in water |
| Solubility | Soluble in ethanol and ether |
| Vapor Pressure | Not available |
| Vapor Density | Not available |
| pKa | Not available |
| pH | Not available |
Benzil Safety and Hazards
C14H10O2 is considered to be a moderately toxic substance and should be handled with care. It is highly flammable and should be stored away from heat sources and sparks. Inhalation of C14H10O2 vapors may cause irritation to the eyes, nose, and throat, and can also cause respiratory problems. Skin contact with C14H10O2 may cause skin irritation and redness. Ingestion of C14H10O2 can cause stomach irritation and digestive problems. If ingested in large amounts, it can lead to more serious health problems such as vomiting, dizziness, and unconsciousness. It is important to wear protective gloves and eye protection when handling C14H10O2 and to work in a well-ventilated area to minimize exposure. If any adverse effects occur after contact with C14H10O2, it is recommended to seek immediate medical attention.
| Hazard Symbols | Flammable |
| Safety Description | S24/25 – Avoid contact with skin and eyes |
| UN IDs | UN2024 – Dangerous goods, Hazard Class 3 |
| HS Code | 2915.90.90 |
| Hazard Class | 3 – Flammable liquids |
| Packing Group | III – Moderate hazard |
| Toxicity | Moderately toxic |
Benzil Synthesis Methods
C14H10O2 can be synthesized through various methods, including the following:
- Oxidation of Diphenylmethanol: Diphenylmethanol is oxidized using chromium trioxide to form C14H10O2. This is a common method used in the synthesis of C14H10O2 as it is simple and cost-effective.
- Wacker oxidation: This method involves the use of a palladium catalyst and a hydroperoxide oxidant to convert the alkene to C14H10O2. The reaction is typically carried out in the presence of a solvent, such as ethanol or water.
- Knoevenagel condensation: In this method, C14H10O2 is synthesized through a reaction between benzaldehyde and barbituric acid in the presence of a strong base such as sodium hydroxide or potassium hydroxide.
- Ullmann reaction: This method involves the coupling of two aromatic compounds through a copper-catalyzed reaction. In the synthesis of C14H10O2, two molecules of benzaldehyde are reacted to form C14H10O2.
- Baeyer-Villiger oxidation: In this method, C14H10O2 is synthesized by oxidizing cyclohexanone to C14H10O2 in the presence of a peroxyacid oxidant and a catalytic amount of a tertiary amine.
The choice of synthesis method for C14H10O2 depends on various factors, including the availability of starting materials, the desired yield and purity of the product, and the cost and time involved in the synthesis process.
Benzil Uses
C14H10O2 is a versatile chemical that has a number of uses in various fields. Some of the common uses of C14H10O2 are:
- Fine Chemical Production uses C14H10O2 as a starting material in the production of various fine chemicals including antioxidants, flame retardants, and dyes.
- Polymer Synthesis employs C14H10O2 in the synthesis of polymers including polycarbonates and polyurethanes with a wide range of applications in various industries.
- Pesticides utilize C14H10O2 as an intermediate in the synthesis of certain pesticides for controlling pests in crops and gardens.
- Cosmetics utilize C14H10O2 as a fragrance in certain cosmetic products such as perfumes and colognes to provide a fresh, floral aroma.
- The flavor and fragrance industry employs C14H10O2 as a flavor and fragrance ingredient to impart a woody, floral aroma to food and cosmetic products.
In conclusion, C14H10O2 is a versatile chemical that has a wide range of uses in various industries, including the fine chemical, pharmaceutical, and cosmetic industries.
Questions:
Is benzil polar?
Yes, C14H10O2 is polar. It has a polar molecular structure due to the presence of polar functional groups, such as carbonyl (-C=O) and phenyl (-C6H5) groups. This polar structure makes C14H10O2 soluble in polar solvents, such as water and alcohols, but insoluble in non-polar solvents, such as hydrocarbons. The polar nature of C14H10O2 also allows it to participate in various polar reactions, such as hydrogen bonding and dipole-dipole interactions.
What type of reaction is the formation of benzilic acid fall under?
The formation of C14H10O2ic acid from C14H10O2 is a type of rearrangement reaction known as the benzilic acid rearrangement. This reaction is a rearrangement of the carbonyl group in C14H10O2 to form a new carboxylic acid functional group in benzilic acid. The benzilic acid rearrangement is an example of a Beckmann rearrangement, which is a type of nucleophilic substitution reaction that involves the rearrangement of cyclic ketones to amides or carboxylic acids. The reaction mechanism involves the formation of a cyclic intermediate, followed by the migration of the carbonyl group and the elimination of a leaving group.