Ethyl 4-aminobenzoate, also known as benzocaine, is a local anesthetic commonly used in dental procedures and topical pain relief products. It works by blocking nerve signals.
| IUPAC Name | Ethyl 4-aminobenzoate |
| Molecular Formula | C9H11NO2 |
| CAS Number | 94-09-7 |
| Synonyms | Benzocaine, p-aminobenzoic acid ethyl ester, ethyl aminobenzoate, ethyl p-aminobenzoate, 4-(ethoxycarbonyl)anilinium benzoate |
| InChI | InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3 |
Ethyl 4-aminobenzoate molar mass:
The molar mass of Ethyl 4-aminobenzoate is 165.19 g/mol. Molar mass is the mass of one mole of a substance and is calculated by summing the atomic masses of all the atoms in a molecule. The molar mass is an important parameter in chemical reactions and is used to determine the amount of substance present in a sample.
Ethyl 4-aminobenzoate boiling point:
The boiling point of Ethyl 4-aminobenzoate is 310.7 °C. The boiling point is the temperature at which the vapor pressure of a liquid equals the external pressure. At the boiling point, a substance undergoes a phase transition from liquid to gas. The high boiling point of Ethyl 4-aminobenzoate makes it a suitable compound for use in dental and medical procedures where high temperatures are involved.
Ethyl 4-aminobenzoate melting point:
The melting point of Ethyl 4-aminobenzoate is 89-92 °C. The melting point is the temperature at which a solid substance changes to a liquid state. The melting point of a compound depends on its chemical structure, purity, and pressure. Ethyl 4-aminobenzoate has a low melting point, which makes it easy to handle and use in the preparation of topical anesthetics and pain relievers.
Ethyl 4-aminobenzoate density g/ml:
The density of Ethyl 4-aminobenzoate is 1.17 g/mL. Density is the amount of mass per unit volume of a substance. The density of a compound depends on its molecular weight, temperature, and pressure. The high density of Ethyl 4-aminobenzoate makes it a heavy compound, which can be easily measured and used in precise quantities in chemical reactions.
Benzocaine molecular weight:
The molecular weight of Benzocaine is 165.19 g/mol. Molecular weight is the sum of the atomic weights of all the atoms in a molecule. The molecular weight of a compound is important in determining its physical and chemical properties.
Benzocaine structure:
The structure of Benzocaine is a white crystalline powder with a chemical formula of C9H11NO2. It has a benzene ring with a carboxyl group and an amino group attached to it. The ethyl group is attached to the amino group, which makes it a derivative of benzoic acid. The structure of Benzocaine is important in understanding its physical and chemical properties.
Benzocaine formula:
The chemical formula for Benzocaine is C9H11NO2. It is a derivative of benzoic acid and has an ethyl group attached to the amino group. The formula of Benzocaine is used to represent the composition of the compound and is important in understanding its physical and chemical properties.
| Appearance | White crystalline powder |
| Specific Gravity | 1.17 g/mL |
| Color | Colorless to white |
| Odor | Odorless |
| Molar Mass | 165.19 g/mol |
| Density | 1.17 g/mL |
| Melting Point | 89-92 °C |
| Boiling Point | 310.7 °C |
| Flash Point | 164.2 °C |
| Water Solubility | Slightly soluble |
| Solubility | Soluble in ethanol, chloroform, ether |
| Vapour Pressure | 1.07E-07 mmHg at 25°C |
| Vapour Density | 5.7 (vs air) |
| pKa | 2.5 |
| pH | 6.5 – 7.5 |
Ethyl 4-aminobenzoate Safety and Hazards
Benzocaine can cause skin and eye irritation upon contact. Ingestion or inhalation of the compound may cause irritation to the digestive or respiratory systems. Long-term or repeated exposure to Benzocaine may cause damage to the liver or kidneys. The compound is not considered to be carcinogenic or mutagenic, but caution should be exercised when handling it. Proper personal protective equipment should be worn, such as gloves and safety glasses, when handling Benzocaine. In case of accidental ingestion or exposure, seek medical attention immediately. Benzocaine should be stored in a cool, dry place and away from sources of ignition or heat.
| Hazard Symbols | Xi |
| Safety Description | S22-S24/25-S36-S37 |
| UN IDs | Not regulated |
| HS Code | 29224990 |
| Hazard Class | Irritant |
| Packing Group | Not regulated |
| Toxicity | LD50 (rat, oral) = 940 mg/kg; LD50 (rat, dermal) > 2 g/kg |
Ethyl 4-aminobenzoate Synthesis Methods
Benzocaine, also known as benzocaine, can be synthesized using various methods. One common method involves the reaction of p-aminobenzoic acid with ethanol in the presence of a strong acid catalyst, such as sulfuric acid or hydrochloric acid. The resulting ethyl ester of p-aminobenzoic acid is then treated with sodium nitrite and hydrochloric acid to form the diazonium salt. This salt is then reacted with sodium acetate and acetic anhydride to yield ethyl 4-acetoxy-3-nitrobenzoate, which is subsequently reduced with tin and hydrochloric acid to produce Benzocaine.
Another method involves the reaction of p-nitroaniline with ethyl chloroformate in the presence of sodium hydroxide to form ethyl p-nitrophenylcarbamate. This compound is then reduced with hydrogen gas and palladium catalyst to yield benzocaine.
In a third method, ethyl 4-nitrobenzoate is reduced with zinc dust and hydrochloric acid to produce Benzocaine.
Regardless of the synthesis method used, the resulting compound must be purified through recrystallization or other methods to obtain a pure product. Benzocaine is a commonly used local anesthetic and is also used in the production of various pharmaceuticals and cosmetics.
Ethyl 4-aminobenzoate Uses
Benzocaine, a common local anesthetic, numbs the affected area and provides temporary relief from pain and itching caused by minor skin irritations, sore throat, toothache, and teething. It is available in various forms, such as creams, gels, sprays, and lozenges, and is widely used in pharmaceuticals and cosmetic products. It is a common ingredient in cough drops, throat sprays, oral analgesic gels, sunscreen lotions, and lip balms to relieve pain caused by sunburn and chapped lips.
The food industry also uses Benzocaine as a flavoring agent in candies, chewing gum, and other confectionery products to provide a cooling and numbing effect. The US Food and Drug Administration (FDA) approves it for use in food products.
However, benzocaine should only be used as directed by a healthcare professional or specified on the product label to avoid adverse side effects such as skin irritation and allergic reactions. Therefore, it is essential to use it with caution.
Questions:
Is ethyl 4-aminobenzoate polar?
Yes, Ethyl 4-aminobenzoate is polar. It has a polar functional group (the amino group) and a polar ester group, which gives it a net dipole moment. This means that it has a partial positive charge on one end of the molecule and a partial negative charge on the other end, making it polar. This property of benzocaine makes it soluble in polar solvents, such as water and ethanol, and less soluble in non-polar solvents, such as hexane and benzene. The polarity of Ethyl 4-aminobenzoate also affects its physical and chemical properties, such as its melting point, boiling point, and solubility.
Is ethyl 4-aminobenzoate soluble in water?
Yes, Ethyl 4-aminobenzoate is partially soluble in water. It has a polar functional group and an ester group, which makes it capable of forming hydrogen bonds with water molecules. However, its solubility in water is limited due to the non-polar ethyl group present in its structure. This means that Ethyl 4-aminobenzoate is more soluble in organic solvents, such as ethanol and acetone, than in water. The solubility of Ethyl 4-aminobenzoate in water also depends on various factors, such as temperature, pH, and the presence of other substances. Under normal conditions, the solubility of Ethyl 4-aminobenzoate in water is approximately 0.3 g/L at 25°C.