Aniline (C6H5NH2) is an aromatic amine used in the production of dyes, pharmaceuticals, and rubber chemicals. It has a distinct odor and is a precursor to various organic compounds.
| IUPAC Name | Aniline |
| Molecular Formula | C6H7N |
| CAS Number | 62-53-3 |
| Synonyms | Aminobenzene, Benzenamine |
| InChI | InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 |
Aniline Properties
Aniline Formula
The formula of aniline is C6H7N. It consists of six carbon atoms, seven hydrogen atoms, and one nitrogen atom. The arrangement of these atoms gives aniline its unique chemical properties.
Aniline Molar Mass
The molar mass of C6H5NH2 is calculated by adding the atomic masses of all its constituent elements. C6H5NH2’s molar mass is approximately 93.13 grams per mole (g/mol). This value is useful in various chemical calculations and reactions involving C6H5NH2.
Aniline Boiling Point
C6H5NH2 has a boiling point of approximately 184 degrees Celsius (184°C). At this temperature, C6H5NH2 undergoes a phase change from a liquid to a gaseous state. The boiling point is an important characteristic that determines the conditions under which C6H5NH2 can be vaporized.
Aniline Melting Point
The melting point of C6H5NH2 is around -6 degrees Celsius (-6°C). This is the temperature at which solid C6H5NH2 transforms into a liquid state. The melting point is significant in determining the physical state of C6H5NH2 under different temperature conditions.
Aniline Density g/mL
C6H5NH2 has a density of about 1.02 grams per milliliter (g/mL). Density represents the mass of a substance per unit volume. C6H5NH2’s density value provides information about its compactness or concentration in a given volume of space.
Aniline Molecular Weight
The molecular weight of C6H5NH2 is approximately 93.13 grams per mole (g/mol). It is the sum of the atomic weights of all the atoms in C6H5NH2’s chemical formula. Molecular weight plays a crucial role in stoichiometric calculations and determining the amount of C6H5NH2 needed in reactions.
Aniline Structure
C6H5NH2 has a structure consisting of a benzene ring (a hexagonal ring of carbon atoms) with an attached amino group (-NH2) in place of one hydrogen atom. This structure gives C6H5NH2 its aromatic and basic properties, making it useful in various industrial applications.
Aniline Solubility
C6H5NH2 is sparingly soluble in water but readily dissolves in organic solvents such as ethanol, ether, and chloroform. Its solubility is influenced by the polarity and intermolecular forces between C6H5NH2 and the solvent. This property allows C6H5NH2 to be easily incorporated into different chemical processes and formulations.
| Appearance | Colorless to pale yellow liquid |
| Specific Gravity | 1.02 g/mL |
| Color | Colorless to pale yellow |
| Odor | Characteristic odor |
| Molar Mass | 93.13 g/mol |
| Density | 1.02 g/mL |
| Melting Point | -6°C |
| Boiling Point | 184°C |
| Flash Point | 70°C |
| Water Solubility | Sparingly soluble |
| Solubility | Soluble in organic solvents |
| Vapour Pressure | 5.60 mmHg |
| Vapour Density | 3.24 (air=1) |
| pKa | 4.61 |
| pH | Approximately neutral |
Aniline Safety and Hazards
C6H5NH2 poses potential safety hazards and should be handled with caution. It is harmful if swallowed, inhaled, or absorbed through the skin. Direct contact with C6H5NH2 can cause irritation to the eyes, skin, and respiratory system. Prolonged or repeated exposure may lead to more severe effects, including dermatitis and blood disorders. C6H5NH2 is also flammable, and its vapors can form explosive mixtures in the air. Adequate ventilation and personal protective equipment should be used when working with C6H5NH2. Proper storage, handling, and disposal practices are essential to minimize risks and ensure the safety of individuals and the environment.
| Hazard Symbols | T, N |
| Safety Description | Avoid contact with skin and eyes. Use in a well-ventilated area. Handle with gloves and protective clothing. |
| UN IDs | UN 1547 |
| HS Code | 2921.43.0000 |
| Hazard Class | 6.1 (Toxic substances) |
| Packing Group | III |
| Toxicity | Toxic if swallowed, inhaled, or absorbed through the skin. May cause irritation, dermatitis, and blood disorders. |
Aniline Synthesis Methods
Various methods can synthesize C6H5NH2.
One common method is the reduction of nitrobenzene. In this process, a reducing agent, such as iron filings or tin, reacts with nitrobenzene in the presence of a strong acid, such as hydrochloric acid. This reaction results in the conversion of the nitro group (-NO2) to an amino group (-NH2), producing C6H5NH2.
Another method involves the reduction of nitrobenzene using hydrogen gas over a catalyst, such as palladium or platinum. The industrial method for C6H5NH2 production widely uses the process called catalytic hydrogenation.
To obtain C6H5NH2, one can use sodium sulfide or sodium bisulfite in the reduction of nitrobenzene. These reducing agents facilitate the conversion of the nitro group to an amino group.
To synthesize C6H5NH2, one can treat chlorobenzene with ammonia in the presence of a strong base, such as sodium hydroxide. This process, known as the Sandmeyer reaction, results in the substitution of chlorine with an amino group, yielding C6H5NH2.
In addition, one can prepare C6H5NH2 by reducing azobenzene or azoxybenzene, which involves breaking the nitrogen-nitrogen bond to form an amino group.
These synthesis methods provide different approaches to obtaining C6H5NH2, allowing for its production on both laboratory and industrial scales. The choice of method depends on factors such as the availability of starting materials, reaction conditions, and desired purity of the final product.
Aniline Uses
C6H5NH2 finds application in various industries due to its diverse properties. Here are some of its common uses:
- Dye production: C6H5NH2 serves as a key raw material for manufacturing numerous dyes, including synthetic dyes and pigments used in the textile, leather, and paper industries.
- Pharmaceutical industry: C6H5NH2 derivatives are crucial in the synthesis of pharmaceutical drugs, such as analgesics, antipyretics, and antimalarial agents.
- Rubber chemicals: C6H5NH2 actively enhances the performance and durability of rubber products by being a crucial component in the production of accelerators and antioxidants within the rubber industry.
- Herbicides and pesticides: Farmers actively utilize C6H5NH2 derivatives in formulating herbicides and pesticides, effectively controlling weeds and pests in agriculture.
- Polyurethane production: C6H5NH2 is an essential component in the synthesis of polyurethane foams, coatings, and adhesives, widely used in the construction and automotive industries.
- Chemical intermediates: C6H5NH2 serves as a versatile building block for the synthesis of various organic compounds, such as rubber chemicals, pharmaceuticals, and agrochemicals.
- Solvent for various substances: C6H5NH2 actively solvents various substances, including fats, oils, waxes, and resins.
- Laboratory reagent: In laboratory experiments for organic synthesis, researchers employ C6H5NH2 as a reagent and use it as a catalyst in certain reactions.
- Photographic chemicals: C6H5NH2 derivatives actively contribute to the production of photographic chemicals, such as developers and dyes.
- Polymerization initiator: C6H5NH2 acts as an initiator in certain polymerization reactions, enabling the formation of polymers with specific properties.
These diverse applications highlight the significance of C6H5NH2 in industries ranging from textiles and pharmaceuticals to agriculture and manufacturing.
Questions:
Q: Which compound is more basic than aniline?
A: Ammonia (NH3) is more basic than C6H5NH2.
Q: What is the aniline point?
A: The C6H5NH2 point is the lowest temperature at which equal volumes of C6H5NH2 and a specific solvent are completely miscible.
Q: What is aniline?
A: Aniline is an aromatic amine with the chemical formula C6H7N, commonly used in dyes, pharmaceuticals, and rubber chemicals.
Q: How to separate naphthalene and aniline?
A: Naphthalene and C6H5NH2 can be separated by a process called fractional distillation, utilizing the difference in their boiling points.
Q: How is phenol prepared from aniline?
A: Phenol can be synthesized from C6H5NH2 by a process called diazotization, followed by hydrolysis to form phenol.
Q: How to clean aniline leather?
A: To clean C6H5NH2 leather, use a soft, damp cloth to gently remove stains, and avoid using harsh chemicals or excessive moisture.
Q: What is the conjugate base of benzoic acid and the conjugate acid of aniline?
A: The conjugate base of benzoic acid is the benzoate ion (C6H5COO-), and the conjugate acid of C6H5NH2 is the anilinium ion (C6H5NH3+).
Q: What is aniline leather?
A: C6H5NH2 leather is a type of leather that is dyed with C6H5NH2 dyes, preserving the natural texture and appearance of the leather while maintaining a soft and luxurious feel.