A chloro 2 6 dimethylacetanilide takes center stage in this captivating exploration, inviting readers to delve into a realm of chemistry that is both intricate and captivating. From its molecular makeup to its diverse applications, this compound unveils a story that is rich in scientific detail and practical relevance.

Within this narrative, we will dissect the chemical structure of a chloro 2 6 dimethylacetanilide, unraveling its IUPAC name, molecular formula, and molar mass. We will delve into its physical and chemical properties, examining its physical state, color, odor, melting point, boiling point, and density.

Its solubility in various solvents and its chemical reactivity will also be brought to light.

Nomenclature and Chemical Structure

Chloro 2 6 dimethylacetanilide is an organic compound with the molecular formula C ₉H ₁₂ClNO. It is a white or off-white solid with a melting point of 104-106 °C. Chloro 2 6 dimethylacetanilide is a derivative of acetanilide, which is a common analgesic and antipyretic drug.

IUPAC Name

The IUPAC name for chloro 2 6 dimethylacetanilide is 2,6-dimethyl-N-(2-chlorophenyl)acetamide.

Common Name

The common name for chloro 2 6 dimethylacetanilide is 2,6-xylidine.

Molecular Formula and Molar Mass

The molecular formula for chloro 2 6 dimethylacetanilide is C ₉H ₁₂ClNO. Its molar mass is 181.65 g/mol.

Physical and Chemical Properties

Chloro 2 6 dimethylacetanilide, also known as Chloro DMAA, is a synthetic chemical compound with the molecular formula C ₉H ₁₂ClNO. It is commonly used as an intermediate in the production of other chemicals and pharmaceuticals.

In its pure form, Chloro DMAA appears as a white or off-white crystalline powder. It is odorless and has a slightly bitter taste. The compound has a melting point of 178-180 °C and a boiling point of 340-342 °C. Its density is approximately 1.2 g/cm ³.

Solubility

Chloro DMAA is moderately soluble in water, with a solubility of about 0.5 g/100 mL at 25 °C. It is more soluble in organic solvents such as ethanol, methanol, and chloroform.

Chemical Reactivity and Stability

Chloro DMAA is a relatively stable compound. It is not easily oxidized or reduced and is resistant to hydrolysis. However, it can react with strong acids and bases to form salts.

Synthesis and Production

Chloro 2 6 dimethylacetanilide can be synthesized through various methods, including:

Friedel-Crafts Acylation

This method involves the reaction of 2,6-dimethylaniline with acetyl chloride in the presence of a Lewis acid catalyst, such as aluminum chloride (AlCl3). The reaction proceeds via electrophilic aromatic substitution, leading to the formation of chloro 2 6 dimethylacetanilide.

Reductive Amination

In this method, 2,6-dimethylaniline is reacted with formaldehyde and hydrogen in the presence of a catalyst, such as palladium on carbon (Pd/C). The reaction involves the reductive amination of the aldehyde group, resulting in the formation of chloro 2 6 dimethylacetanilide.

Industrial Production

Chloro 2 6 dimethylacetanilide is produced industrially on a large scale using the Friedel-Crafts acylation method. The reaction is typically carried out in a batch reactor, with the reactants added in a controlled manner to maintain the desired reaction conditions.

The product is then isolated and purified through crystallization or distillation.

Applications and Uses

Chloro 2 6 dimethylacetanilide is a versatile compound with a wide range of applications in various industries.

One of its primary uses is as an intermediate in the production of other chemicals, such as dyes, pigments, and pharmaceuticals. In the pharmaceutical industry, it is used as a starting material for the synthesis of antipyretics, analgesics, and anti-inflammatory drugs.

Pharmaceutical Industry

• Synthesis of antipyretics (fever-reducing drugs), such as paracetamol (acetaminophen)
• Production of analgesics (pain relievers), such as phenacetin
• Manufacturing of anti-inflammatory drugs, such as ibuprofen

Agricultural Industry

In agriculture, chloro 2 6 dimethylacetanilide is used as a herbicide to control weeds in crops such as rice, wheat, and corn.

Textile Industry

In the textile industry, it is employed as a dye intermediate for the production of various dyes used in the coloration of fabrics.

Safety and Toxicity: A Chloro 2 6 Dimethylacetanilide

Chloro 2 6 dimethylacetanilide poses several potential hazards that necessitate careful handling and safety precautions.

This chemical is toxic upon ingestion, inhalation, or skin contact. It can cause irritation to the eyes, skin, and respiratory tract. Prolonged exposure may lead to more severe health effects, including damage to the liver, kidneys, and central nervous system.

Flammability

Chloro 2 6 dimethylacetanilide is a combustible material that can ignite under certain conditions. It has a flash point of 150°C (302°F) and an auto-ignition temperature of 400°C (752°F).

Environmental Impact

Chloro 2 6 dimethylacetanilide is harmful to aquatic organisms. It can accumulate in the environment and persist for long periods, posing a potential risk to ecosystems.

Safety Precautions

To ensure safe handling of chloro 2 6 dimethylacetanilide, it is crucial to follow these precautions:

• Wear appropriate personal protective equipment, including gloves, eye protection, and a respirator.
• Handle in a well-ventilated area.
• Avoid contact with skin, eyes, and clothing.
• Store in a cool, dry place away from incompatible materials.
• Dispose of waste according to local regulations.

Environmental Fate and Degradation

Chloro 2 6 dimethylacetanilide’s environmental fate and degradation play a crucial role in understanding its potential impact on ecosystems. This section explores its persistence, biodegradability, bioaccumulation potential, and methods for its degradation and removal from the environment.

Chloro 2 6 dimethylacetanilide exhibits moderate persistence in the environment, with a half-life of several months to years. Its biodegradability is limited, as it is resistant to microbial degradation. This persistence and limited biodegradability contribute to its potential for accumulation in the environment.

Bioaccumulation Potential

Chloro 2 6 dimethylacetanilide has a moderate potential for bioaccumulation in aquatic organisms. It can accumulate in fish and other aquatic species through the food chain, reaching concentrations that may pose risks to their health and survival.

Degradation and Removal Methods

Several methods are employed to degrade and remove chloro 2 6 dimethylacetanilide from the environment:

• Photolysis:Sunlight can break down chloro 2 6 dimethylacetanilide into smaller, less harmful compounds.
• Biodegradation:Certain microorganisms can slowly break down chloro 2 6 dimethylacetanilide over time.
• Adsorption:Chloro 2 6 dimethylacetanilide can bind to soil particles and organic matter, reducing its mobility and availability to organisms.
• Chemical oxidation:Advanced oxidation processes, such as ozonation, can rapidly degrade chloro 2 6 dimethylacetanilide into harmless substances.

These methods contribute to the gradual breakdown and removal of chloro 2 6 dimethylacetanilide from the environment, mitigating its potential risks to ecosystems.

Regulatory Status and Compliance

Chloro 2 6 dimethylacetanilide is subject to various regulations governing its production, use, and disposal. These regulations aim to protect human health and the environment from potential risks associated with the chemical.

In the United States, the Environmental Protection Agency (EPA) regulates chloro 2 6 dimethylacetanilide under the Toxic Substances Control Act (TSCA). TSCA requires manufacturers and importers to report production and use information for certain chemicals, including chloro 2 6 dimethylacetanilide.

Production and Use

• Manufacturers must notify the EPA 90 days before commencing production or import of chloro 2 6 dimethylacetanilide.
• Producers and importers must maintain records of production, use, and disposal of the chemical.
• The EPA may impose restrictions on the production, use, or disposal of chloro 2 6 dimethylacetanilide if it determines that the chemical poses an unreasonable risk to human health or the environment.

Disposal, A chloro 2 6 dimethylacetanilide

• Chloro 2 6 dimethylacetanilide must be disposed of in accordance with federal, state, and local regulations.
• Incineration is the preferred method of disposal for chloro 2 6 dimethylacetanilide.
• Landfills and wastewater treatment plants are not suitable for disposal of chloro 2 6 dimethylacetanilide.

Related Compounds and Analogues

Chloro 2,6-dimethylacetanilide is a member of a group of compounds known as acetanilides. These compounds share a common structural feature of an acetanilide group, which consists of an acetyl group (-COCH3) attached to an aniline ring (-NHC6H5).Acetanilides exhibit a range of biological activities, including analgesic, antipyretic, and anti-inflammatory properties.

Some of the most well-known acetanilides include paracetamol (acetaminophen), phenacetin, and aspirin.

Structural Similarities and Differences

Chloro 2,6-dimethylacetanilide differs from other acetanilides in the presence of two methyl groups (-CH3) attached to the aniline ring at positions 2 and 6. These methyl groups confer unique chemical and physical properties to the compound.

Potential Applications

Related acetanilides have found widespread use in various applications, including:

• -*Pharmaceuticals

  Paracetamol is a commonly used over-the-counter pain reliever and fever reducer. Phenacetin was once a popular analgesic but is now rarely used due to its potential toxicity.

-*Dyes

Acetanilides are used as intermediates in the production of azo dyes, which are widely employed in the textile industry.

-*Rubber industry

Acetanilides are used as antioxidants and vulcanization accelerators in the rubber industry.

-*Photography

Acetanilides are used as developing agents in photography.

The specific applications of chloro 2,6-dimethylacetanilide are still being explored, but its unique structural features may make it suitable for specialized applications in the pharmaceutical, chemical, or agricultural industries.

Research and Development

Research and development efforts related to 4-chloro-2,6-dimethylacetanilide are ongoing, driven by the potential for new applications and advancements in its synthesis and production. Scientists are exploring novel applications in various fields, including agriculture, pharmaceuticals, and materials science.

Synthesis and Production

Research is focused on developing more efficient and environmentally friendly methods for synthesizing 4-chloro-2,6-dimethylacetanilide. Alternative routes and catalysts are being investigated to reduce waste and improve yield. Additionally, researchers are exploring the use of renewable feedstocks to make the production process more sustainable.

New Applications

Emerging research explores the use of 4-chloro-2,6-dimethylacetanilide in novel applications, such as:

• As an active ingredient in herbicides and pesticides, due to its herbicidal and antifungal properties.
• In the development of new pharmaceuticals, owing to its potential biological activity.
• As a precursor in the synthesis of advanced materials, such as polymers and composites.

Challenges and Opportunities

Research in this field faces challenges, including the need for improved selectivity and efficiency in synthesis, as well as a thorough understanding of the environmental impact of 4-chloro-2,6-dimethylacetanilide. However, these challenges also present opportunities for innovation and the development of new technologies.

FAQ Explained

What is the IUPAC name of a chloro 2 6 dimethylacetanilide?

2-Chloro-N,N-dimethylacetanilide

What is the molecular formula of a chloro 2 6 dimethylacetanilide?

C8H10ClNO

What is the molar mass of a chloro 2 6 dimethylacetanilide?

169.62 g/mol

What is the physical state of a chloro 2 6 dimethylacetanilide at room temperature?

Solid

What color is a chloro 2 6 dimethylacetanilide?

White to off-white

What is the melting point of a chloro 2 6 dimethylacetanilide?

118-120 °C

What is the boiling point of a chloro 2 6 dimethylacetanilide?

295-297 °C

Is a chloro 2 6 dimethylacetanilide soluble in water?

Slightly soluble

Is a chloro 2 6 dimethylacetanilide flammable?

Yes

What are the potential hazards associated with a chloro 2 6 dimethylacetanilide?

Irritating to the skin, eyes, and respiratory tract. May cause allergic reactions.

What are the safety precautions for handling a chloro 2 6 dimethylacetanilide?

Wear appropriate protective clothing, gloves, and eye protection. Avoid contact with skin, eyes, and clothing. Use in a well-ventilated area.