product_name |
2-Acetonaphthone |
CAS_number |
93-08-3 |
formula |
C12H10O |
molar_mass |
170.21 g/mol |
pub_chem_CID |
7048 |
drug_bank |
NA |
chem_spider |
6782 |
bioavailability |
NA |
protein_binding |
NA |
metabolism |
NA |
elimination_halflife |
NA |
FAQ
What is 2-Acetonaphthone, and where is it commonly used?
2-Acetonaphthone is an organic compound
with the chemical formula C12H10O. It is a naphthyl ketone, meaning it consists of a naphthalene ring
bound to a carbonyl group. This compound is commonly encountered as a pale yellow crystalline solid and
has a slightly sweet, pleasant odor. 2-Acetonaphthone possesses numerous applications across various
industries. Primarily, it is commonly used as an intermediate in the synthesis of various chemicals,
including pharmaceuticals and agrochemicals. 2-Acetonaphthone's unique structure makes it particularly
valuable for creating specific organic compounds. Additionally, the compound serves as a fragrance
ingredient in the cosmetic industry due to its pleasant scent. It can also be utilized in the synthesis
of dyes and other coloration agents in the textile industry. Another notable application is its role as
a photoinitiator in polymerization reactions, where it can assist in the production of high-quality
plastics and resins. This multifaceted functionality makes 2-Acetonaphthone a highly sought-after
compound in both industrial and commercial applications.
What are the safety precautions when
handling 2-Acetonaphthone?
Handling 2-Acetonaphthone requires adherence to stringent safety
protocols to ensure a safe working environment. First and foremost, one should always wear appropriate
personal protective equipment (PPE), which includes gloves, safety goggles, and lab coats or protective
clothing. This minimizes direct skin contact and prevents exposure to the eyes. Work in a
well-ventilated area or use appropriate engineering controls such as fume hoods to avoid inhalation of
any dust or vapors. In case of skin contact, wash the area thoroughly with soap and water. If the
substance comes into contact with the eyes, rinse immediately with plenty of water and seek medical
attention. It is also crucial to know the compound's Material Safety Data Sheet (MSDS) and keep it
readily accessible in case of emergencies. Ensure that 2-Acetonaphthone is stored in a cool, dry place
away from incompatible substances such as strong oxidizing agents. Proper labeling of storage containers
is vital to prevent accidental misuse. Waste disposal must comply with local, state, and federal
regulations so be sure to follow proper laboratory waste management protocols. Given these safety
measures, a thorough understanding of the compound's properties and potential risks can help mitigate
hazards while handling 2-Acetonaphthone.
How is 2-Acetonaphthone synthesized?
The synthesis
of 2-Acetonaphthone is typically achieved through Friedel-Crafts acylation, a common method in organic
chemistry for adding acyl groups to aromatic systems. In this process, naphthalene acts as the aromatic
substrate, while acetyl chloride or acetic anhydride serves as the acylating agent. An acid catalyst,
often aluminum chloride (AlCl3), is used to facilitate the reaction. The general procedure involves
dissolving naphthalene in a suitable solvent such as dichloromethane, then gradually adding the
acetylating agent and the aluminum chloride catalyst. The mixture is stirred under controlled
temperature conditions to ensure the formation of 2-Acetonaphthone. Once the reaction is complete, the
mixture is quenched with water or another aqueous solution to neutralize the catalyst and then extracted
with an organic solvent to isolate the product. The crude product often requires purification, which can
be achieved through recrystallization or column chromatography, yielding high-purity 2-Acetonaphthone.
This methodology is widely favored because it offers a relatively simple and efficient way to synthesize
2-Acetonaphthone, making it accessible for both research and industrial applications. Advanced
techniques and alternative methods also exist, but the Friedel-Crafts acylation remains the cornerstone
for producing this versatile compound.
What are the physical and chemical properties of
2-Acetonaphthone?
2-Acetonaphthone possesses distinct physical and chemical properties that make it
particularly useful in both industrial and research settings. Physically, it appears as a pale yellow
crystalline solid, which is relatively stable under standard conditions. The compound has a melting
point typically ranging between 75°C to 77°C, and a boiling point around 295°C. It is moderately soluble
in organic solvents like ethanol, methanol, and dichloromethane, but only sparingly soluble in water.
Chemically, 2-Acetonaphthone exhibits the characteristics typical of naphthyl ketones. The presence of
the carbonyl group (C=O) attached to the naphthalene ring introduces a degree of reactivity that can be
exploited in various chemical reactions. It can participate in nucleophilic addition reactions, forming
secondary alcohols when reduced. Due to the aromatic ring, 2-Acetonaphthone can also undergo
electrophilic aromatic substitution, allowing further functionalization of the compound. The compound’s
mild aromatic nature contributes to its stability, making it less reactive compared to aliphatic
ketones, yet sufficiently reactive to serve as an intermediate in organic synthesis. The combination of
these properties makes 2-Acetonaphthone a versatile and valuable compound in numerous applications,
including pharmaceuticals, cosmetics, and materials science.
Are there any specific
environmental concerns associated with 2-Acetonaphthone?
While 2-Acetonaphthone is valuable in
various applications, it is essential to consider its potential environmental impact. As with many
organic compounds, improper handling and disposal can pose environmental risks. In aquatic environments,
for example, 2-Acetonaphthone may exhibit moderate toxicity to aquatic organisms; therefore, preventing
contamination of water bodies is crucial. Effluents containing this compound should undergo proper
treatment before discharge to mitigate any harmful impacts on aquatic systems. Additionally, the
compound's persistence in soil and water is a subject of environmental concern, as it can lead to
bioaccumulation in living organisms. To address these concerns, it’s vital to implement stringent waste
management practices when using 2-Acetonaphthone. This includes following guidelines for safe disposal,
utilizing designated chemical waste containers, and ensuring that contaminated materials are treated
appropriately before disposal. The compound should never be poured down the drain or disposed of in
regular trash to avoid unnecessary environmental exposure. Regulatory guidelines from agencies such as
the Environmental Protection Agency (EPA) provide frameworks for the responsible use and disposal of
chemical substances like 2-Acetonaphthone. Adhering to these guidelines can help mitigate the
environmental footprint, ensuring that the compound’s benefits are harnessed without compromising
ecological integrity.