3-Methoxyacetophenone CAS 586-37-8 is a simple aromatic ketone derivative primarily recognized as a crucial chemical intermediate in organic synthesis. It belongs to the class of alkyl aryl ketones and is valued for its methoxy-substituted aromatic ring, which makes it a versatile and reactive building block, particularly in the pharmaceutical and fragrance industries.
Name :
3-MethoxyacetophenoneCAS No. :
586-37-8MF :
C₉H₁₀O₂MW :
150.17Purity :
98%Appearance :
a clear, colorless to pale yellow liquidChemical Properties
Chemical Name: 3-Methoxyacetophenone
Synonyms: 3’-Methoxyacetophenone; 3-Acetylanisole; 1-(3-Methoxyphenyl)ethan-1-one; m-Methoxyacetophenone
CAS Registry Number: 586-37-8
Molecular Formula: C₉H₁₀O₂
Molecular Weight: 150.17 g/mol
Chemical Structure: It consists of a benzene (phenyl) ring substituted with a methoxy group (–OCH₃) at the meta-position (carbon 3) and an acetyl group (–COCH₃) at carbon 1. Its structure is the key to its chemical reactivity.
Appearance: Typically a clear, colorless to pale yellow liquid at room temperature.
Odor: Characteristic sweet, floral, or honey-like odor, making it useful in fragrance applications.
Solubility: Soluble in most organic solvents (e.g., ethanol, ether, acetone, chloroform). Insoluble in water.
Melting Point: ~8 °C
Boiling Point: ~240-242 °C
Density: ~1.08 g/cm³ at 20 °C
Stability: Stable under recommended storage conditions. Incompatible with strong oxidizing agents, strong bases, and strong reducing agents. The carbonyl group is the primary reactive site.
Biological Activities
3-Methoxyacetophenone itself is not typically described as a final active pharmaceutical ingredient. Its primary biological significance lies in its role as a precursor. It serves as a key synthon for synthesizing more complex molecules that possess biological activity. Its derivatives are found in compounds with reported activities such as:
Pharmaceutical Intermediates: Used in the synthesis of therapeutic agents, including some with analgesic, anti-inflammatory, or central nervous system activity.
Antimicrobial Agents: Some derivatives synthesized from it have been explored for antimicrobial properties.
It is generally considered to have low to moderate acute toxicity. Always refer to the Safety Data Sheet (SDS) for detailed hazard information.
Biosynthesis
3-Methoxyacetophenone is not a common natural product and is not typically produced via biological pathways on an industrial scale. It is synthesized through chemical synthesis. Two common synthetic routes are:
1.Friedel-Crafts Acylation: The most common industrial method, involving the acylation of anisole (methoxybenzene) with acetic anhydride or acetyl chloride in the presence of a Lewis acid catalyst (e.g., aluminum chloride, AlCl₃). The reaction requires careful control to direct acylation to the meta-position.
2.Methylation: Methylation of 3-Hydroxyacetophenone using methylating agents like dimethyl sulfate or methyl iodide in the presence of a base.
Applications
FAQs
Q1: What is the main use of 3-Methoxyacetophenone?
A1: Its primary and most significant use is as a key chemical intermediate in the synthesis of more complex organic molecules, especially in the pharmaceutical sector for manufacturing active drug substances.
Q2: Is 3-Methoxyacetophenone a controlled substance or a precursor to illegal drugs?
AERN: 3-Methoxyacetophenone is a legitimate industrial chemical. However, as with many organic intermediates, it is important to note that it can be used in the synthesis of various compounds. It is the responsibility of the supplier and buyer to comply with all national and international laws, including those related to the monitoring of precursor chemicals that could be diverted for the illicit manufacture of controlled substances. Sales are subject to strict compliance checks.
Q3: How should it be stored and handled?
A3: Store in a cool, well-ventilated place away from heat, sparks, and open flames. Keep the container tightly closed. It should be stored separate from strong oxidizers, strong bases, and strong reducing agents. Handle with appropriate personal protective equipment (PPE) such as gloves and safety goggles in a fume hood to avoid inhalation and contact.
Q4: Where can I buy 3-Methoxyacetophenone?
A4: It is available from reputable chemical suppliers, fine chemical manufacturers, and B2B platforms like LookChem, Made-in-China, and Alibaba. Buyers are screened, and sales are for legitimate business, research, and development purposes only.
Q5: Can you provide customization like specific purity or packaging?
A5: Yes, most professional suppliers offer various purity grades (e.g., 98%, 99%, HPLC grade) and packaging options (from 1kg bottles to 200kg drums) according to client specifications for industrial-scale use.
Q6: What is the difference between 2-, 3-, and 4-Methoxyacetophenone?
A6: They are structural isomers. The number indicates the position of the methoxy group on the benzene ring relative to the acetyl group. This positional difference significantly alters their physical properties (like melting point) and chemical reactivity, making them suitable for different synthetic pathways and end products.
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