4-Methylpropiophenone CAS 5337-93-9 (also commonly referred to as para-methylpropiophenone or 4'-methylpropiophenone) is a simple aromatic ketone that serves as an important chemical intermediate in organic synthesis. Its structure features an electron-donating methyl group on the aromatic ring, which modifies its reactivity compared to unsubstituted propiophenone. It is a known precursor in both legitimate pharmaceutical synthesis and illicit drug manufacturing, making it a controlled substance in many jurisdictions.
Nombre :
4-MethylpropiophenoneN.º CAS :
5337-93-9MF :
C₁₀H₁₂OMW :
148.20Pureza :
≥99%Apariencia :
Typically a colorless to pale yellow liquid.Condición de almacenamiento :
Store in a cool, well-ventilated area away from ignition sources.Chemical Properties
Chemical Name: 1-(4-Methylphenyl)propan-1-one
IUPAC Name: 1-(4-Methylphenyl)propan-1-one
Synonyms: p-Methylpropiophenone; 4'-Methylpropiophenone; 4-Methylpropiophenone; 1-Propanone, 1-(4-methylphenyl)-
CAS Registry Number: 5337-93-9
Molecular Formula: C₁₀H₁₂O
Molecular Weight: 148.20 g/mol
Chemical Structure: Consists of a benzene ring (phenyl group) with a methyl substituent at the 4- (or para-) position and a propanoyl group (CH₃CH₂C=O) attached at the 1-position. This α-alkylated acetophenone structure is key to its reactivity.
Appearance: Typically a colorless to pale yellow liquid. May appear as a low-melting solid at cooler temperatures.
Odor: Characteristic sweet, floral, or acetone-like odor.
Boiling Point: ~239-241 °C (at atmospheric pressure)
Melting Point: ~10-12 °C
Density: ~1.00 - 1.01 g/cm³ at 20 °C
Solubility: Soluble in most organic solvents (ethanol, ether, acetone, chloroform). Practically insoluble in water.
Refractive Index: n²⁰/D ~1.525 - 1.527
Stability: Stable under normal conditions but may darken over time due to oxidation. Incompatible with strong oxidizing agents and strong bases. Sensitive to light.
Biological Activities
4-Methylpropiophenone itself is not considered an active pharmaceutical ingredient (API) and has no established therapeutic use.
Intermediate Role: Its primary biological relevance is solely as a chemical precursor. Its structure is incorporated into more complex molecules during synthesis.
Toxicity Profile: Data is limited. It is expected to have moderate toxicity based on its structural class. May cause skin, eye, and respiratory tract irritation. Harmful if swallowed or inhaled. It is an organic ketone and should be treated as a potential irritant and central nervous system depressant at high concentrations.
Metabolism: Like similar ketones, it would likely undergo reduction and conjugation in biological systems, but specific metabolic pathways are not well-characterized for this compound.
Biosynthesis
4-Methylpropiophenone is not a natural product and is not produced via biological pathways. It is synthesized industrially and in laboratories through chemical synthesis.
Primary Synthetic Route: Friedel-Crafts Acylation. This is the most common and efficient method.
1.Substrates: p-Xylene (1,4-dimethylbenzene) or toluene can be used as the aromatic component.
2.Acylating Agent: Propionyl chloride or propionic anhydride.
3.Catalyst: A Lewis acid catalyst, typically aluminum chloride (AlCl₃) or ferric chloride (FeCl₃).
4.Reaction: The catalyst activates the acylating agent, which electrophilically attacks the aromatic ring of p-xylene or toluene, followed by deprotonation to yield the ketone. When starting from p-xylene, selective mono-acylation under controlled conditions is required.
Alternative Route: Oxidation of the corresponding secondary alcohol (1-(4-methylphenyl)propan-1-ol).
Applications
FAQs
Q1: What is the main legitimate industrial use of 4-methylpropiophenone?
A1: Its primary legitimate use is as a versatile chemical intermediate in fine organic synthesis, particularly in research and development settings for creating more complex compounds in pharmaceuticals and fragrances. However, its use is heavily overshadowed and regulated due to its role as a drug precursor.
Q2: Is CAS 5337-93-9 a controlled substance?
A2: Yes, it is highly regulated globally. It is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances (1988). Most countries, including the USA (DEA List I Chemical), Canada, EU member states, Australia, and China, have enacted laws strictly controlling its trade. Legitimate transactions require licenses, reporting, and are subject to law enforcement monitoring.
Q3: Can a legitimate company purchase this chemical?
A3: Yes, but under extremely strict conditions. Only verified companies (e.g., licensed pharmaceutical manufacturers, accredited analytical laboratories, forensic institutions) with a demonstrable, lawful end-use can apply for the necessary permits. The process involves rigorous customer identification, end-use verification, and detailed transaction reporting to national authorities.
Q4: How should it be stored safely?
A4: Store in a cool, well-ventilated area away from ignition sources. Keep container tightly closed in a dark, locked cabinet or safe appropriate for controlled substances. It should be stored separately from strong oxidizers and bases. Due to its precursor status, physical security and inventory control are as critical as chemical safety.
Q5: What analytical methods are used for its identification?
A5: Common methods include:
Gas Chromatography-Mass Spectrometry (GC-MS): For identification and purity analysis.
Fourier-Transform Infrared Spectroscopy (FT-IR): To identify functional groups (carbonyl, aromatic ring).
Nuclear Magnetic Resonance (NMR) Spectroscopy: (¹H and ¹³C) for definitive structural confirmation.
Refractive Index and Boiling Point: As supporting physical property data.
Q6: What safety precautions are required for handling?
A6:
Personal Protective Equipment (PPE): Use in a fume hood. Wear chemical-resistant gloves (nitrile), safety goggles, and a lab coat.
Hazards: Flammable liquid and vapor. Harmful if inhaled, swallowed, or absorbed through skin. Causes skin and eye irritation.
Spill: Absorb with inert material (sand, vermiculite), place in a sealed container, and dispose of as hazardous waste in accordance with local regulations.
Disclaimer: This information is for regulatory, forensic, and chemical safety reference only. 4-Methylpropiophenone (CAS 5337-93-9) is a controlled precursor chemical. Any activities involving this substance are subject to stringent national and international laws. This document does not constitute legal or safety advice. Compliance with all applicable regulations is the sole responsibility of the user. Unauthorized manufacture, distribution, or possession is illegal.
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