As a chemical raw material, 4′-Methylpropiophenone is a chemical reagent for electrocarboxylation reaction. It is a pharmaceutical intermediate of Naomaining, which can be used as organic synthetic intermediates and pharmaceutical intermediates, mainly used in laboratory research and development process and chemical production process. It is an organic compound with the chemical formula C10H12O. It is a colorless liquid, usually with aromaticity smell. Its state of matter is liquid at room temperature. Easily soluble in organic solvents such as ethanol, ether, acetone, and benzene. Its solubility in water is relatively low. The melting point and boiling point of are -20 ℃ and 238 ℃, respectively. This indicates that it is a compound with a high boiling point. Under normal conditions, it is a relatively stable compound, but it is flammable and should avoid contact with open flames or heat sources.
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Chemical Formula |
C10H12O |
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Exact Mass |
148.09 |
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Molecular Weight |
148.21 |
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m/z |
148.09 (100.0%), 149.09 (10.8%) |
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Elemental Analysis |
C, 81.04; H, 8.16; O, 10.80 |
Preparation Methods
Clemmensen reduction method
- Acetophenone undergoes a sulfate reduction reaction under the Zn-Hg/HCl system to generate a methylcarbene intermediate of 4'-Methylpropiophenone.
- React the methylcarbene intermediate with Hg in the Hg/HCl system, and reduce it again to generate 4'-Methylpropiophenone.
This method is easy to operate, but it also has great harm to the environment and human health.
Molecular sieve catalytic method
- Reacting acetophenone and isopropanol under the catalysis of a molecular sieve catalyst to obtain 2-Methyl-5-isopropylcyclohexanone.
- Oxidize 2-Methyl-5-isopropylcyclohexanone and CrO3 in the presence of K2CO3 to obtain 4'-Methylpropiophenone.
The method has mild reaction conditions, and the molecular sieve catalyst is easy to recover.
Wadsworth-Emmons synthesis method
- Reacting alkyl phosphonate and acetophenone under alkaline conditions to generate acetophenone alkyl phosphonate.
- React alkyl phosphonic acid acetophenone ester with ethyl acetate under alkaline conditions to generate 4'-Methylpropiophenone.
This method is simple to operate, but requires more reagents and longer reaction time.
The synthesis method of 4′-Methylpropiophenone was that α-7, α-hydroxy-4-methyl-phenylacetic acid was synthesized by electrosynthesis of α-7, α-hydroxy-4-methyl-phenylacetic acid with carbon dioxide fixed by p-methyl phenylpropanone induced by chiral adsorption inducer alkaloid. The high yield and a certain ee value were obtained by constant current electrolysis and high performance liquid phase gun measurement. Through the preliminary chemicalbook investigation of the electrode material, current density, inducer and other factors of the reaction, it was found that the yield of 37.39 % and the ee value of S-32.78 % were obtained by constant current electrolysis at the current density of 1 mA·Cm−2 with annular stainless steel as the cathode, magnesium rod as the sacrificial anode, tetrabutyl ammonium iodide as the electrolytic supporting salt, 0.016 g cinchonine as the inducer and 0 °C.
Synthetic drugs
For example, it is one of the important raw materials for the synthesis of drugs such as ephedrine and pseudoephedrine. In addition, 4'-Methylpropiophenone can also be used to prepare psychotropic drugs such as MDMA. These drugs have different effects, such as refreshing, stimulating, antidepressant, etc., so they have a wide range of applications in medical and scientific research.
Industrial field
It can be used as a solvent and intermediate, and is widely used in chemical and industrial fields. For example, it can be used in synthetic resins, dyes, paints, plastics, etc. In addition, it can also be used to prepare rubber processing aids, surfactants, spices and other products.
Scientific research
For example, in the field of astrochemistry, it can be used to analyze organic molecules in solar system planets and meteorites. In addition, 4'-Methylpropiophenone can also be used to study chemical reactions, catalysts and other fields.
Agricultural field
It can be used as a raw material for insecticides and mosquito repellants, and is widely used in agricultural fields. For example, it can be used to prepare insecticides such as acetyl chloride and bitter ketone. These insecticides and mosquito repellents can effectively control pests and mosquitoes, improve crop yields and human health.
Cosmetics and spices
It can also be used in cosmetics and fragrances. It can be used to prepare aromatic compounds and is widely used in perfumes, cosmetics, soaps, shampoos and other products. These compounds have different fragrances and effects, and can meet different needs by deploying different spices.
Discovery & Devolopment History
The discovery history of p-Methylacetophenone, also known as 4′-Methylpropiophenone, is a fascinating journey spanning centuries of chemical exploration and scientific development. While the exact date of its first synthesis is not precisely known, its history can be traced back to the earliest days of organic chemistry.
Early organic chemists were fascinated by the potential of compounds containing both aromatic rings and carbonyl groups, as they offered unique chemical reactivity and potential for synthesis. As the field of organic synthesis matured, chemists began to experiment with different combinations of substituents on aromatic rings, seeking to understand their effect on the reactivity and properties of the resulting compounds.
4′-Methylpropiophenone emerged as a compound of particular interest due to its potential applications in both industrial and pharmaceutical settings. Its discovery was likely the result of extensive experimentation and synthesis efforts by organic chemists seeking to prepare new compounds with desired properties.
Over time, as scientific methods and techniques improved, chemists were able to synthesize p-Methylacetophenone in larger quantities and with higher purity. This allowed for more detailed studies of its chemical properties and reactivity, leading to the discovery of its many potential applications.
It is an important intermediate in organic synthesis, which has experienced a century of development. As early as the end of the 19th century and the beginning of the 20th century, German chemists Friedel and Crafts proposed a method for synthesizing 4'-Methylpropiophenone through the Friedel-Crafts reaction catalyzed by acetophenone and aluminum trichloride. After that, many scholars improved and optimized this method, such as the Clemmensen reduction method using zinc as the reducing agent, and the molecular sieve catalytic method using molecular sieve catalysts.
In recent years, with the continuous development of organic synthesis technology, various new synthetic methods have been proposed, among which the method of catalyst optimization as the main method has gradually become a research hotspot. Routine methods such as the use of Wadsworth-Emmons reagent, Pd/Ni bimetallic palladium catalysis, and CrO3 oxidation have been greatly optimized. For example, Solvent-free synthesis and 1-(4-methylphenyl)ethanone via Aza-Michael addition in 2013 and Accelerating the synthesis by encapsulating it with beta-cyclodextrin, P. quinquecorneus in 2019 The 3,4-methylcyclohexanone and other methods catalyzed by the SBB-PQ catalyst not only have a fast reaction rate and mild reaction conditions, but also have high product purity, less waste, and are more friendly to the environment and human health.
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