2-bromo-4-methylpropiophenone is an organic compound with a phenyl ring attached to a propiophenone group, substituted by a bromine atom at the 2-position and a methyl group at the 4-position. It is a versatile and reactive compound used as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. This compound possesses potential biological activities such as antimicrobial, antifungal, and anti-inflammatory effects. However, it requires proper handling and safety precautions due to its potential hazards to health and safety. In pharmaceutical synthesis, it is utilized as a precursor in the production of analgesics, sedatives, and anticonvulsant drugs. Overall, 2-bromo-4-methylpropiophenone is a valuable compound with various applications in the pharmaceutical and chemical industries.
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Figure 1. 2-bromo-4-methylpropiophenone
2-bromo-4-methylpropiophenone is a chemical compound with several distinct properties. Firstly, it is an organic compound that falls under the category of aromatic ketones. It consists of a phenyl ring attached to a propiophenone group, where a bromine atom is substituted at the 2-position and a methyl group is substituted at the 4-position. Physically, 2-bromo-4-methylpropiophenone appears as a white or off-white crystalline powder. It has a characteristic odor and a molecular weight of approximately 227.10 g/mol. It is sparingly soluble in water but exhibits good solubility in various organic solvents such as ethanol, acetone, and chloroform. Chemically, this compound is known for its reactivity and versatility. It acts as an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and fine chemicals. It serves as a key building block in the production of different compounds through functional group transformations and further derivatization reactions. Moreover, 2-bromo-4-methylpropiophenone possesses certain pharmacological properties. It exhibits potential biological activities, including antimicrobial, antifungal, and anti-inflammatory effects. These properties make it a valuable compound in pharmaceutical research and drug discovery. Overall, 2-bromo-4-methylpropiophenone is a chemically active compound with various applications in the pharmaceutical and chemical industries. Its distinct properties make it an essential component in the synthesis of diverse compounds for numerous purposes. 1
2-bromo-4-methylpropiophenone, also known as bromo-methylpropiophenone, is a chemical compound widely used in pharmaceutical synthesis. This compound plays a crucial role in the synthesis of various pharmaceuticals due to its versatile reactivity. One of its major applications is as a precursor in the preparation of analgesics and sedatives. For example, it can be utilized as an intermediate in the synthesis of benzodiazepines, a class of drugs commonly used for their anxiolytic, hypnotic, and muscle relaxant properties. Furthermore, 2-bromo-4-methylpropiophenone is employed in the production of anticonvulsant drugs, which are used to treat conditions such as epilepsy. It serves as a key building block in the synthesis of these medications, allowing for the introduction of necessary functional groups and ensuring the desired pharmacological activity. In summary, 2-bromo-4-methylpropiophenone is a valuable compound in pharmaceutical synthesis. Its inclusion in the production of analgesics, sedatives, and anticonvulsant drugs showcases its significance in the development of medications that alleviate pain, promote relaxation, and combat seizure disorders. 2
2-bromo-4-methylpropiophenone is a chemical compound that requires proper handling and safety precautions due to its potential hazards. It is important to wear personal protective equipment, including face protection, when handling this compound. Adequate ventilation should also be ensured to prevent inhalation of the substance. To avoid skin irritation and injury, it is important not to get 2-bromo-4-methylpropiophenone in eyes, on skin, or on clothing. If contact does occur, affected areas should be flushed with water for at least 15 minutes and medical attention sought if necessary. Ingestion and inhalation of this substance should be avoided, as they can result in serious health effects such as respiratory irritation, pulmonary edema, and even death in extreme cases. Dust formation should also be avoided as it can lead to inhalation of the substance and subsequent health risks. In conclusion, it is crucial to follow appropriate safety measures when handling 2-bromo-4-methylpropiophenone to avoid potential hazards to health and safety. Proper personal protective equipment, adequate ventilation, and avoiding skin and eye contact, ingestion, inhalation, and dust formation are all essential steps in ensuring safe handling of this chemical compound. 3
1. PubChem. COMPOUND SUMMARY: 2-Bromo-4'-methylpropiophenone. National Library of Medicine 2005, CID: 2734063
2. Morgan Phil etc. Development and validation of a presumptive color spot test method for the detection of piperazine analogues in seized illicit materials, Anal Methods, 2013, 5: 5402-5410
3. SAFETY DATA SHEET: 2-Bromo-4'-methylpropiophenone. Fishersci, 2020, Cat No.: H64881.
2-bromo-4-methylpropiophenone employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field. Specifically, this chemical can act as the intermediate in the synthesis of 4-methyl methcathinone HCl (mephedrone HCl or 4-MMC HCl), which is used as the sample for development and validation of a presumptive color spot test method for the detection of piperazine analogues in seized illicit materials [1]. 4-MMC HCl is an illegal drug, which takes a lot of side effects, such as dilated pupils, poor concentration, short-term memory loss, illusion, delusions and erratic behavior, so it is necessary to develop the related reagents and ketone products to detect its abuse [2].
Scheme 1 The preparation of 4-MMC HCl from 2-bromo-4-methylpropiophenone
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4-MMC HCl was synthesized in two stages (Scheme 1). The first α-bromination step involved reacting 4-methylpropiophenone with excess bromine (to form 2-bromo-4-methylpropiophenone) in the presence of glacial acetic acid at 25 °C for 1 hour. The reaction solution was poured into ice-cold water and the 2-bromo-4-methylpropiophenone was extracted with dichloromethane and concentrated under vacuum to form yellow, fluffy crystals. The final methamination step involved combining equal molar NaOH and methylamine hydrochloride solutions. This solution was then added dropwise over 1 hour to a stirred solution of 2-bromo-4-methylpropiophenone in toluene, and the mixture was allowed to stir for 32 hours at 25 °C and poured into ice-cold water. The toluene layer was separated and acidified with dilute HCl solution, then the acidic extracts were washed with toluene before evaporating the aqueous layer to dryness to afford the crude 4-MMC HCl product as mottled light brown/brown colored, flaky crystals. Finally, the fine, white powder was collected following recrystallisation from isopropanol [3]. The final product 4-MMC HCl was analyzed by using various chromatographic, spectroscopic, mass spectrometry platforms and X-ray crystal structure analysis. These analyses are helpful to set up rapid qualitative analysis of 4-MMC HCl.
Since 2-bromo-4-methylpropiophenone is the intermediate for the drug, it was controlled by relevant departments.
[1] https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7946938.htm
[2] Shisheng Lin etc., CN106749622A, 4-methyl methcathinone antigen as well as preparation method and application thereof in detection of colloidal gold, 2016
[3] Morgan Phil etc., Development and validation of a presumptive color spot test method for the detection of piperazine analogues in seized illicit materials, Anal. Methods, 2013, 5, 5402-5410
2-bromo-4-methylpropiophenone employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field. Specifically, this chemical can act as the intermediate in the synthesis of 4-methyl methcathinone HCl (mephedrone HCl or 4-MMC HCl), which is used as the sample for development and validation of a presumptive color spot test method for the detection of piperazine analogues in seizing illicit materials [1]. 4-MMC HCl is an illegal drug, which takes a lot of side effects, such as dilated pupils, poor concentration, short-term memory loss, illusion, delusions and erratic behavior, so it is necessary to develop the related reagents and ketone products to detect its abuse [2].
Scheme 1 The preparation of 4-MMC HCl from 2-bromo-4-methylpropiophenone
4-MMC HCl was synthesized in two stages (Scheme 1). The first α-bromination step involved reacting 4-methylpropiophenone with excess bromine (to form 2-bromo-4-methylpropiophenone) in the presence of glacial acetic acid at 25 °C for 1 hour. The reaction solution was poured into ice-cold water and the 2-bromo-4-methylpropiophenone was extracted with dichloromethane and concentrated under vacuum to form yellow, fluffy crystals. The final methamination step involved combining equal molar NaOH and methylamine hydrochloride solutions. This solution was then added dropwise over 1 hour to a stirred solution of 2-bromo-4-methylpropiophenone in toluene, and the mixture was allowed to stir for 32 hours at 25 °C and poured into ice-cold water.
The toluene layer was separated and acidified with dilute HCl solution, then the acidic extracts were washed with toluene before evaporating the aqueous layer to dryness to afford the crude 4-MMC HCl product as mottled light brown/brown colored, flaky crystals. Finally, the fine, white powder was collected following recrystallisation from isopropanol [3]. The final product 4-MMC HCl was analyzed by using various chromatographic, spectroscopic, mass spectrometry platforms and X-ray crystal structure analysis. These analyses are helpful to set up rapid qualitative analysis of 4-MMC HCl.
Since 2-bromo-4-methylpropiophenone is the intermediate for the drug, it was controlled by relevant departments.
[1] https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7946938.htm
[2] Shisheng Lin etc., CN106749622A, 4-methyl methcathinone antigen as well as preparation method and application thereof in detection of colloidal gold, 2016
[3] Morgan Phil etc., Development and validation of a presumptive color spot test method for the detection of piperazine analogues in seized illicit materials, Anal. Methods, 2013, 5, 5402-541
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