5586-88-9 Usage
Description
4-Chlorophenylacetone, a phenylacetone derivative, is a clear light yellow liquid with significant applications in the pharmaceutical industry. It is known for its role in the preparation of biologically active compounds, particularly anorectic agents, which are substances that suppress appetite.
Uses
Used in Pharmaceutical Industry:
4-Chlorophenylacetone is used as a key intermediate in the synthesis of anorectic agents for the treatment of obesity and related health conditions. Its chemical structure allows for the development of compounds that can effectively suppress appetite, aiding in weight management and overall health improvement.
Used in Chemical Research:
As a phenylacetone derivative, 4-Chlorophenylacetone is also utilized in various chemical research applications, where it serves as a starting material for the synthesis of other biologically active molecules. Its unique properties make it a valuable component in the development of new pharmaceuticals and chemical compounds with potential therapeutic applications.
Preparation
At present, there are three main synthetic routes for 4-chlorophenylacetone. The first is to synthesize 4-chlorophenylacetone with sodium p-chlorobenzenesulfonate and acetone as raw materials, with a yield of about 54%. The second synthesis route is to synthesize 4-chlorophenylacetone with p-chlorobenzenesulfonyl chloride and chloroacetone as raw materials. The third synthesis route is to synthesize 4-chlorophenylacetone from chloroacetone.
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 2590, 1983 DOI: 10.1021/jo00163a034
Health Hazard
When it contacts with skin and mucous membrane, 4-chlorophenylacetone will cause inflammation, so pay attention to safety when using 4-chlorophenylacetone. This chemical is harmful to environment. It should be prevented from contacting groundwater, waterways or sewage systems. Without government permission, 4-chlorophenylacetone should not be discharged into the surrounding environment.
Check Digit Verification of cas no
The CAS Registry Mumber 5586-88-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,8 and 6 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5586-88:
(6*5)+(5*5)+(4*8)+(3*6)+(2*8)+(1*8)=129
129 % 10 = 9
So 5586-88-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H9ClO/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5H,6H2,1H3
5586-88-9Relevant articles and documents
Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity
Chen, Ching-Nung,Cheng, Wei-Min,Wang, Jian-Kai,Chao, Tzu-Hsuan,Cheng, Mu-Jeng,Liu, Rai-Shung
supporting information, p. 4479 - 4484 (2021/01/21)
This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.
Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai
supporting information, p. 6961 - 6966 (2021/09/11)
An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
Direct Synthesis of Propen-2-yl Sulfones through Cascade Reactions Using Calcium Carbide as an Alkyne Source
Gao, Lei,Liu, Zhenrong,Ma, Xiaolong,Li, Zheng
supporting information, p. 5246 - 5250 (2020/07/04)
A simple method for the construction of propen-2-yl sulfones through cascade reactions of calcium carbide with arylsulfonylhydrazones using copper as a mediator is described. The salient features of this protocol are the use of readily available and easy-to-handle alkyne source, broad substrate scope, open-air condition, and simple operation procedure.