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Usage

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)-3-phenyl-2-oxazolidinone is used as a building block for the synthesis of pharmaceuticals due to its ability to contribute to the development of new cancer treatments. Its antitumor and cytotoxic activities make it a promising candidate for creating innovative medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(Chloromethyl)-3-phenyl-2-oxazolidinone is utilized as a key intermediate in the synthesis of various agrochemicals, leveraging its structural properties to enhance the effectiveness of these products.
Used in Fine Chemicals Synthesis:
5-(Chloromethyl)-3-phenyl-2-oxazolidinone is employed as an intermediate in the production of fine chemicals, where its unique reactivity allows for the creation of a broad spectrum of functionalized molecules with diverse applications.
Overall, 5-(chloromethyl)-3-phenyl-2-oxazolidinone is a valuable compound with a wide range of applications across different industries, particularly in the development of pharmaceuticals, agrochemicals, and other specialty chemical products. Its potential for further research and development underscores its importance in the field of organic synthesis.

Upstream product

• 2651-82-3 phenyl-carbamic acid-(β,β'-dichloro-isopropyl ester) 
• 103-72-0 phenyl isothiocyanate 
• 106-89-8 epichlorohydrin 
• 103-71-9 phenyl isocyanate 
• 132783-14-3 cis-2-(phenylimino)-4,5-dimethyl-1,3-dioxolane 
• 62-53-3 aniline 
• 1260086-07-4 methyl 3-chloro-2-hydroxypropyl(phenyl)carbamate 
• 169268-95-5 tert-butyl allyl(phenyl)carbamate 
• 124-38-9 carbon dioxide 
• 76226-32-9 N-(3-chloro-2-hydroxypropyl)aniline 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 1228268-43-6 C₁₆H₁₄N₄O₂ 
• 1071789-03-1 3-phenyl-5-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one 
• 367925-74-4 5-azidomethyl-3-phenyl-1,3-oxazolidin-2-one 
• 1228268-42-5 C₁₂H₁₂N₄O₂ 

Relevant academic research and scientific papers

Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones

An electrostatically enhanced phenol is utilized as a straightforward, sustainable, and potent one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20-60 min). A careful assessment of the efficacy of various positively charged phenols and anilines and the impact of several factors, such as catalyst loading, temperature, and the kind of nucleophile, on catalytic reactivity were examined. Under neat conditions, this one-component catalytic platform was exploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substituted epoxides and isocyanates within minutes, where up to 96% yield and high degree of selectivity were attained. DFT calculations to achieve reaction barriers for different catalytic routes were conducted to provide mechanistic understanding and corroborated the experimental findings in which concurrent epoxide ring-opening and isocyanate incorporation were proposed.

Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones

Among the wide variety of heterocycles, 2-oxazolidinones are recognized as some of the most important heterocyclic compounds in medicinal chemistry. Therefore, the development of a practical method for their synthesis would be an important development. He

Method for synthesizing N - aryl oxazolidine -2 - ketone compound by ionic liquid catalysis

The invention discloses a method for catalytic synthesis of a N-aryloxazolane-2-one compound or a chiral N-aryloxazolane-2-one compound from an ionic liquid. The process of the preparation method is as follows: a catalytic amount of ionic liquid is added

Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones

Asymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of β-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbony

Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

Direct synthesis of oxazolidin-2-ones from tert-butyl allylcarbamate via halo-induced cyclisation

A novel synthetic pathway towards the 2-oxazolidinone derivatives involving the halo-induced cyclisation of tert-butyl allyl(phenyl)carbamate was successfully developed. Various halogenating reagents were evaluated under different reaction conditions for the reaction optimisation. Interestingly, the synthetic route to 2-oxazolidinone derivatives containing one halogen atom in the aliphatic site or two halogen atoms including the extra halogen atom substituted in the aryl group at the para position, were thoroughly established for all chloro-, bromo- and iodo compounds. Either halo-unsubstituted-aryl oxazolidinone or p-halo-substituted-aryl oxazolidinone could be selectively produced by selecting the appropriate choices of halogenated reagents and reaction conditions e.g. reaction time and temperature. Toloxatone, a commercial antidepressant, was successfully synthesized by using this developed method.

Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex

Chromium(salphen) complex 10 is found to be a catalyst for the preparation of oxazolidinones from epoxides and isocyanates. Using the optimal reaction conditions (1.5 mol % of chromium(salphen) complex 10 at 80 °C in toluene for 4 hours), six epoxides wer

Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Br?nsted acid/halide ion bifunctional catalyst that can accelerate epoxide ring opening with high regioselectivity. Mechanistic studies disclosed that the ylide generated from TAPS, along with the formation of halohydrins, plays a crucial role in the reaction with isocyanates.

Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations

A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stere

Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes

The combination of an aluminium(heteroscorpionate) complex and tetrabutylammonium bromide acts as a highly efficient catalyst system for the synthesis of oxazolidinones from epoxides and isocyanates. Twenty two complexes were tested derived from a range o