29363-97-1

Basic information

• Product Name: 5-Isoxazolecarboxylic acid, 3-(4-chlorophenyl)-, ethyl ester
• CAS NO: 29363-97-1
• Molecular Formula: C12H10ClNO3
• Molecular Weight: 251.669
• Mol File: 29363-97-1.mol

Chemical Properties

• CAS DataBase Reference: 5-Isoxazolecarboxylic acid, 3-(4-chlorophenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isoxazolecarboxylic acid, 3-(4-chlorophenyl)-, ethyl ester(29363-97-1)
• EPA Substance Registry System: 5-Isoxazolecarboxylic acid, 3-(4-chlorophenyl)-, ethyl ester(29363-97-1)

Safety Data

• Hazardous Substances Data: 29363-97-1(Hazardous Substances Data)

Upstream product

• 15500-74-0 4-chlorobenzonitrile N-oxide 
• 623-47-2 propynoic acid ethyl ester 
• 3848-36-0 4-chlorobenzaldoxime 
• 294624-23-0 (Z)-ethyl 4-(4-chlorophenyl)-2-hydroxy-4-oxo-2-butenoate 
• 99-91-2 para-chloroacetophenone 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 28123-63-9 4-chlorobenzohydroximoyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 3717-24-6 4-chlorobenzaldehyde oxime 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 140-88-5 ethyl acrylate 

Downstream Products

• 338982-11-9 3-(4-chlorophenyl)-5-isoxazolylcarboxylic acid 

Relevant articles and documents

Synthesis and mechanistic studies of diketo acids and their bioisosteres as potential antibacterial agents

A series of diketo esters and their pertinent bioisosteres were designed and synthesized as potent antibacterial agents by targeting methionine amino peptidases (MetAPs). In the biochemical assay against purified MetAPs from Streptococcus pneumoniae (SpMe

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles

Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.

A facile one-pot synthesis of 3,5-disubstituted isoxazole derivatives using hydroxy (tosyloxy) iodobenzene

Hydroxy (tosyloxy) iodobenzene (HTIB), a hypervalent iodine reagent, has been extensively used for oxidative transformations. We have developed a one-pot synthesis wherein aldoximes when reacted with alkynes in the presence of HTIB result in the direct formation of isoxazoles. This simple and straightforward reaction allows for ease of purification while leading to the formation of high purity 3,5-disubstituted isoxazoles in moderate yields.

Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes: Studying the reaction course

Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes to nitrile oxides were studied in details. In presence of external radical source, TEMPO, these reagents did not furnish nitrile oxides, instead favoured deoximation to aldehydes. A common trend of deoximation was established from electronically tuned aldoximes, which is: aliphatic>aromatic> aldoximes with strong electron-withdrawing group, though the extent of deoximation was less in case of CrO2. Above effects were not observed with chloramine-T and diacetoxyiodobenzene, reagents known to produce nitrile oxides via hydroximoyl halide or equivalent ionic intermediates. A putative reaction mechanism is proposed for MO2 (M=Cr, Mn) mediated oxidation of aldoximes through formation of a nitroso-oxime tautomeric pair. Formation of nitrile oxide is possibly occurred from the oxime tautomer via a σ-type iminoxy radical intermediate. The deoximation process, dominating in presence of external radical environment, is explained following decomposition of the nitroso tautomer.

Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve (CrO2)

Treatment of aldoximes 1 with Magtrieve (CrO2) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a-u and isoxazoles 6a-q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63-90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed through isolation of the dimerization product furoxane 2a in absence of any dipolarophile. The methodology has been extended to intramolecular nitrile oxide cycloaddition (INOC) reactions to access highly useful chromane derivatives 7-8 (75-80% isolated yields). Magtrieve, as a new reagent for 1,3-DC reactions, has offered excellent substrate generality and at the same time demonstrated tolerance toward sensitive protecting groups and electron-rich functional groups.

An efficient solid-phase synthesis of substituted isoxazole, triazole, and cycloalkadiene derivatives using supported selenium resin

We have developed efficient methods for the syntheses of 3,5-disubstituted isoxazoles and 1,2,3-triazoles, and 1,3- and 1,4-cycloalkadiene derivatives using polymer-supported selenium resin. The advantages of these methods include straightforward operation, lack of odor, good stability, and high purity of the products. Georg Thieme Verlag Stuttgart.

Synthesis of isoxazole-5-carboxylates by cyclization of oxime 1,4-dianions with diethyl oxalate

The cyclization of oxime dianions with diethyl oxalate afforded 4,5-dihydro-5-hydroxyisoxazole-5-carboxylates, which were transformed into isoxazole-5-carboxylates by acid-mediated dehydration. The reaction of the dilithiated oximes of cycloheptanone and