22667-21-6

Basic information

• Product Name: Methyl 5-formylisoxazole-3-carboxylate
• Synonyms: 3-Isoxazolecarboxylicacid,5-formyl-,methylester(8CI,9CI);3-Isoxazolecarboxylic acid, 5-formyl-, methyl ester;Methyl 5-formyl-1,2-oxazole-3-carboxylate;Methyl 5-formylisoxazole-3-carboxylate
• CAS NO: 22667-21-6
• Molecular Formula: C6H5NO4
• Molecular Weight: 155.11
• Product Categories: OXAZOLE
• Mol File: 22667-21-6.mol

Chemical Properties

• Melting Point: 72-73 ºC
• Boiling Point: 306 ºC
• Flash Point: 139 ºC
• Appearance: /
• Density: 1.348
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.524
• PKA: -7.18±0.50(Predicted)
• CAS DataBase Reference: Methyl 5-formylisoxazole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-formylisoxazole-3-carboxylate(22667-21-6)
• EPA Substance Registry System: Methyl 5-formylisoxazole-3-carboxylate(22667-21-6)

Safety Data

• Hazardous Substances Data: 22667-21-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-formylisoxazole-3-carboxylate is used as a building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity enable the development of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, Methyl 5-formylisoxazole-3-carboxylate is utilized as a building block for the synthesis of agrochemicals. Its incorporation into these compounds can lead to the development of new pesticides or herbicides with improved efficacy and selectivity.
Used as a Reagent in Organic Chemistry:
Methyl 5-formylisoxazole-3-carboxylate is employed as a reagent for various organic transformations. Its reactivity allows for the synthesis of a wide range of nitrogen-containing compounds, expanding the scope of organic synthesis.
Used as a Precursor in the Production of Other Nitrogen-Containing Compounds:
Due to its versatile nature, Methyl 5-formylisoxazole-3-carboxylate serves as a precursor in the production of other nitrogen-containing compounds. Its use in this capacity contributes to the synthesis of a diverse array of chemical entities with potential applications in various industries.

InChI:InChI=1/C6H5NO4/c1-10-6(9)5-2-4(3-8)11-7-5/h2-3H,1H3

Upstream product

• 139297-55-5 methyl 5-(hydroxymethyl)isoxazole-3-carboxylate 
• 252769-66-7 methyl 5-(tetrahydro-2H-pyran-2-yloxymethyl)isoxazole-3-carboxylate 

Relevant articles and documents

A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

Hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f.

Structure-activity relationship studies of novel heteroretinoids: Induction of apoptosis in the HL-60 cell line by a novel isoxazole-containing heteroretinoid

In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were not active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the trans structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.