63366-79-0

Basic information

• Product Name: 5-Isoxazolecarboxylicacid,3-methyl-,ethylester(6CI,7CI,9CI)
• Synonyms: 5-Isoxazolecarboxylicacid,3-methyl-,ethylester(6CI,7CI,9CI);5-Isoxazolecarboxylicacid, 3-methyl-, ethyl ester;3-Methyl-5-Isoxazolecarboxylic acid, ethyl ester;3-methylisoxazole-5-carboxylic acid ethyl ester;ethyl 3-methyl-1,2-oxazole-5-carboxylate
• CAS NO: 63366-79-0
• Molecular Formula: C₇H₉NO₃
• Molecular Weight: 155.15
• Product Categories: OXAZOLE
• Mol File: 63366-79-0.mol

Chemical Properties

• Melting Point: 27-28℃
• Boiling Point: 243.3 °C at 760 mmHg
• Flash Point: 100.9 °C
• Appearance: /
• Density: 1.139 g/cm³
• Vapor Pressure: 0.0324mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -3.24±0.50(Predicted)
• CAS DataBase Reference: 5-Isoxazolecarboxylicacid,3-methyl-,ethylester(6CI,7CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isoxazolecarboxylicacid,3-methyl-,ethylester(6CI,7CI,9CI)(63366-79-0)
• EPA Substance Registry System: 5-Isoxazolecarboxylicacid,3-methyl-,ethylester(6CI,7CI,9CI)(63366-79-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 63366-79-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Isoxazolecarboxylic acid, 3-methyl-, ethyl ester (6CI, 7CI, 9CI) is used as a building block for the synthesis of various biologically active compounds in the pharmaceutical industry. Its unique chemical structure and reactivity make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Isoxazolecarboxylic acid, 3-methyl-, ethyl ester (6CI, 7CI, 9CI) is utilized as a key intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its potential applications in this field contribute to the development of more effective and environmentally friendly solutions for crop protection and management.
Used in Chemical Research and Development:
Due to its reactivity and versatility in chemical reactions, 5-Isoxazolecarboxylic acid, 3-methyl-, ethyl ester (6CI, 7CI, 9CI) is also used in chemical research and development. It serves as a valuable starting material for the synthesis of various organic compounds and contributes to the advancement of chemical science and technology.
Used in Industrial Applications:
5-Isoxazolecarboxylic acid, 3-methyl-, ethyl ester (6CI, 7CI, 9CI) may also have some industrial uses due to its reactivity and versatility in chemical reactions. Its potential applications in various industries could lead to the development of new products and processes that benefit from its unique chemical properties.

InChI:InChI=1/C7H9NO3/c1-3-10-7(9)6-4-5(2)8-11-6/h4H,3H2,1-2H3

Upstream product

• 615-79-2 ethyl 2,4-diketopentanoate 
• 105-37-3 Ethyl propionate 
• 4857-42-5 3-methyl-5-isoxazolecarboxylic acid 
• 64-17-5 ethanol 
• 13081-00-0 ethyl-4-hydroximino-2-oxopentanoate 
• 79-24-3 Nitroethane 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 1085-32-1 3-methyl-isoxazole-5-carboxylic acid N'-benzyl-hydrazide 
• 2532-31-2 3-methyl-isoxazole-5-carboxylic acid N'-phenethyl-hydrazide 
• 1219-39-2 3-methyl-isoxazole-5-carboxylic acid N'-(1-phenyl-ethyl)-hydrazide 
• 2532-34-5 3-methyl-isoxazole-5-carboxylic acid N'-(1-methyl-2-phenyl-ethyl)-hydrazide 
• 2532-35-6 3-methyl-isoxazole-5-carboxylic acid N'-(1-methyl-3-phenyl-propyl)-hydrazide 
• 89179-79-3 3-methylisoxazole-5-carbohydrazide 
• 130403-12-2 3-Methyl-isoxazole-5-carboxylic acid (2-isopropyl-6-methyl-phenyl)-amide 
• 130403-05-3 5-(2,6-dimethyl phenylcarbamoyl)-3-methyl isoxazole 
• 145441-11-8 3-Methyl-isoxazole-5-carboxylic acid (2,4,6-trimethyl-phenyl)-amide 
• 4857-42-5 3-methyl-5-isoxazolecarboxylic acid 
• 40340-41-8 5-chloromethyl-3-methylisoxazole 
• 36958-61-9 5-(bromomethyl)-3-methyl-1,2-oxazole 
• 14716-89-3 3-methyl-5-isoxazolemethanol 
• 92547-99-4 3-methyl-isoxazole-5-carboxylic acid (1-methyl-3-phenyl-propylidene)-hydrazide 

Relevant articles and documents

Structure-Based Drug Design of Mineralocorticoid Receptor Antagonists to Explore Oxosteroid Receptor Selectivity

The mineralocorticoid receptor (MR) is a nuclear hormone receptor involved in the regulation of body fluid and electrolyte homeostasis. In this study we explore selectivity triggers for a series of nonsteroidal MR antagonists to improve selectivity over other members of the oxosteroid receptor family. A biaryl sulfonamide compound was identified in a high-throughput screening (HTS) campaign. The compound bound to MR with pKi=6.6, but displayed poor selectivity over the glucocorticoid receptor (GR) and the progesterone receptor (PR). Following X-ray crystallography of MR in complex with the HTS hit, a compound library was designed that explored an induced-fit hypothesis that required movement of the Met852 side chain. An improvement in MR selectivity of 11- to 79-fold over PR and 23- to 234-fold over GR was obtained. Given the U-shaped binding conformation, macrocyclizations were explored, yielding a macrocycle that bound to MR with pKi=7.3. Two protein–ligand X-ray structures were determined, confirming the hypothesized binding mode for the designed compounds.

Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3

A range of isoxazole-containing amino acids was synthesized that displaced acetyl-lysine-containing peptides from the BAZ2A, BRD4(1), and BRD9 bromodomains. Three of these amino acids were incorporated into a histone H4-mimicking peptide and their affinity for BRD4(1) was assessed. Affinities of the isoxazole-containing peptides are comparable to those of a hyperacetylated histone H4-mimicking cognate peptide, and demonstrated a dependence on the position at which the unnatural residue was incorporated. An isoxazole-based alkylating agent was developed to selectively alkylate cysteine residues in situ. Selective monoalkylation of a histone H4-mimicking peptide, containing a lysine to cysteine residue substitution (K12C), resulted in acetyl-lysine mimic incorporation, with high affinity for the BRD4 bromodomain. The same technology was used to alkylate a K18C mutant of histone H3.

HETEROCYCLIC COMPOUND HAVING TYPE I 11 BETA HYDROXYSTEROID DEHYDROGENASE INHIBITORY ACTIVITY

Disclosed is a compound useful as a type I 11 β hydroxysteroid dehydrogenase inhibitor. A compound represented by the formula: a pharmaceutically acceptable salt or solvate thereof, wherein R1 is optionally substituted cycloalkyl, optionally su

PGD2 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES

Disclosed are CRTH2 inhibitors represented by Structural Formula (I). The values for the variables of Structural Formula (I) are provided herein.

A method for generating nitrile oxides from nitroalkanes: A microwave assisted route for isoxazoles

A convenient route has been developed for generation of nitrile oxides in situ from nitroalkanes under very mild conditions using microwave irradiation, using 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) and DMAP as catalyst.

Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: Synthesis and muscarinic activity

A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M1 receptor subtype) and isolated guinea-pig atrium (M2 receptor subtype) and ileum (M3 receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.

New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents

We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2.6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.