23012-17-1

Basic information

• Product Name: 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID
• Synonyms: 2-Methyloxazole-4-carboxylic acid 97%;2-METHYLISOXAZOLE-4-CARBOXYLIC ACID;4-Oxazolecarboxylic acid, 2-methyl-;4-Carboxy-2-methyl-1,3-oxazole
• CAS NO: 23012-17-1
• Molecular Formula: C₅H₅NO₃
• Molecular Weight: 129.11398
• Mol File: 23012-17-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 182-187℃
• Boiling Point: 269.9±13.0 °C(Predicted)
• Appearance: /
• Density: 1.348±0.06 g/cm3(Predicted)
• Refractive Index: 1.536
• Storage Temp.: 2-8°C
• PKA: 3.46±0.10(Predicted)
• CAS DataBase Reference: 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID(23012-17-1)
• EPA Substance Registry System: 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID(23012-17-1)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 23012-17-1(Hazardous Substances Data)

Usage

Description

2-METHYLISOXAZOLE-4-CARBOXYLIC ACID is an organic compound with the molecular formula C5H5NO3. It is a derivative of isoxazole, featuring a methyl group and a carboxylic acid functional group. 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
2-METHYLISOXAZOLE-4-CARBOXYLIC ACID is used as a reactant for the solid-phase preparation of (heteroaryl)carbonyl-substituted dipeptides. These dipeptides act as human protease activated receptor 2 (PAR2) agonists, which have potential applications in the treatment of various diseases, including inflammation and pain.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-METHYLISOXAZOLE-4-CARBOXYLIC ACID is used as a reactant in Pd-catalyzed decarboxylative C-H cross-coupling reactions. This process allows for the formation of new carbon-carbon bonds, which are essential in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Medicinal Chemistry:
2-METHYLISOXAZOLE-4-CARBOXYLIC ACID is also used as a reactant in the stereoselective preparation of 3-amino-N-(phenylsulfonyl)alanines. These compounds serve as inhibitors of ανβ3 integrin, a protein involved in various cellular processes, including cell adhesion and migration. Inhibiting ανβ3 integrin has potential therapeutic applications in the treatment of diseases such as cancer, where cell adhesion and migration play a crucial role in tumor growth and metastasis.

InChI:InChI=1/C5H7NO3/c1-6-2-4(3-9-6)5(7)8/h3H,2H2,1H3,(H,7,8)

Upstream product

• 85806-67-3 2-methyl-oxazole-4-carboxylic acid methyl ester 
• 68683-04-5 ethyl (2-methyl-2-oxazolin-4-yl)carboxylate 
• 141029-63-2 2-methyloxazoline-4-carboxylic acid methyl ester 
• 153180-10-0 Dimethyl acetamido<(phenylthio)methyl>malonate 
• 61999-29-9 2-Methyl-4,5-dihydro-1,3-oxazole-4-carboxylic acid ethyl ester 
• 74-88-4 methyl iodide 
• 10200-43-8 2-methyl-4-carbethoxy-1,3-oxazole 
• 155884-28-9 4,5-dihydro-2-methyl-oxazole-4-carboxylic acid methyl ester 
• 4546-95-6 1H-1,2,3-triazole-4,5-dicarboxylic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 60053-07-8 2-methyl-1-phenyl-1H-imidazole 
• 23012-10-4 2-methyl-2-oxazoline 
• 693-98-1 2-methylimidazole 
• 1005784-90-6 N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-2-methyl-1,3-oxazole-4-carboxamide 
• 875553-59-6 N-methoxy-N-methyl-2-methyloxazole-4-carboxamide 
• 113732-84-6 2-methyl-1,3-oxazole-4-carbaldehyde 

Relevant articles and documents

Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks

An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross-coupling reaction under parallel synthesis conditions.

POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS

The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

Large-scale preparation of 2-methyloxazole-4-carboxaldehyde

The large-scale preparation of 2-methyloxazole-4-carboxaldehyde presents a significant challenge due to the physical characteristics of the molecule. A method for the preparation of 10-kg batches of 2-methyloxazole-4-carboxaldehyde is described. The key reaction is the reduction of the corresponding N-methoxy-N-methyl amide using lithium aluminium hydride, followed by workup and isolation by crystallization.