20328-15-8

Basic information

• Product Name: ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE
• Synonyms: ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE;3-Methylisoxazole-4-carboxylic acid ethyl ester;4-Isoxazolecarboxylicacid,3-methyl-,ethylester(8CI,9CI)
• CAS NO: 20328-15-8
• Molecular Formula: C₇H₉NO₃
• Molecular Weight: 155.15
• EINECS: -0
• Product Categories: OXAZOLE
• Mol File: 20328-15-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 64°C 0,6mm
• Flash Point: 64°C/0.6mm
• Appearance: /
• Density: 1.139 g/cm³
• Vapor Pressure: 0.082mmHg at 25°C
• Refractive Index: 1.4590
• Storage Temp.: 2-8°C
• PKA: -3.24±0.50(Predicted)
• BRN: 1072756
• CAS DataBase Reference: ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE(20328-15-8)
• EPA Substance Registry System: ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE(20328-15-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 20328-15-8(Hazardous Substances Data)

Usage

Description

ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE, also known as 3-Methylisoxazole-4-carboxylic Acid Ethyl Ester, is an organic compound that is primarily recognized as an impurity in Leflunomide (L322750). ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE is characterized by its isoxazole ring structure and ester functional group, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE is used as an impurity in the immunosuppressive drug Leflunomide (L322750) for its role in inhibiting the proliferation of T and B cells. This application is significant in the treatment of autoimmune diseases and transplantation medicine, where the suppression of immune responses is crucial.
As an impurity in Leflunomide, ETHYL 3-METHYLISOXAZOLE-4-CARBOXYLATE may also be subject to regulatory controls and quality assessments to ensure the safety and efficacy of the final drug product. The presence of this compound in Leflunomide highlights the importance of understanding and managing impurities in the pharmaceutical development process.

Synthesis Reference(s)

Synthesis, p. 792, 1985 DOI: 10.1055/s-1985-31353

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

Upstream product

• 25388-15-2 3-methyl-5-[N'-(toluene-4-sulfonyl)-hydrazino]-isoxazole-4-carboxylic acid ethyl ester 
• 79-24-3 Nitroethane 
• 53927-12-1 ethyl-3-(pyrrolidin-1-yl)prop-2-enoate 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 3356-94-3 ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate 
• 25388-05-0 5-hydrazino-3-methyl-isoxazole-4-carboxylic acid ethyl ester 
• 123-75-1 pyrrolidine 
• 65651-80-1 ethyl (E)-3-(pyrrolidin-1-yl)acrylate 
• 103-72-0 phenyl isothiocyanate 
• 623-47-2 propynoic acid ethyl ester 
• 25786-72-5 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester 

Downstream Products

• 17153-20-7 3-methyl isoxazole-4-carboxylic acid 
• 92248-58-3 ethyl 3-methyl-5-(4-tolyl)isoxazole-4-carboxylate 

Relevant articles and documents

Studies on the deamination of the ethyl ester of 5-amino-3-methylisoxazole- 4-carboxylic Acid

The unusual behavior of the ethyl ester of 5-amino-3-methylisoxazole-4- carboxylic acid (1) during deamination is described. Possible explanations for the anomalies of the diazotization reaction are proposed. Deamination methods leading to ethyl ester of 3-methylisoxazole-4-carboxylic acid (5) are presented. 5 will serve as a lead compound for a new series of immunomodulatory agents.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. X. Synthesis of 5-Substituted Ethyl or Methyl 4-Isoxazolecarboxylates and Methyl 4-(2,2-Dimethyl-1-oxopropyl)-5-isoxazolecarboxylate

Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with hydroxylamine hydrochloride in methanol solution afforded in high yields the relative esters of 5-substituted 4-isoxazolecarboxylic acids II.These esters were hydrolyzed generally with concentrated hydrochloric acid-acetic acid mixtures to the corresponding carboxylic acids in satisfactory yields.Ethyl or methyl esters II isomerized with sodium ethoxide or methoxide, respectively, to the corresponding esters or hemiesters of 2-cyano-3-oxoalkanoic acids generally in excellent to satisfactory yields.Reaction of methyl 5,5-dimethyl-3-dimethylaminomethylene-2,4-dioxohexanoate with hydroxylamine hydrochloride afforded in moderate yield methyl 4-(2,2-dimethyl-1-oxopropyl)-5-isoxazolecarboxylate, which was converted by acid hydrolysis as above to 4-t-butyl-4-hydroxyfuroisoxazol-6-(4H)-one.