13999-39-8

Basic information

• Product Name: 3-Amino-4,5-dimethylisoxazole
• Synonyms: 3-amino-4,5-dimethylisoxazole;4,5-dimethyl-1,2-oxazol-3-amine;4,5-Dimethylisoxazol-3-amine;3-AMINO-4,5-DIMETHYLISOXAZOLE 98%;(4,5-dimethylisoxazol-3-yl)amine;4,5-Dimethyl-3-aminoisoxazole;3-IsoxazolaMine, 4,5-diMethyl-;4,5-Dimethyl-3-isoxazolamine
• CAS NO: 13999-39-8
• Molecular Formula: C₅H₈N₂O
• Molecular Weight: 112.12982
• EINECS: 237-802-7
• Mol File: 13999-39-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 115-117 °C
• Boiling Point: 249.974 °C at 760 mmHg
• Flash Point: 104.981 °C
• Appearance: /
• Density: 1.118 g/cm³
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.26±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-4,5-dimethylisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4,5-dimethylisoxazole(13999-39-8)
• EPA Substance Registry System: 3-Amino-4,5-dimethylisoxazole(13999-39-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 13999-39-8(Hazardous Substances Data)

Usage

Description

3-Amino-4,5-dimethylisoxazole is an isoxazole derivative characterized by the presence of an amino group at the 3rd position and two methyl groups at the 4th and 5th positions. It is a versatile compound that serves as a key building block in the synthesis of various biologically active molecules.

Uses

Used in Pharmaceutical Industry:
3-Amino-4,5-dimethylisoxazole is used as a synthetic intermediate for the preparation of a variety of biologically active compounds, particularly selective ETA receptor antagonists. These antagonists play a crucial role in the development of medications targeting conditions such as hypertension, heart failure, and pulmonary arterial hypertension.
Used in Chemical Research:
In addition to its pharmaceutical applications, 3-Amino-4,5-dimethylisoxazole is also utilized in chemical research as a valuable starting material for the synthesis of other complex organic molecules with potential applications in various fields, including materials science, agrochemistry, and environmental science.

InChI:InChI=1/C5H8N2O/c1-3-4(2)8-7-5(3)6/h1-2H3,(H2,6,7)

Upstream product

• 174078-98-9 DIV₀₁₃₈₉ 
• 474713-25-2 2-(β-ethylenedioxyaceto)propionamideoxime 
• 85554-83-2 2,3-dibromo-2-methylbutanenitrile 

Downstream Products

• 195447-72-4 N-(4,5-dimethyl-3-isoxazolyl)-2-bromobenzenesulfonamide 
• 210891-04-6 Edonentan 
• 23256-23-7 Isosulfafurazole 
• 948573-59-9 N-(4,5-dimethylisoxazol-3-yl)-2-(4-benzyloxy-2-methoxyphenyl)acetamide 
• 1190843-59-4 phenyl (4,5-dimethylisoxazol-3-yl)carbamate 
• 254740-64-2 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl) [1,1'-biphenyl]-2-sulfonamide 

Relevant articles and documents

Practical synthesis of 3-amino-4,5-dimethylisoxazole from 2-methyl-2-butenenitrile and acetohydroxamic acid

3-Amino-4,5-dimethylisoxazole was prepared from technicalgrade 2-methyl-2-butenenitrile and acetohydroxamic acid in a 62% overall yield on a multimole scale. The key features of this synthesis are (1) DBU treatment of the technical-grade nitrile mixture to provide a starting material of acceptable purity and (2) use of acetohydroxamic acid as an N-protected hydroxylamine equivalent. This operationally simple method provides the title compound in reasonable overall yield and free of contamination from the isomeric 5-amino-3,4-dimethylisoxazole.

Discovery and synthesis of a potent sulfonamide ET(B) selective antagonist

The synthesis and structure-activity relationships of a series of sulfonamide endothelin antagonists are described. In the course of our modification studies, we discovered ET(B) selective antagonists. The most potent compound 15f displays IC50 values of 1.7 μM and 0.002 μM to ET(A) and ET(B) receptors, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.