14678-02-5

Basic information

• Product Name: 5-AMINO-3-METHYLISOXAZOLE
• Synonyms: 3-methyl-5-isoxazolamin;3-Methyl-5-isoxazolamine;5-Isoxazolamine, 3-methyl-;3-METHYLISOXAZOL-5-AMINE;3-METHYL-ISOXAZOL-5-YLAMINE;5-AMINO-3-METHYLISOXAZOLE;AKOS PAO-1620;BUTTPARK 94\04-02
• CAS NO: 14678-02-5
• Molecular Formula: C₄H₆N₂O
• Molecular Weight: 98.1
• EINECS: 238-719-9
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Isoxazoles
• Mol File: 14678-02-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 231.3±20.0℃ (760 Torr)
• Flash Point: 93.7±21.8℃
• Appearance: Yellow to orange-brown/Crystalline Powder and Chunks
• Density: 1.167±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0629mmHg at 25°C
• Refractive Index: 1.4327 (estimate)
• Storage Temp.: Keep Cold
• Solubility: Chloroform, Methanol (Slightly)
• PKA: -0.59±0.50(Predicted)
• BRN: 107906
• CAS DataBase Reference: 5-AMINO-3-METHYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-3-METHYLISOXAZOLE(14678-02-5)
• EPA Substance Registry System: 5-AMINO-3-METHYLISOXAZOLE(14678-02-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• HazardClass: KEEP COLD
• Hazardous Substances Data: 14678-02-5(Hazardous Substances Data)

Usage

Description

5-Amino-3-methylisoxazole is a yellow to orange-brown crystalline powder that is known for its reactivity with α,β-unsaturated ketones, leading to the formation of isoxazolo[5,4-b]pyridines. 5-AMINO-3-METHYLISOXAZOLE is a widely used reactant in various chemical processes and has demonstrated its utility in the synthesis of complex organic molecules.

Uses

Used in Pharmaceutical Industry:
5-Amino-3-methylisoxazole is used as a reactant for the preparation of heterocycle fused pyridinecarboxylic acids, which are important in the development of pharmaceutical compounds. These heterocycle fused pyridines have potential applications in the treatment of various diseases due to their unique chemical structures and properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Amino-3-methylisoxazole serves as a versatile building block for the creation of complex organic molecules. Its reactivity with α,β-unsaturated ketones allows for the formation of isoxazolo[5,4-b]pyridines, which can be further modified and utilized in the synthesis of a wide range of compounds with diverse applications.
Used in Research and Development:
5-Amino-3-methylisoxazole is also used in research and development laboratories for the study of its chemical properties and potential applications. Its reactivity and the ability to form isoxazolo[5,4-b]pyridines make it an interesting compound for scientists to explore and develop new methodologies and applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C4H6N2O/c1-3-2-4(5)7-6-3/h2H,5H2,1H3

Upstream product

• 84661-50-7 5-amino-3-methyl-1,2-oxazole-4-carboxylic acid 
• 1001-56-5 buta-2,3-dienenitrile 
• 13752-78-8 2-butynenitrile 
• 1118-61-2 3-Aminocrotononitrile 
• 7732-18-5 water 
• 7803-49-8 hydroxylamine 
• 870-64-4 2-aminocrotononitrile 
• 141-78-6 ethyl acetate 
• 75-05-8 acetonitrile 
• 2469-99-0 Cyanoaceton 

Downstream Products

• 55622-09-8 5-amino-3-methyl-4-phenylazoisoxazole 
• 17103-52-5 4-amino-N-(3-methyl-1,2-oxazol-5-yl)benzene-1-sulfonamide 
• 71565-73-6 N-(4-methoxy-phenyl)-N'-(3-methyl-isoxazol-5-yl)-sulfamide 
• 41230-50-6 5-Acetamido-3-methyl-4-nitroisoxazol 
• 41230-59-5 ethyl 2-((3-methylisoxazol-5-yl)amino)-2-oxoacetate 
• 54108-13-3 N-(3-methyl-isoxazol-5-yl)-2-nitro-benzamide 
• 71224-82-3 5-(2-Formylpropenylamino)-3-methylisoxazol 
• 71224-70-9 5-Ethyl-3-methyl-isoxazolo<5,4-b>pyridin 
• 88786-19-0 5-Amino-3-methyl-4-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-isoxazole 
• 142362-78-5 3-methyl-5-<2-(2-propenyloxy)benzylideneamino>isoxazole 
• 118385-14-1 3-Methyl-4,6-diphenyl-isoxazolo[5,4-b]pyridine-5-carbonitrile 
• 118385-13-0 4-Amino-3-methyl-6-phenyl-isoxazolo[5,4-b]pyridine-5-carbonitrile 
• 144486-01-1 5-Methyl-N-(3-methyl-isoxazol-5-yl)-2-nitro-benzamide 
• 95199-72-7 ethyl 3,6-dimethyl-4-phenyl-4,7-dihydroisoxazolo<5,4-b>pyridine-5-carboxylate 

Relevant articles and documents

Reactions of N,N-bis(siloxy)enamines with trimethylsilyl cyanide: Aliphatic nitro compounds as convenient precursors of 5-aminoisoxazoles

A convenient procedure was developed for the synthesis of 5-aminoisoxazoles by the consecutive double silylation and cyanation of aliphatic nitro compounds.

An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived: N -Boc ketimines

By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural analysis and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity. This journal is

Approach to the library of fused pyridine-4-carboxylic acids by combes-type reaction of acyl pyruvates and electron-rich amino heterocycles

A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.