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

Chemical Properties

yellow to orange-brown crystalline powder

Uses

5-Amino-3-methylisoxazole is a widely used reactant. 5-Amino-3-methylisoxazole has been used as a reactant for the preparation of heterocycle fused pyridinecarboxylic acids.

General Description

5-Amino-3-methylisoxazole reacts with α,β-unsaturated ketones to yield the corresponding isoxazolo[5,4-b]pyridines.

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.