3-Amino-5-methylisoxazole

Base Information

• Chemical Name: 3-Amino-5-methylisoxazole
• CAS No.: 1072-67-9
• Deprecated CAS: 1195418-99-5
• Molecular Formula: C4H6N2O
• Molecular Weight: 98.1044
• Hs Code.: 29349990
• European Community (EC) Number: 214-013-6
• NSC Number: 159134
• UNII: G54MJS11L9
• DSSTox Substance ID: DTXSID9021631
• Nikkaji Number: J80.140B
• Wikidata: Q27278772
• Metabolomics Workbench ID: 130612
• ChEMBL ID: CHEMBL3183354
• Mol file: 1072-67-9.mol

Synonyms:3-amino-5-methylisoxazole;3A5MI cpd

Chemical Property of 3-Amino-5-methylisoxazole

Chemical Property:

• Appearance/Colour: slightly yellow flakes
• Vapor Pressure: 0.0487mmHg at 25°C
• Melting Point: 59-63 °C
• Refractive Index: 1.524
• Boiling Point: 235.9 °C at 760 mmHg
• PKA: 2.40±0.10(Predicted)
• Flash Point: 96.5 °C
• PSA: 52.05000
• Density: 1.167 g/cm³
• LogP: 1.14640
• Storage Temp.: Refrigerator
• Solubility.: soluble
• Water Solubility.: soluble
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 98.048012819
• Heavy Atom Count: 7
• Complexity: 66.7

Purity/Quality:

99% ^*data from raw suppliers

3-Amino-5-methylisoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: Xi-F,Xi,F,Xn
• Statements: 5-36/37/38-11-36/37/38/5-20/21/22
• Safety Statements: 22-24/25-47-37/39-26-16-26/37/39/47-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CC1=CC(=NO1)N
• General Description: 3-Amino-5-methylisoxazole is a key intermediate used in the synthesis of novel antimicrobial compounds, particularly spiroisoxazolo[2,3-b][1,2,4]thiadiazole and spiroisoxazolo[2,3-b][1,2,4]oxadiazole derivatives. These compounds exhibit significant antibacterial and antifungal activity, demonstrating potential as effective agents against resistant microbial strains. The structural incorporation of 3-amino-5-methylisoxazole contributes to the bioactivity of these hybrid systems, especially when combined with specific substituents like chloro, methoxy, or bromo groups on the aromatic ring.

Technology Process of 3-Amino-5-methylisoxazole

There total 16 articles about 3-Amino-5-methylisoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.2%

→ 5-methylisoxazol-3-ylamine (1072-67-9)

Guidance literature:

Reference yield: 80.0%

C11H13N3O2S → 5-methylisoxazol-3-ylamine (1072-67-9)

Guidance literature:

C₁₁H₁₃N₃O₂S; With hydroxylamine hydrochloride; potassium carbonate; In water; at 85 ℃; for 2h;

With hydrogenchloride; In water; for 1h;

Reference yield: 77.0%

3-hydroxybutanenitrile (4368-06-3) → 5-methylisoxazol-3-ylamine (1072-67-9)

Guidance literature:

3-hydroxybutanenitrile; With hydroxylamine hydrochloride; potassium carbonate; In water; at 20 - 60 ℃; for 3h;

With iron(III) chloride; In toluene; Reagent/catalyst; Temperature; Reflux;

upstream raw materials:

(5-methyl-isoxazol-3-yl)-carbamic acid benzyl ester

(5-methyl-isoxazol-3-yl)-carbamic acid ethyl ester

but-2-enenitrile

(Z)-4-(5-Methyl-isoxazol-3-ylamino)-pent-3-en-2-one

Downstream raw materials:

N-(5-methyl-3-isoxazolyl)acetamide

N-acetylsulfamethoxazole

5-methyl-3-[3-(4-nitro-phenyl)-triazenyl]-isoxazole

5-methyl-3-[3-(3-nitro-phenyl)-triazenyl]-isoxazole

Refernces

Design, synthesis, and antimicrobial activity of novel spiroisoxazolo[2,3- b[[1,2,4]thiadiazole-2,2-thiazolidine-4-ones and spiroisoxazolo[2,3-b[[1,2,4] oxadiazole-2, 2-thiazolidine-4-ones

10.1080/17415993.2012.703671

The research explores the development of new antimicrobial compounds. The study aims to address the increasing resistance of bacteria and fungi to existing antimicrobial agents by synthesizing and evaluating the antimicrobial activity of novel spiroisoxazolo[2,3-b][1,2,4]thiadiazole-2,2′-thiazolidine-4′-ones (9a–9e) and spiroisoxazolo[2,3-b][1,2,4]oxadiazole-2,2′-thiazolidine-4′-ones (12a–12e). The synthesis involved key chemicals such as 3-amino-5-methylisoxazole, aryl isothiocyanates, aryl isocyanates, and mercaptoacetic acid. The compounds were tested for their antibacterial and antifungal activities against various bacterial and fungal strains, showing significant antimicrobial activity compared to standard drugs like Cipro?oxacin and Clotrimazole. The study concludes that these novel compounds, featuring isoxazole–thiadiazole–thiazolidone and isoxazole–oxadiazole–thiazolidone ring systems, have promising potential as new antimicrobial agents, particularly those with specific substituents on the benzene ring, such as chloro, methoxy, and bromo groups.