Methyl 5-(2-thienyl)isoxazole-3-carboxylate

Base Information

• Chemical Name: Methyl 5-(2-thienyl)isoxazole-3-carboxylate
• CAS No.: 517870-23-4
• Molecular Formula: C₉H₇NO₃S
• Molecular Weight: 209.225
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90361394
• Wikidata: Q82143720
• Mol file: 517870-23-4.mol

Synonyms:517870-23-4;methyl 5-(2-thienyl)isoxazole-3-carboxylate;methyl 5-(thiophen-2-yl)isoxazole-3-carboxylate;methyl 5-thiophen-2-yl-1,2-oxazole-3-carboxylate;5-THIOPHEN-2-YL-ISOXAZOLE-3-CARBOXYLIC ACID METHYL ESTER;methyl 5-(thiophen-2-yl)-1,2-oxazole-3-carboxylate;MFCD03778976;SCHEMBL20507129;DTXSID90361394;HMS1600D03;BBL022353;STK691841;AKOS003314440;CCG-311912;DS-17345;SY015178;CS-0072038;FT-0724140;methyl 5-(2-thienyl)-3-isoxazolecarboxylate;EN300-154429;methyl5-(thiophen-2-yl)isoxazole-3-carboxylate;A871182;5-Thiophen-2-ylisoxazole-3-carboxylic acid methyl ester;F2161-0008;Methyl 5-(thiophen-2-yl)isoxazole-3-carboxylate, AldrichCPR

Chemical Property of Methyl 5-(2-thienyl)isoxazole-3-carboxylate

Chemical Property:

• Boiling Point: 371.3±32.0 °C(Predicted)
• PKA: -5.88±0.50(Predicted)
• PSA: 80.57000
• Density: 1.323±0.06 g/cm3(Predicted)
• LogP: 2.18970
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 209.01466426
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

95% ^*data from raw suppliers

Methyl5-(2-Thienyl)isoxazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NOC(=C1)C2=CC=CS2

Technology Process of Methyl 5-(2-thienyl)isoxazole-3-carboxylate

There total 2 articles about Methyl 5-(2-thienyl)isoxazole-3-carboxylate 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: 83.21%

methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate (57409-51-5) → 5-(2-thienyl)-3-isoxazolecarboxylic acid methyl ester (517870-23-4)

Guidance literature:

With hydroxylamine hydrochloride; In methanol; at 50 ℃; for 2h;

Reference yield:

2-Acetylthiophene (88-15-3,97511-16-5) → 5-(2-thienyl)-3-isoxazolecarboxylic acid methyl ester (517870-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / toluene; tetrahydrofuran / 20 °C

2: hydroxylamine hydrochloride / methanol / 6 h / 50 °C

With hydroxylamine hydrochloride; potassium tert-butylate; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/j.ejmech.2019.111635

Reference yield: 82.0%

5-(2-thienyl)-3-isoxazolecarboxylic acid methyl ester (517870-23-4) → [5-(2-thienyl)isoxazol-3-yl]methanol (194491-44-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 50 ℃; for 5h;

DOI:10.1016/j.ejmech.2019.111635

upstream raw materials:

methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate

2-Acetylthiophene

Downstream raw materials:

N-phenyl-5-(thiophen-2-yl)isoxazol-3-carboxamide

[5-(2-thienyl)isoxazol-3-yl]methanol

Refernces

• 1、 Veeraswamy,Kurumurthy,Santhosh Kumar,Sambasiva Rao,Thelakkat, Kavya,Kotamraju, Srigiridhar,Narsaiah. "Synthesis of novel 5-substituted isoxazole-3-carboxamide derivatives and cytotoxicity studies on lung cancer cell line". . p. 1369 - 1375. Retrieved 2012/11/13.