Ethyl 5-(thiophen-2-YL)isoxazole-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-(thiophen-2-YL)isoxazole-3-carboxylate
• CAS No.: 90924-54-2
• Molecular Formula: C₁₀H₉NO₃S
• Molecular Weight: 223.252
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60372553
• Nikkaji Number: J1.682.961G
• Wikidata: Q82160329
• Mol file: 90924-54-2.mol

Synonyms:90924-54-2;ETHYL 5-(THIOPHEN-2-YL)ISOXAZOLE-3-CARBOXYLATE;ethyl 5-thiophen-2-yl-1,2-oxazole-3-carboxylate;Ethyl 5-(2-thienyl)isoxazole-3-carboxylate;ethyl 5-(thiophen-2-yl)-1,2-oxazole-3-carboxylate;ethyl 5-thien-2-ylisoxazole-3-carboxylate;Maybridge3_007199;SCHEMBL508571;DTXSID60372553;HMS1451H05;CCG-53531;MFCD02090509;AKOS003673451;AS-9326;SB23045;IDI1_018586;ethyl 5-(2-thienyl)-3-isoxazolecarboxylate;CS-0055012;E1286;FT-0708744;C77094;A860659;SR-01000642691-1;3-Isoxazolecarboxylicacid,5-(2-thienyl)-,ethyl ester;5-(2-Thienyl)-3-isoxazolecarboxylic acid ethyl ester;3-Isoxazolecarboxylic acid, 5-(2-thienyl)-, ethyl ester;Ethyl 5-(thiophen-2-yl)isoxazole-3-carboxylate, AldrichCPR

Chemical Property of Ethyl 5-(thiophen-2-YL)isoxazole-3-carboxylate

Chemical Property:

• Vapor Pressure: 5.75E-06mmHg at 25°C
• Melting Point: 47.5-51.5°C
• Refractive Index: 1.554
• Boiling Point: 379.7 °C at 760 mmHg
• Flash Point: 183.4 °C
• PSA: 80.57000
• Density: 1.278g/cm³
• LogP: 2.57980
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 223.03031432
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 5-(Thiophen-2-yl)isoxazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NOC(=C1)C2=CC=CS2
• Uses: Ethyl 5-(thiophen-2-yl)isoxazole-3-carboxylate is a useful reagent for organic synthesis.

Technology Process of Ethyl 5-(thiophen-2-YL)isoxazole-3-carboxylate

There total 8 articles about Ethyl 5-(thiophen-2-YL)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: 90.0%

(Z)-ethyl 2-hydroxy-4-oxo-4-(thiophen-2-yl)but-2-enoate (785732-30-1) → ethyl 5-(2-thiophenyl)-isoxazole-3-carboxylate (90924-54-2)

Guidance literature:

With hydroxylamine hydrochloride; In acetonitrile; at 70 ℃; for 3h;

DOI:10.1021/acs.joc.9b03399

Reference yield: 77.0%

2-ethynyl-thiophene (4298-52-6) + glycine ethyl ester hydrochloride (623-33-6) → ethyl 5-(2-thiophenyl)-isoxazole-3-carboxylate (90924-54-2)

Guidance literature:

With tert.-butylnitrite; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; zinc dibromide; In tert-butyl methyl ether; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c02281

Reference yield: 36.0%

ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) + 2-thienylcarbonyloxymethyl-Wang resin → ethyl 5-(2-thiophenyl)-isoxazole-3-carboxylate (90924-54-2)

Guidance literature:

2-thienylcarbonyloxymethyl-Wang resin; Tebbe reagent; In tetrahydrofuran; at 25 ℃; for 16h;

ethyl 2-chloro-2-(hydroxyimino)acetate; With triethylamine; In tetrahydrofuran;

With trifluoroacetic acid; In dichloromethane; at 25 ℃; Further stages.;

DOI:10.1021/ol016479x

upstream raw materials:

2-hydroxyimino-4-oxo-4-thiophen-2-yl-butyric acid ethyl ester

ethyl 2-chloro-2-(hydroxyimino)acetate

2-Acetylthiophene

2-Acetyl-5-bromothiophene

Downstream raw materials:

5-(2-thienyl)isoxazole-3-carbaldehyde

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

5-(2-Thienyl)-3-isoxazolcarbonsaeure-hydrazid

N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide

Refernces

• 1、 -. "ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF". . . Retrieved 2020/04/25.
• 2、 -. "ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF". . . Retrieved 2018/10/19.