3-(2-Methoxy-phenyl)-isoxazole-5-carbaldehyde

Base Information

• Chemical Name: 3-(2-Methoxy-phenyl)-isoxazole-5-carbaldehyde
• CAS No.: 808740-33-2
• Molecular Formula: C11H9 N O3
• Molecular Weight: 203.197
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40695994
• Wikidata: Q82625392
• Mol file: 808740-33-2.mol

Synonyms:808740-33-2;3-(2-METHOXY-PHENYL)-ISOXAZOLE-5-CARBALDEHYDE;3-(2-Methoxyphenyl)isoxazole-5-carbaldehyde;3-(2-methoxyphenyl)-1,2-oxazole-5-carbaldehyde;SCHEMBL20507148;DTXSID40695994;MFCD06738522;AKOS022359646;AB27305;CS-0331018;FT-0716327;A864636;3-(2-Methoxyphenyl)isoxazole-5-carbaldehyde, AldrichCPR

Chemical Property of 3-(2-Methoxy-phenyl)-isoxazole-5-carbaldehyde

Chemical Property:

• PSA: 52.33000
• LogP: 2.16270
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

98%min ^*data from raw suppliers

3-(2-Methoxyphenyl)isoxazole-5-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1C2=NOC(=C2)C=O

Technology Process of 3-(2-Methoxy-phenyl)-isoxazole-5-carbaldehyde

There total 4 articles about 3-(2-Methoxy-phenyl)-isoxazole-5-carbaldehyde 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: 76.0%

5-hydroxymethyl-3-(o-methoxyphenyl)isoxazole (345967-78-4) → 3-(2-methoxyphenyl)-isoxazole-5-carbaldehyde (808740-33-2)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.5012/bkcs.2011.32.7.2449

Reference yield:

2-Methoxy-benzaldehyde oxime (29577-53-5) → 3-(2-methoxyphenyl)-isoxazole-5-carbaldehyde (808740-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-chlorosuccinimide; pyridine / tetrahydrofuran / 0.5 h / 60 °C

1.2: triethylamine / tetrahydrofuran / 2 h / 50 °C

2.1: pyridinium chlorochromate; silica gel / CH₂Cl₂ / 5 h

With pyridine; N-chloro-succinimide; silica gel; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2004.06.011

Reference yield:

ortho-anisaldehyde (135-02-4) → 3-(2-methoxyphenyl)-isoxazole-5-carbaldehyde (808740-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 20 °C

2.1: pyridine; N-chloro-succinimide / tetrahydrofuran / 1 h / 20 - 60 °C / Inert atmosphere

2.2: 3 h / 50 °C / Inert atmosphere

3.1: silica gel; pyridinium chlorochromate / dichloromethane / 6 h / 20 °C

With pyridine; N-chloro-succinimide; silica gel; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.5012/bkcs.2011.32.7.2449

upstream raw materials:

5-hydroxymethyl-3-(o-methoxyphenyl)isoxazole

2-Methoxy-benzaldehyde oxime

ortho-anisaldehyde

Downstream raw materials:

C₂₇H₃₃ClN₄O₂

C₂₇H₃₄N₄O₂

C₂₇H₃₃FN₄O₂

Refernces

• 1、 Zhang, Dawei,Chen, Xiaodong,Guo, Xue,Zhang, Yumin,Hou, Yaya,Zhao, Tianqi,Gu, Qiang. "An efficient solvent-free synthesis of isoxazolyl-1,4-dihydropyridines on solid support SiO2 under microwave irradiation". . p. 1605 - 1614. Retrieved 2016/08/16.
• 2、 Landge, Kamalkishor P.,Oh, Ji Seon,Pae, Ae Nim,Park, Woo Kyu,Gong, Jae Yang,Koh, Hun Yeong,Jung, Sun Ho. "Synthesis and biological evaluation of focused isoxazolylpiperidinylpiperazine Library for dopamine D3 and D 4 Receptor antagonists". experimental part. p. 2449 - 2452. Retrieved 2012/06/01.