Methyl 3-hydroxyisoxazole-5-carboxylate

Base Information

• Chemical Name: Methyl 3-hydroxyisoxazole-5-carboxylate
• CAS No.: 10068-07-2
• Molecular Formula: C5H5NO4
• Molecular Weight: 143.099
• Hs Code.: 29349990
• European Community (EC) Number: 628-550-2
• DSSTox Substance ID: DTXSID10369170
• Nikkaji Number: J942.595K
• Wikidata: Q72491339
• Mol file: 10068-07-2.mol

Synonyms:Methyl 3-hydroxyisoxazole-5-carboxylate;10068-07-2;Methyl 3-hydroxy-5-isoxazolecarboxylate;methyl 3-hydroxy-1,2-oxazole-5-carboxylate;methyl 3-oxo-1,2-oxazole-5-carboxylate;Methyl 3-hydroxyl-5-isoxazolecarboxylate;5-Isoxazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester;MFCD00062870;3-Hydroxyisoxazole-5-carboxylic Acid Methyl Ester;METHYL-3-HYDROXY-5-ISOXAZOLECARBOXYLATE;3-hydroxy-isoxazole-5-carboxylic acid methyl ester;SCHEMBL444734;methyl 3-oxo-2,3-dihydro-1,2-oxazole-5-carboxylate;DTXSID10369170;STK503447;AKOS005171519;AKOS025395603;CS-W000792;Methyl 3-hydroxy-5-isoxazole carboxylate;methyl 3-hydroxy-isoxazole-5-carboxylate;AC-31015;SY032405;TS-00046;AM20070655;BB 0260331;FT-0628562;M2441;Methyl 3-hydroxy-5-isoxazolecarboxylate, 98%;UPCMLD00X10068-07-2:001;UPCMLD00X10068-07-2:002;EN300-104012;F2199-0064;3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester

Chemical Property of Methyl 3-hydroxyisoxazole-5-carboxylate

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 7.31E-05mmHg at 25°C
• Melting Point: 160-163 °C(lit.)
• Refractive Index: 1.494
• Boiling Point: 332.915 °C at 760 mmHg
• PKA: 11.25±0.40(Predicted)
• Flash Point: 155.142 °C
• PSA: 72.56000
• Density: 1.406 g/cm³
• LogP: 0.16680
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Ethanol, Ether, Ethyl Acetate, Methanol
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 143.02185764
• Heavy Atom Count: 10
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-Hydroxyisoxazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC(=O)NO1
• Uses: An interesting intermediate Methyl 3-hydroxy-5-isoxazolecarboxylate was used in the enantioselective synthesis of a key precursor to the tetracycline antibiotics. It was also used in the preparation of formamidinopiperidine analog, an N-amidinopiperidine compound.

Technology Process of Methyl 3-hydroxyisoxazole-5-carboxylate

There total 18 articles about Methyl 3-hydroxyisoxazole-5-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: 98.0%

3-benzyloxyisoxazole-5-carboxylic acid methyl ester (205115-22-6) → methyl 3-hydroxy-5-isoxazolecarboxylate (10068-07-2)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h; Heating;

DOI:10.1002/(SICI)1099-0690(199803)1998:3<473::AID-EJOC473>3.0.CO;2-V

Reference yield: 96.0%

2-Benzyl-3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (205115-33-9) → methyl 3-hydroxy-5-isoxazolecarboxylate (10068-07-2)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h; Heating;

DOI:10.1002/(SICI)1099-0690(199803)1998:3<473::AID-EJOC473>3.0.CO;2-V

Reference yield: 92.0%

dimethyl acetylenedicarboxylate (762-42-5) → methyl 3-hydroxy-5-isoxazolecarboxylate (10068-07-2)

Guidance literature:

dimethyl acetylenedicarboxylate; With N-hydroxyurea; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 0 ℃; for 1h;

With hydrogenchloride; In methanol; water;

DOI:10.1021/acs.jmedchem.9b00739

upstream raw materials:

methanol

3-hydroxy-5-isoxazole hydroxamic acid

dimethyl 2-bromofumarate

N-hydroxyurea

Downstream raw materials:

3-methoxyisoxazole-5-carboxylic acid methyl ester

methyl 3-isopropoxyisoxazole-5-carboxylate

Methyl 3-[3-(tert-butyloxycarbonylamino)propyloxy]-5-isoxazolecarboxylate

3-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester

Refernces

• 1、 Yang, Kan,Yu, Jinying,Nong, Keyi,Wang, Youzhi,Niu, Ao,Chen, Wenlu,Dong, Jibin,Wang, Jinxin. "Discovery of Potent, Selective, and Direct Acid Sphingomyelinase Inhibitors with Antidepressant Activity". . p. 961 - 974. Retrieved 2020.
• 2、 -. "Alkoxy isoxazole derivative as well as preparation method and application thereof (by machine translation)". Paragraph 0106-0108. . Retrieved 2020/08/27.