5-Methylisoxazole-3-carboxylic acid

Base Information

• Chemical Name: 5-Methylisoxazole-3-carboxylic acid
• CAS No.: 3405-77-4
• Molecular Formula: C5H5NO3
• Molecular Weight: 127.1
• Hs Code.: 29339900
• European Community (EC) Number: 222-289-4
• UNII: YZP807C30G
• DSSTox Substance ID: DTXSID10878772
• Nikkaji Number: J24.399J
• Wikidata: Q27449789
• Mol file: 3405-77-4.mol

Synonyms:5-Methylisoxazole-3-carboxylic acid;3405-77-4;5-methyl-1,2-oxazole-3-carboxylic acid;3-ISOXAZOLECARBOXYLIC ACID, 5-METHYL-;3-CARBOXY-5-METHYLISOXAZOLE;MFCD01318162;1267623-84-6;YZP807C30G;5-methyl-3-isoxazolecarboxylic acid;EINECS 222-289-4;5-methylisoxazole-3-carboxylicacid;5-Methylisoxazole-3-carboxylic-d4 Acid;UNII-YZP807C30G;SCHEMBL286771;5-methylisoxazol-3-carbonsaure;5-methylisoxazole carboxylic acid;DTXSID10878772;5-methyl-isoxazole-carboxylic acid;HMS1754B06;5-methyl-3-isoxazolecarboxlic acid;STR04361;BBL015822;STK260850;5-methyl-isoxazole-3-carboxylic acid;AKOS000263471;AS-5028;CCG-321645;CS-W007575;AC-22739;SY010127;5-METHYLISOXASOLE-3-CARBOXYLIC ACID;A6015;AM20090521;BB 0237313;FT-0620625;M2405;EN300-16526;J-019440;J-517816;Q27449789;F1984-0188

Chemical Property of 5-Methylisoxazole-3-carboxylic acid

Chemical Property:

• Appearance/Colour: slight yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 168 °C
• Refractive Index: 1.514
• Boiling Point: 312.475 °C at 760 mmHg
• PKA: 3.46±0.10(Predicted)
• Flash Point: 142.8 °C
• PSA: 63.33000
• Density: 1.348 g/cm³
• LogP: 0.68120
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 127.026943022
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

5-Methylisoxazole-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=NO1)C(=O)O
• Uses: 5-Methylisoxazole-3-carboxylic Acid is a metabolite of UTL-5b, a structural analog of the anti-arthritic drug, Leflunomide (L322750). Reactant for:Click/aza-Michael or Click/oligomeric alkyl carbodiimide esterification reactionsPreparation of aminopyrazole amide derivatives as Raf kinase inhibitors in melanoma cellsPreparation of trifluoromethoxyphenyl(thiazolyl)pyrroles and other heterocycle-bearing polyfunctionalized pyrroles via chain heterocyclization Reactant for:? ;Click/aza-Michael or Click/oligomeric alkyl carbodiimide esterification reactions1? ;Preparation of aminopyrazole amide derivatives as Raf kinase inhibitors in melanoma cells2? ;Preparation of trifluoromethoxyphenyl(thiazolyl)pyrroles and other heterocycle-bearing polyfunctionalized pyrroles via chain heterocyclization3

Technology Process of 5-Methylisoxazole-3-carboxylic acid

There total 14 articles about 5-Methylisoxazole-3-carboxylic acid 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: 79.0%

ethyl 2,4-diketopentanoate (615-79-2) → 5-methylisoxazole 3-carboxylic acid (3405-77-4)

Guidance literature:

ethyl 2,4-diketopentanoate; With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 4h; Reflux;

With sodium hydroxide; In ethanol; at 20 ℃;

With hydrogenchloride; In water;

DOI:10.1016/j.ejmech.2012.02.003

Reference yield: 45.0%

2,5-hexanedione (110-13-4) → 5-methylisoxazole 3-carboxylic acid (3405-77-4)

Guidance literature:

2,5-hexanedione; With dodecatungstosilic acid; sulfuric acid; sodium nitrite; In water; at 5 - 40 ℃;

With nitric acid; at 75 - 102 ℃; for 20.5h;

DOI:10.1002/jhet.163

Reference yield: 17.0%

3,5-dimethyl-1,2-oxazole (300-87-8) → 5-methylisoxazole 3-carboxylic acid (3405-77-4)

Guidance literature:

With chromium(VI) oxide; acetic acid; at 45 ℃; for 2h;

DOI:10.1016/S0014-827X(98)00057-3

upstream raw materials:

(5-methyl-isoxazol-3-yl)-methanol

3-acetyl-5-methylisoxazole

5-methyl-isoxazole-3-carboxylic acid methylamide

2,4-dioxo-pentanoic acid

Downstream raw materials:

α-acetyl-p-dimethylaminocinnamonitrile

5-Methyl-isoxazole-3-carboxylic acid {2-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenyl]-ethyl}-amide

5-methyl-3-isoxazolyl chloride

5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid

Refernces

• 1、 Cascioferro, Stella,Maggio, Benedetta,Raffa, Demetrio,Raimondi, Maria Valeria,Cusimano, Maria Grazia,Schillaci, Domenico,Manachini, Barbara,Leonchiks, Ainars,Daidone, Giuseppe. "A new class of phenylhydrazinylidene derivatives as inhibitors of Staphylococcus aureus biofilm formation". . p. 870 - 878. Retrieved 2016/04/20.
• 2、 Van Arnum, Susan D.,Niemczykapi, Henry J.. "The Boulton-Katritzky rearrangement of isocarboxazid". experimental part. p. 909 - 913. Retrieved 2010/01/11.