IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product NameISOXAZOLE-5-CARBOXYLIC ACIDIUPAC Name1,2-oxazole-5-carboxylic acidMolecular StructureCAS Registry Number 21169-71-1Synonyms1,2-oxazole-5-carboxylic Acid673-088-7Isoxazole-5-carboxylic acid21169-71-15-isoxazolecarboxylic acidISOXAZOLE-5-CARBOXYLICACIDMFCD00156151F2158-0308isoxazole-5-carboxylicisoxazole 5-carboxylic acidSCHEMBL112293SCHEMBL3618206SCHEMBL5188508SCHEMBL15880622DTXSID70366185MIIQJAUWHSUTIT-UHFFFAOYSA-NIsoxazole-5-carboxylic acid, 97%SMSSF-0017806BBL100210GEO-01628SBB004319STL553782AKOS001042457CS-W000637PS-5358SY018290DB-011149ST50339231EN300-06774Z56943419Molecular FormulaC4H3NO3 Molecular Weight113.07InChIInChI=1S/C4H3NO3/c6-4(7)3-1-2-5-8-3/h1-2H,(H,6,7) InChI KeyMIIQJAUWHSUTIT-UHFFFAOYSA-NSMILESC1=C(ON=C1)C(=O)O
Patent InformationPatent IDTitlePublication DateEP2567958Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals2013US2013/217702INDOLE DERIVATIVES2013WO2012/59776INDOLE DERIVATIVES2012US2005/171346Hexahydropyridazine-3-carboxylic acid derivatives, pharmaceutical compositions containing same and methods of preparation2005
Physical Data
AppearanceLight brown crystal or powder
Melting Point, °C Solvent (Melting Point) 138 - 140146145 - 146147 - 148benzene, methanol145.5 - 146.5toluene148 - 149toluene
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHzChemical shifts1Hchloroform-d1400Chemical shifts13Cchloroform-d1100Chemical shifts1HCDCl324.8580Chemical shifts13CCDCl324.8520Chemical shifts17OCD3CN39.8554.25Chemical shifts1HCDCl3, dimethylsulfoxide-d6
Route of Synthesis (ROS)
ConditionsYieldWith borane-THF In tetrahydrofuran at 0 - 20℃;Experimental ProcedureTo a solution of isoxazole-5-carboxylic acid (1.0 g, 8.8 mmol,) in THF (10 mL) was added borane-THF complex (26.4 mL,26.4 mmol) at 0 °C. The reaction was stirred at room temperature until the substrate was consumed. The reaction was quenched with ethanol (5 mL) at 0 °C. The reaction mixture was partitioned between ethyl acetate and water. The combined organic phase was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ ethyl acetate (2: 1 to give isoxazol-5-ylmethanol (670 mg, 77.0% yield) as a light yellow oil. LCMS retention time 0.329 min; LCMS MH+ 100.77%Stage #1: isoxazole-5-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.25h;Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1h;Experimental ProcedureExample 55.2-(6-Fluoro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo pyrazine-7-carboxylic acid (1 - isoxazol-5 - l-ethyl)-amideIn a round-bottomed flask, isoxazole-5-carboxylic acid (1.0 g, 8.84 mmol) was dissolved in THF (35 ml). The solution was cooled to 0°C and triethylamine (1.4 ml, 10.0 mmol) was added followed by ethyl chloroformate (0.94 ml, 9.8 mmol). A thick precipitate was formed upon the addition of the latter. The suspension was stirred at 0°C for 15 min then a solution of sodium borohydride (1.00 g, 26.5 mmol) in water (14 ml) was added portionwise via pipet. Vigorous gas evolution was observed. The reaction mixture was stirred at 0°C for 1 h then diluted with water and saturated aqueous NH4C1 and extracted with dichloromethane (3x). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue waschromato graphed over silica gel with EtOAc/hexanes (gradient 0-50% EtOAc) to afford 513 mg (59%) of isoxazol-5-yl-methanol as a colorless oil. 1H NMR (CDC13, 300 MHz): ? (ppm) 8.23 (d, J=1.9 Hz, 1H), 6.26 - 6.30 (m, 1H), 4.82 (s, 2H), 2.13 (br. s., 1H).59%
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH315 (100%): Causes skin irritation H319 (100%): Causes serious eye irritation H335 (90%): May cause respiratory irritation Precautionary Statement CodesP261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
TransportationUnder the room temperature and away from lightStorageUnder the room temperature and away from lightShelf Life2 yearsMarket Price
DruglikenessLipinski rules componentMolecular Weight113.073logP0.372HBA2HBD1Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)63.33Rotatable Bond (RotB)1Matching Veber Rules2 https://www.chemwhat.com/isoxazole-5-carboxylic-acid-cas-21169-71-1/
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