5-methyl-1,2-oxazole-3-carboxylic acid

• ChemBase ID: 24661
• Molecular Formular: C5H5NO3
• Molecular Mass: 127.0981
• Monoisotopic Mass: 127.02694303
• SMILES: c1(noc(c1)C)C(=O)O
• Canonical SMILES: Cc1cc(no1)C(=O)O
• InChI: InChI=1S/C5H5NO3/c1-3-2-4(5(7)8)6-9-3/h2H,1H3,(H,7,8)
• InChIKey: BNMPIJWVMVNSRD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-1,2-oxazole-3-carboxylic acid
• IUPAC Traditional name: 5-methyl-1,2-oxazole-3-carboxylic acid
• Synonyms: 3-Carboxy-5-methylisoxazole; 5-Methyl-3-isoxazolecarboxylic acid; 5-Methylisoxazole-3-carboxylic acid; 5-Methylisoxazole-3-carboxylic acid; 5-甲基异噁唑-3-甲酸

Database IDs

• CAS Number: 3405-77-4
• EC Number: 222-289-4
• MDL Number: MFCD01318162
• Beilstein Number: 114094
• PubChem SID: 160987968; 24883349
• PubChem CID: 76947

CALCULATED PROPERTIES

• Acid pKa: 3.915788
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.0096961
• LogD (pH = 7.4): -2.6245775
• Log P: 0.58078575
• Molar Refractivity: 29.5339 cm^3
• Polarizability: 10.600624 Å^3
• Polar Surface Area: 63.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 106-110 °C(lit.); 171°C; 171-173°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C5H5NO3

DETAILS

Sigma Aldrich - 644676

Packaging
1, 5 g in glass bottle
Application
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