3-methylfuran-2-carboxylic acid

• ChemBase ID: 76116
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: o1ccc(c1C(=O)O)C
• Canonical SMILES: OC(=O)c1occc1C
• InChI: InChI=1S/C6H6O3/c1-4-2-3-9-5(4)6(7)8/h2-3H,1H3,(H,7,8)
• InChIKey: BNYIQEFWGSXIKQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylfuran-2-carboxylic acid
• IUPAC Traditional name: 3-methylfuran-2-carboxylic acid
• Synonyms: 3-Methylfuran-2-carboxylic acid; 3-Methyl-2-furoic acid; 3-Methyl-2-furoic acid; 3-Methyl-2-furancarboxylic acid 3-Methyl-2-furanoic acid; 3-甲基呋喃-2-羧酸; 3-甲基-2-糠酸

Database IDs

• CAS Number: 4412-96-8
• EC Number: 224-571-2
• MDL Number: MFCD00014111
• Beilstein Number: 116183
• PubChem SID: 162041031; 24884952
• PubChem CID: 78127

CALCULATED PROPERTIES

• Acid pKa: 2.9569783
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.2971299
• LogD (pH = 7.4): -2.2749848
• Log P: 1.2044967
• Molar Refractivity: 30.7463 cm^3
• Polarizability: 11.386855 Å^3
• Polar Surface Area: 50.44 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129 - 131°C; 133-137°C; 134-138 °C; 136-137°C
• Hydrophobicity(logP): 1.26

Safety Information

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

Product Information

• Purity: 95%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C6H6O3

DETAILS

Sigma Aldrich - 667994

Application
Used in a palladium-catalyzed cross-coupling between heteroaryl carboxylic acids and aryl bromides leading to arylated heterocycles.1 Also used in a palladium-catalyzed asymmetric hydrogenation.2
Packaging
1, 5 g in glass bottle