6,7-dihydroxy-4-methyl-2H-chromen-2-one

• ChemBase ID: 59807
• Molecular Formular: C10H8O4
• Molecular Mass: 192.16812
• Monoisotopic Mass: 192.04225874
• SMILES: c12c(c(cc(=O)o1)C)cc(c(c2)O)O
• Canonical SMILES: O=c1cc(C)c2c(o1)cc(c(c2)O)O
• InChI: InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3
• InChIKey: KVOJTUXGYQVLAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dihydroxy-4-methyl-2H-chromen-2-one
• IUPAC Traditional name: 6,7-dihydroxy-4-methylcoumarin
• Synonyms: 6,7-Dihydroxy-4-methylcoumarin; 6,7-Dihydroxy-4-methyl-2H-chromen-2-one; 4-Methylesculetin; 6,7-DIHYDROXY-4-METHYLCOUMARIN; 4-METHYLESCULETIN; 6,7-二羟基-4-甲基香豆素

Database IDs

• CAS Number: 529-84-0
• EC Number: 208-470-0
• MDL Number: MFCD00006859
• Beilstein Number: 162550
• PubChem SID: 24863489; 162064570; 24847302
• PubChem CID: 5319502

CALCULATED PROPERTIES

• Acid pKa: 7.879867
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4738292
• LogD (pH = 7.4): 1.3523794
• Log P: 1.4756236
• Molar Refractivity: 49.7924 cm^3
• Polarizability: 18.78947 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble
• Melting Point: 274-276 °C(lit.); ca 275°C dec.
• Absorption Wavelength: λmax 348 nm
• Fluorescence: λex 360 nm; λem 459 nm in 0.1 M Tris pH 9.0

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: IRRITANT
• RTECS: GN6384500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• 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: ≥98.0% (TLC); 97%; 98%
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C10H8O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02157746

(4-Methylesculetin)

MP Biomedicals - 05213720

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 119903

Application
Can be used as a fluorescent sensor to monitor the consumption of a boronic acid in a Suzuki cross-coupling reaction. Fluorescence is easily detectable to the naked eye using a standard hand-held long-wave UV lamp (365 nm)1.

Sigma Aldrich - 37705

Application
suitable as pH-indicator