7-fluoro-4-hydroxy-2H-chromen-2-one

• ChemBase ID: 143627
• Molecular Formular: C9H5FO3
• Molecular Mass: 180.1326032
• Monoisotopic Mass: 180.02227224
• SMILES: c1cc2c(cc(=O)oc2cc1F)O
• Canonical SMILES: Fc1ccc2c(c1)oc(=O)cc2O
• InChI: InChI=1S/C9H5FO3/c10-5-1-2-6-7(11)4-9(12)13-8(6)3-5/h1-4,11H
• InChIKey: FSWKHPJLMMGTBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-fluoro-4-hydroxy-2H-chromen-2-one
• IUPAC Traditional name: 7-fluoro-4-hydroxychromen-2-one
• Synonyms: 7-Fluoro-4-hydroxy-1(2H)-benzopyran-2-one; 7-Fluoro-4-hydroxy-2H-chromen-2-one; 7-Fluoro-4-hydroxycoumarin

Database IDs

• CAS Number: 2145-27-9
• MDL Number: MFCD11845381
• PubChem SID: 162237845
• PubChem CID: 54694570

CALCULATED PROPERTIES

• Acid pKa: 5.6051807
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.92140305
• LogD (pH = 7.4): -0.5908606
• Log P: 1.1725147
• Molar Refractivity: 43.6573 cm^3
• Polarizability: 16.078648 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 220-225 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Empirical Formula (Hill Notation): C9H5FO3

DETAILS

Sigma Aldrich - 732982

Packaging
250 mg in glass bottle
Application
Reactant for:
• Enantioselective synthesis of polycyclic coumarins via in situ formed primary amine-imine-catalyzed asymmetric Michael addition to cyclic enones1
• Preparation of dicoumarol analogs as inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1) as agents active against human pancreatic and colon cancer cells2
• Imidazolidinecarboxylic acid-catalyzed asymmetric Michael reaction with unsaturated ketones in a highly atom-economic catalytic one-step formation of optically active warfarin anticoagulant3
• Asymmetric synthesis of functionalized α-keto esters and their hemiketal and hemiaminal derivatives via direct Michael addition with unsaturated α-keto esters catalyzed by bisoxazoline-copper(II) complexes4