3-[4-(bromomethyl)phenyl]-7-(diethylamino)-2H-chromen-2-one

• ChemBase ID: 154231
• Molecular Formular: C20H20BrNO2
• Molecular Mass: 386.2823
• Monoisotopic Mass: 385.06774089
• SMILES: CCN(CC)c1ccc2cc(c(=O)oc2c1)c1ccc(cc1)CBr
• Canonical SMILES: CCN(c1ccc2c(c1)oc(=O)c(c2)c1ccc(cc1)CBr)CC
• InChI: InChI=1S/C20H20BrNO2/c1-3-22(4-2)17-10-9-16-11-18(20(23)24-19(16)12-17)15-7-5-14(13-21)6-8-15/h5-12H,3-4,13H2,1-2H3
• InChIKey: WTCCANMBFQWZMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[4-(bromomethyl)phenyl]-7-(diethylamino)-2H-chromen-2-one
• IUPAC Traditional name: 3-[4-(bromomethyl)phenyl]-7-(diethylamino)chromen-2-one
• Synonyms: 3-(4-(Bromomethyl)phenyl)-7-(diethylamino)-2H-1-benzopyran-2-one; MPAC-Br; 3-[4-(Bromomethyl)phenyl]-7-(diethylamino)coumarin

Database IDs

• CAS Number: 177093-58-2
• MDL Number: MFCD07784444
• PubChem SID: 24848784; 162248370
• PubChem CID: 10738888

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.0218177
• LogD (pH = 7.4): 5.0455337
• Log P: 5.0458446
• Molar Refractivity: 102.7769 cm^3
• Polarizability: 38.2878 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 150-155 °C
• Fluorescence: λex 402 nm; λem 476 nm in ethanol

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-H413
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (N)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C20H20BrNO2

DETAILS

Sigma Aldrich - 14653

Other Notes
HPLC-precolumn-derivatization reagent for carboxylic acids; improved "version" of the classical BMC (Fluka 17623), because it emits at longer wavelength and has stronger fluorescence. e.g. LOD of lauric acid: 17 fmol in 10 microliter1