{3-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl}boronic acid

• ChemBase ID: 155848
• Molecular Formular: C18H19BN2O4S
• Molecular Mass: 370.23046
• Monoisotopic Mass: 370.1158585
• SMILES: B(c1cccc(c1)NS(=O)(=O)c1cccc2c1cccc2N(C)C)(O)O
• Canonical SMILES: OB(c1cccc(c1)NS(=O)(=O)c1cccc2c1cccc2N(C)C)O
• InChI: InChI=1S/C18H19BN2O4S/c1-21(2)17-10-4-9-16-15(17)8-5-11-18(16)26(24,25)20-14-7-3-6-13(12-14)19(22)23/h3-12,20,22-23H,1-2H3
• InChIKey: TYXMKSYBCDTGDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {3-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl}boronic acid
• IUPAC Traditional name: 3-[5-(dimethylamino)naphthalene-1-sulfonamido]phenylboronic acid
• Synonyms: 3-(5-Di-methyl-amino-naphtha-lene-1-sulfonyl-amino)-benzene-boronic acid; 3-(Dansylamido)benzeneboronic acid; 3-(Dansylamino)phenylboronic acid

Database IDs

• CAS Number: 75806-94-9
• EC Number: 278-319-1
• MDL Number: MFCD00042703
• Beilstein Number: 8012268
• PubChem SID: 162249986; 24858354
• PubChem CID: 150643

CALCULATED PROPERTIES

• Acid pKa: 7.45234
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.4091074
• LogD (pH = 7.4): 3.206418
• Log P: 3.4678
• Molar Refractivity: 98.3145 cm^3
• Polarizability: 40.721336 Å^3
• Polar Surface Area: 89.87 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 337 nm; λem 490 nm (Protein adduct); λex 337 nm; λem 517 nm in methanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C18H19BN2O4S

DETAILS

Sigma Aldrich - 30423

Application
Carbohydrate ligand in cell studies1; potent boronic acid serine protease inhibitor.2