sodium 2-[(4-azido-2-nitrophenyl)amino]ethane-1-sulfonate

• ChemBase ID: 161037
• Molecular Formular: C8H8N5NaO5S
• Molecular Mass: 309.23439
• Monoisotopic Mass: 309.01438366
• SMILES: c1(NCCS(=O)(=O)[O-])c(cc(cc1)N=[N+]=[N-])[N+](=O)[O-].[Na+]
• Canonical SMILES: [N-]=[N+]=Nc1ccc(c(c1)[N+](=O)[O-])NCCS(=O)(=O)[O-].[Na+]
• InChI: InChI=1S/C8H9N5O5S.Na/c9-12-11-6-1-2-7(8(5-6)13(14)15)10-3-4-19(16,17)18;/h1-2,5,10H,3-4H2,(H,16,17,18);/q;+1/p-1
• InChIKey: GEOYUPVCDYHHSZ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[(4-azido-2-nitrophenyl)amino]ethane-1-sulfonate
• IUPAC Traditional name: sodium 2-[(4-azido-2-nitrophenyl)amino]ethanesulfonate
• Synonyms: 2-[(4-Azido-2-nitrophenyl)amino]ethanesulfonic Acid Monosodium Salt Dihydrate; NAP-TAURINE; N-(4-Azido-2-nitrophenyl)-2-aminoethylsulfonate, Sodium Salt, Dihydrate

Database IDs

• CAS Number: 352000-05-6
• PubChem SID: 162255172
• PubChem CID: 6093663

CALCULATED PROPERTIES

• Acid pKa: -1.8097302
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.0137709
• LogD (pH = 7.4): -1.013776
• Log P: -0.34956357
• Molar Refractivity: 67.4287 cm^3
• Polarizability: 24.09987 Å^3
• Polar Surface Area: 144.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Water
• Apperance: Brick-Red Powder
• Melting Point: >135°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - A856000

Photolysis of NAP-taurine produces a highly reactive nitrene which acts as a general covalent labeling reagent.

REFERENCES

• Staros, J.V. and Richards, F.M.: Biochemistry, 13, 13, 2720 (1974)