disodium 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodo-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)

• ChemBase ID: 295434
• Molecular Formular: C20H2Cl4I4Na2O5
• Molecular Mass: 1017.6363
• Monoisotopic Mass: 1015.46306445
• SMILES: c1c2c(c(c(c1I)[O-])I)Oc1c(cc(c(c1I)[O-])I)C12c2c(c(c(c(c2Cl)Cl)Cl)Cl)C(=O)O1.[Na+].[Na+]
• Canonical SMILES: [O-]c1c(I)cc2c(c1I)Oc1c(C32OC(=O)c2c3c(Cl)c(Cl)c(c2Cl)Cl)cc(c(c1I)[O-])I.[Na+].[Na+]
• InChI: InChI=1S/C20H4Cl4I4O5.2Na/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28;;/h1-2,29-30H;;/q;2*+1/p-2
• InChIKey: KCQREHTWEUECQT-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodo-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)
• IUPAC Traditional name: disodium 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)
• Synonyms: Acid Red 94; C.I. 45440; Rose Bengal; 孟加拉玫瑰红

Database IDs

• CAS Number: 632-69-9
• EC Number: 211-183-3
• MDL Number: MFCD00151169
• Beilstein Number: 3645857
• Merck Index: 148262
• PubChem SID: 180680965
• PubChem CID: 69438

CALCULATED PROPERTIES

• Acid pKa: 6.4986353
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 9.970146
• LogD (pH = 7.4): 8.645218
• Log P: 10.0123
• Molar Refractivity: 184.9899 cm^3
• Polarizability: 63.55118 Å^3
• Polar Surface Area: 81.65 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300°C

Safety Information

• Storage Warning: Light Sensitive
• RTECS: LM5920000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

REFERENCES

• Photosensitizer, widely used for the generation of singlet oxygen. For use of this species in the ene reaction with alkenes to give allylic hydroperoxides, readily reducible to allylic alcohols, see. e.g.: J. Org. Chem., 28, 3217 (1963).
• See also: Singlet dioxygen: Active Oxygen in Chemistry, C. S. Foote, Ed., Blackie A. & P., Glasgow (1995), p. 105; Reactions of singlet oxygen with alkenes: Org. React., 20, 133 (1973); Chem. Rev., 71, 395 (1971); 79, 359 (1979); Tetrahedron, 37, 1825 (1981); Singlet Oxygen, H. H. Wasserman and R. W. Murray, Eds., Academic Press, N.Y. (1979).
• Can be solubilized in dichloromethane, etc. by 18-crown-6, or Aliquat. 336, extending its applicability to aprotic systems: Synthesis, 783 (1975).