diphenyl-2H-5λ6-thieno[3,4-d][1,3]dioxole-2,5,5-trione

• ChemBase ID: 302349
• Molecular Formular: C17H10O5S
• Molecular Mass: 326.3233
• Monoisotopic Mass: 326.02489442
• SMILES: c1ccc(cc1)C1=c2c(=C(S1(=O)=O)c1ccccc1)oc(=O)o2
• Canonical SMILES: O=c1oc2=C(c3ccccc3)S(=O)(=O)C(=c2o1)c1ccccc1
• InChI: InChI=1S/C17H10O5S/c18-17-21-13-14(22-17)16(12-9-5-2-6-10-12)23(19,20)15(13)11-7-3-1-4-8-11/h1-10H
• InChIKey: UEOYFCIGZWQXTP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl-2H-5λ^6-thieno[3,4-d][1,3]dioxole-2,5,5-trione
• IUPAC Traditional name: diphenyl-5λ^6-thieno[3,4-d][1,3]dioxole-2,5,5-trione
• Synonyms: Steglich's Reagent; TDO activated carbonate; 4,6-Diphenylthieno[3,4-d]-1,3-dioxol-2-one 5,5-dioxide; 4,6-二苯基噻吩[3,4-d]-1,3-二氧-2-酮-5,5-二氧

Database IDs

• CAS Number: 54714-11-3
• EC Number: 259-301-2
• MDL Number: MFCD00040564
• Beilstein Number: 1396884

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.6422966
• LogD (pH = 7.4): 2.6422966
• Log P: 2.6422966
• Molar Refractivity: 85.4268 cm^3
• Polarizability: 32.958214 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 224-230°C

Safety Information

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

Product Information

• Purity: 97%

REFERENCES

• Reagent for the formation of active esters for peptide coupling or esterification. In the presence of 1 equiv. of base, these enolize with formation of a deep red anion in which the enolate oxygen is well placed to facilitate aminolysis or alcoholysis: Angew. Chem. Int. Ed., 15, 444 (1976). Aminolysis occurs more rapidly in dichloromethane than in the more polar DMF. Progress of acylation can readily be followed by disappearance of the red color of the active ester, giving scope for the possibility of automatic monitoring of the reaction: J. Chem. Soc., Chem. Commun., 1870 (1987).
• Reacts with t-butanol and pyridine to give an activated reagent for the formation of Boc derivatives of amino acids which can then further react with the reagent to form active esters for peptide coupling: Angew. Chem. Int. Ed., 18, 307 (1979); Liebigs Ann. Chem., 437 (1988). For peptide reagents, see Appendix 6.