4,6-Diphenylthieno[3,4-d]-1,3-dioxol-2-one 5,5-dioxide

• Catalog No.: L13513
• CAS Number: 54714-11-3
• M. F.: C17H10O5S
• M. W.: 326.3233
• Purity: 97%

SYNONYMS

• Title: 4,6-二苯基噻吩[3,4-d]-1,3-二氧-2-酮-5,5-二氧
• 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: TDO activated carbonate; Steglich's Reagent

DATABASE IDS

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

PROPERTIES

• Purity: 97%
• Melting Point: 224-230°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否

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.