4-hydroxy-2,5-diphenyl-2,3-dihydro-1λ6-thiophene-1,1,3-trione

• ChemBase ID: 138628
• Molecular Formular: C16H12O4S
• Molecular Mass: 300.32908
• Monoisotopic Mass: 300.04562986
• SMILES: c1ccc(cc1)C1C(=O)C(=C(S1(=O)=O)c1ccccc1)O
• Canonical SMILES: O=C1C(=C(S(=O)(=O)C1c1ccccc1)c1ccccc1)O
• InChI: InChI=1S/C16H12O4S/c17-13-14(18)16(12-9-5-2-6-10-12)21(19,20)15(13)11-7-3-1-4-8-11/h1-10,15,18H
• InChIKey: UIVWXNPUCAHAJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2,5-diphenyl-2,3-dihydro-1λ^6-thiophene-1,1,3-trione
• IUPAC Traditional name: 4-hydroxy-2,5-diphenyl-2H-1λ^6-thiophene-1,1,3-trione
• Synonyms: HOTDO; 2,5-Diphenyl-4-hydroxy-3-thiophenone 1,1-dioxide; 4-Hydroxy-2,5-diphenyl-3-thiophenone 1,1-dioxide; 4-Hydroxy-2,5-diphenyl-3(2H)-thiophenone 1,1-dioxide; 4-Hydroxy-2,5-diphenyl-3-thiophenone 1,1-dioxide; 2,5-Diphenyl-4-hydroxy-3-oxo-2,3-dihydrothiophene 1,1-dioxide; 4-Hydroxy-3-oxo-2,5-diphenyl-2,3-dihydrothiophene 1,1-dioxide; 2,5-二苯基-3-氧代-4-羟基-2,3-二氢噻吩-1,1-二氧化物; 4-羟基-2,5-二苯基-3-噻吩酮 1,1-二氧化物; 2,5-二苯基-3-氧代-4-羟基-2,3-二氢噻吩-1,1-二氧化物; 2,5-二苯基-4-羟基-3-氧-2,3-二氢噻吩 1,1-二氧化物

Database IDs

• CAS Number: 54714-10-2
• MDL Number: MFCD00075268
• Beilstein Number: 544870
• PubChem SID: 24861176; 162232880
• PubChem CID: 388546

CALCULATED PROPERTIES

• Acid pKa: 6.248654
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3604445
• LogD (pH = 7.4): 1.2525302
• Log P: 2.4317071
• Molar Refractivity: 80.0432 cm^3
• Polarizability: 31.24351 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 238-240 °C(lit.); 238-241°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (S); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C16H12O4S

DETAILS

Sigma Aldrich - 43082

Other Notes
Starting material for preparing very reactive reagents to activate carboxylic acids1,2

REFERENCES

• Can be used in preparation of self-indicating active esters for linking amino acid residues to solid phase support: Angew. Chem. Int. Ed ., 15, 444 (1976). Compare 4,6-Diphenylthieno[3,4-d]-1,3-dioxol-2-one 5,5-dioxide, L13513. For peptide reagents, see Appendix 6.