2,5-dioxopyrrolidin-1-yl 2-[2-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)ethanesulfonyl]ethyl carbonate

• ChemBase ID: 153742
• Molecular Formular: C14H16N2O12S
• Molecular Mass: 436.34804
• Monoisotopic Mass: 436.04239496
• SMILES: C1CC(=O)N(C1=O)OC(=O)OCCS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCCS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C14H16N2O12S/c17-9-1-2-10(18)15(9)27-13(21)25-5-7-29(23,24)8-6-26-14(22)28-16-11(19)3-4-12(16)20/h1-8H2
• InChIKey: XUDGDVPXDYGCTG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 2-[2-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)ethanesulfonyl]ethyl carbonate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 2-[2-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)ethanesulfonyl]ethyl carbonate
• Synonyms: BSOCOES; Bis[2-(N-succinimidyl-oxycarbonyloxy)ethyl] sulfone; 1,1'-[Sulfonylbis(2,1-ethanediyloxycarbonyloxy)]bis-2,5-pyrrolidinedione; NSC 338309; Bis[2-(succinimidooxycarbonyloxy)ethyl] Sulfone

Database IDs

• CAS Number: 57683-72-4
• EC Number: 260-904-8
• MDL Number: MFCD00047123
• Beilstein Number: 1521053
• PubChem SID: 162247881; 24886547
• PubChem CID: 93771

CALCULATED PROPERTIES

• Acid pKa: 17.333178
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): -1.8085816
• LogD (pH = 7.4): -1.8085816
• Log P: -1.8085816
• Molar Refractivity: 85.244 cm^3
• Polarizability: 35.478443 Å^3
• Polar Surface Area: 179.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: White Solid
• Melting Point: 168-170°C; 169-173 °C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (CHN)
• Empirical Formula (Hill Notation): C14H16N2O12S

DETAILS

Sigma Aldrich - 73361

Other Notes
Homobifunctional crosslinking reagent for proteins1,2,3; cross-linking reagents used as molecular rulers4

Toronto Research Chemicals - B585000

An amine reactive homobifunctional crosslinking reagent. Used to crosslink β-endorphin to opioid receptors.Spacer Arm: 13.0 Angstroms

REFERENCES

• Zarling, D.A., et al.: J. Immunol., 124, 913 (1980)
• Howard, A.D., et al.: J. Biol. Chem., 260, 10833 (1980)
• Bouizar, Z., et al.: Eur. J. Biochem., 155, 141 (1986)