bis(2,5-dioxopyrrolidin-1-yl) carbonate

• ChemBase ID: 88140
• Molecular Formular: C9H8N2O7
• Molecular Mass: 256.16902
• Monoisotopic Mass: 256.03315061
• SMILES: N1(OC(=O)ON2C(=O)CCC2=O)C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2
• InChIKey: PFYXSUNOLOJMDX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2,5-dioxopyrrolidin-1-yl) carbonate
• IUPAC Traditional name: bis(2,5-dioxopyrrolidin-1-yl) carbonate
• Synonyms: N-Succinimidyl carbonate; Di(N-succinimidyl) carbonate; N,N′-Disuccinimidyl carbonate; Su2O; N,N'-Disuccinimidyl carbonate; N,N'-Disuccinimidyl carbonate; DSC; 1,1'-[Carbonylbis(oxy)]dipyrrolidine-2,5-dione; Bis(2,5-dioxopyrrolidin-1-yl) carbonate; N-琥珀酰氨基碳酸酯; 二(N-琥珀酰亚胺基)碳酸酯; N,N′-二琥珀酰亚胺基碳酸酯; N,N'-二琥珀酰亚胺基碳酸酯

Database IDs

• CAS Number: 74124-79-1
• EC Number: 277-730-3
• MDL Number: MFCD00009767
• Beilstein Number: 1499137
• PubChem SID: 24853526; 162075172; 24867355
• PubChem CID: 676246

CALCULATED PROPERTIES

• Acid pKa: 17.328205
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -1.0107778
• LogD (pH = 7.4): -1.0107778
• Log P: -1.0107778
• Molar Refractivity: 50.6058 cm^3
• Polarizability: 20.371552 Å^3
• Polar Surface Area: 110.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 190 °C (dec.)(lit.); 190(dec.)°C; 190°C dec.

Safety Information

• Storage Warning: Harmful/Irritant/Moisture Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95%; ≥95.0% (NMR); 95+%; 98%; tech. 85%, remainder N-Hydroxysuccinimide
• Grade: purum
• Impurities: ~3% N-hydroxysuccinimide (NMR)
• Empirical Formula (Hill Notation): C9H8N2O7

DETAILS

Sigma Aldrich - 225827

Application
Used to prepare a heterobifucntional, cleavable linker-SVEC-(succinimide vinylsufonylethyl carbonate)-for thiol modified-DNA.1
Useful reagent for the synthesis of carbamates.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 43720

Other Notes
Convenient reagent for preparing N-succinimidyl esters of N-protected amino acids and other acids;1 activated carbonate, e.g. synthesis of ureas and carbamates;2,3 coupling of ligands to proteins (via lysines).4