43720

N,N′-Disuccinimidyl carbonate

purum, ≥95.0% (NMR)

• Synonym(s): Di(N-succinimidyl) carbonate, N-Succinimidyl carbonate, DSC
• Empirical Formula (Hill Notation): C₉H₈N₂O₇
• CAS Number: 74124-79-1
• Molecular Weight: 256.17
• Beilstein: 1499137
• EC Number: 277-730-3
• MDL number: MFCD00009767
• PubChem Substance ID: 329756382
• NACRES: NA.22

Properties

• Quality Level: 200
• grade: purum
• assay: ≥95.0% (NMR)
• form: powder
• reaction suitability: reaction type: Carbonylations
• impurities: ~3% N-hydroxysuccinimide (NMR)
• mp: 190 °C (dec.) (lit.)
• application(s): peptide synthesis
• storage temp.: −20°C
• SMILES string: O=C1CCC(=O)N1OC(=O)ON2C(=O)CCC2=O
• 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
• InChI key: PFYXSUNOLOJMDX-UHFFFAOYSA-N

Description

Application

N,N′-Disuccinimidyl carbonate (DSC) can be used to synthesize:

• Various carbamate derivatives from primary and sterically hindered secondary alcohols by alkoxycarbonylation.
• Active carbonate resins from 4-hydroxymethylpolystyrene and 4-hydroxymethyl-3-nitrobenzamido resins via hydroxy functional groups.
• Aza-glycinyl dipeptides, important intermediates for the preparation of various azapeptides.

It may be also used:

• In the two-step preparation of 5-(6-(azidomethyl)nicotinamido)pentanoic acid, a copper-chelating picolyl azide derivative.
• To activate the hydroxyl group of the hapten, γ-hydroxyphenylbutazone (HPBZ) so that HPBZ can effectively bind with human serum albumin(HSA)-immunogen to form a hapten-protein conjugate.

Other Notes

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

Safety Information

• Pictograms: GHS07,GHS08
• Signal Word: Warning
• Hazard Statements: H302 - H319 - H373
• Precautionary Statements: P260 - P264 - P270 - P301 + P312 - P305 + P351 + P338 - P314
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves