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N,N′-Disuccinimidyl carbonate

SIAL/43720 - purum, ≥95.0% (NMR)

Synonym: N-Succinimidyl carbonate; DSC; Di(N-succinimidyl) carbonate

CAS Number: 74124-79-1
Empirical Formula (Hill Notation): C9H8N2O7
Molecular Weight: 256.17
EC Number: 277-730-3
MDL Number: MFCD00009767
Linear Formula: C9H8N2O7
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-43720-5G 5 g
 $142.00
1/EA		 Add To Favorites
45-43720-25G 25 g
 $422.00
1/EA		 Add To Favorites

 

application(s) peptide synthesis
assay ≥95.0% (NMR)
form powder
functional group imide
grade purum
impurities ~3% N-hydroxysuccinimide (NMR)
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
mp 190 °C (dec.) (lit.)
Quality Level 200 
reaction suitability reaction type: Carbonylations
SMILES string O=C1CCC(=O)N1OC(=O)ON2C(=O)CCC2=O
storage temp. −20°C
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).
Purity ≥95.0% (NMR)
mp 190 °C (dec.) (lit.)
Storage Temp. −20°C
UNSPSC 12352005

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