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43720

Sigma-Aldrich

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:
Molecular Weight:
256.17
Beilstein:
1499137
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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).

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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More Documents

Quotes and Ordering

Articles

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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