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43720

N,N′-Disuccinimidyl carbonate

Name: <I>N,N&#8242;</I>-Disuccinimidyl carbonate
Brand: SIAL

≥95.0% (NMR), for peptide synthesis

Synonym(s):

N-Succinimidyl carbonate, DSC, Di(N-succinimidyl) carbonate

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About This Item

Empirical Formula (Hill Notation):

C₉H₈N₂O₇

CAS Number:

74124-79-1

Molecular Weight:

256.17

NACRES:

NA.22

PubChem Substance ID:

329756382

UNSPSC Code:

12352005

EC Number:

277-730-3

MDL number:

MFCD00009767

Beilstein/REAXYS Number:

1499137

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Properties

Product Name

N,N′-Disuccinimidyl carbonate, purum, ≥95.0% (NMR)

grade

purum

Quality Level

200

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

functional group

imide

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).

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Warning

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Hazard Classifications

Acute Tox. 4 Oral

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T. Kokubo et al.

Journal of the American Chemical Society, 109, 606-606 (1987)

N-hydroxysuccinimide carbonates and carbamates are useful reactive reagents for coupling ligands to lysines on proteins.

M Morpurgo et al.

Journal of biochemical and biophysical methods, 38(1), 17-28 (1999-03-17)

Ligands containing amino or hydroxyl groups were converted to their corresponding activated N-hydroxysuccinimidyl carbamate and carbonate by reaction with disuccinimidyl carbonate (DSC). The latter reagents can be used for the group-specific modification of primary amines as an alternative to the

A.K. Ghosh et al.

Tetrahedron Letters, 33, 2781-2781 (1992)

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Global Trade Item Number

SKU	GTIN
49617-250MG	04061832416083
43720-25G	04061833417072
43720-5G	04061833348444