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Merck

43720

N,N′-Disuccinimidyl carbonate

≥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

Product Name

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

InChI key

PFYXSUNOLOJMDX-UHFFFAOYSA-N

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

SMILES string

O=C1CCC(=O)N1OC(=O)ON2C(=O)CCC2=O

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

functional group

imide

storage temp.

−20°C

Quality Level

200

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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).

signalword

Warning

pictograms

Health hazardExclamation mark
GHS08,GHS07

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2 Oral

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1921
BCCB6748
BCBW0349
BCBT6035
BCBS5912V

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Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides
Alsina J, et al.
Tetrahedron Letters, 38(5), 883-886 (1997)
A.K. Ghosh et al.
Tetrahedron Letters, 33, 2781-2781 (1992)
N. Nimura et al.
Analytical Chemistry, 58, 2372-2372 (1986)
Arun K Ghosh et al.
Tetrahedron letters, 33(20), 2781-2784 (1992-05-12)
An efficient and mild method for alkoxycarbonylation of amines is described, utilizing commercially available N,N'-disuccinimidyl carbonate.
T. Kokubo et al.
Journal of the American Chemical Society, 109, 606-606 (1987)
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