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Merck
CN

225827

N,N′-Disuccinimidyl carbonate

≥95%, 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:
24853526
UNSPSC Code:
12352108
EC Number:
277-730-3
MDL number:
MFCD00009767
Beilstein/REAXYS Number:
1499137

Key Documents

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Product Name

N,N′-Disuccinimidyl carbonate, ≥95%

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

assay

≥95%

form

powder or crystals

reaction suitability

reaction type: Carbonylations

mp

190 °C (dec.) (lit.)

application(s)

peptide synthesis

functional group

imide

storage temp.

2-8°C

Quality Level

200

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Application

N,N′-Disuccinimidyl carbonate may be used:
  • As an activating reagent for the reactive patterning of polymer brushes to couple primary amines via post-functionalization.
  • As an alkoxycarbonylating reagent for a variety of primary and sterically hindered secondary alcohols, which further allows the synthesis of different structurally diverse carbamates.
  • As a coupling agent for the synthesis of thiophospholipids, commonly used for anchoring biomembranes to gold surfaces.
It can also be used to prepare a heterobifunctional, cleavable linker-SVEC-(succinimide vinylsufonylethyl carbonate)-for thiol modified-DNA.

General description

N,N′-Disuccinimidyl carbonate is used for the HPLC determination of amino compounds.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

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
BCBS4774V

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Tetrahedron Letters, 33, 2781-2781 (1992)
N,N?-Disuccinimidyl carbonate as a coupling agent in the synthesis of thiophospholipids used for anchoring biomembranes to gold surfaces
Boden N, et al.
Tetrahedron, 54(38), 11537-11548 (1998)
Chang-Juan Tao et al.
Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology, 115(3), 407-411 (2015-05-31)
To assess whether consensus guideline-based atlas-based auto-segmentation (ABAS) reduces interobserver variation and improves dosimetric parameter consistency for organs at risk (OARs) in nasopharyngeal carcinoma (NPC). Eight radiation oncologists from 8 institutes contoured 20 OARs on planning CT images of 16
N, N?-Disuccinimidyl Carbonate: A Useful Reagent for Alkoxycarbonylation of Amines
Ghosh KA, et al.
Tetrahedron Letters, 33(20), 2781-2781 (1992)
Reactive patterning via post-functionalization of polymer brushes utilizing disuccinimidyl carbonate activation to couple primary amines
Diamanti S, et al.
Polymer, 49(17), 3770-3779 (2008)
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