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Sigma-Aldrich

N,N′-Disuccinimidyl carbonate

≥95%, for peptide synthesis

Synonym(s):

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

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1 G
$41.99
5 G
$108.30
25 G
$381.00

About This Item

Empirical Formula (Hill Notation):
C9H8N2O7
CAS Number:
Molecular Weight:
256.17
Beilstein/REAXYS Number:
1499137
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

$41.99

List Price$44.20Save 5%

In StockDetails


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Product Name

N,N′-Disuccinimidyl carbonate, ≥95%

Quality Level

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

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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General description

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

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.[1]
  • As an alkoxycarbonylating reagent for a variety of primary and sterically hindered secondary alcohols, which further allows the synthesis of different structurally diverse carbamates.[2]
  • As a coupling agent for the synthesis of thiophospholipids, commonly used for anchoring biomembranes to gold surfaces.[3]
It can also be used to prepare a heterobifunctional, cleavable linker-SVEC-(succinimide vinylsufonylethyl carbonate)-for thiol modified-DNA.

pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

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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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)
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 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)
Tetrahedron Letters, 33, 2781-2781 (1992)

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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