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N,N′-Disuccinimidyl carbonate

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

≥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

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Properties

Product Name

N,N′-Disuccinimidyl carbonate, ≥95%

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

Description

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.
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.

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 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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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)

Multi-subject atlas-based auto-segmentation reduces interobserver variation and improves dosimetric parameter consistency for organs at risk in nasopharyngeal carcinoma: A multi-institution clinical study.

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)

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