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Sigma-Aldrich

N,N′-Disuccinimidyl carbonate

≥95%

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Synonym(s):
N-Succinimidyl carbonate, DSC, Di(N-succinimidyl) carbonate
Empirical Formula (Hill Notation):
C9H8N2O7
CAS Number:
Molecular Weight:
256.17
Beilstein:
1499137
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95%

form

powder or crystals

reaction suitability

reaction type: Carbonylations

mp

190 °C (dec.) (lit.)

application(s)

peptide synthesis

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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This Item
4372046920P1162
form

powder or crystals

form

powder

form

powder

form

powder

mp

190 °C (dec.) (lit.)

mp

190 °C (dec.) (lit.)

mp

150-153 °C (lit.)

mp

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

reaction type: Carbonylations

reaction suitability

reaction type: Carbonylations

reaction suitability

-

reaction suitability

-

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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Journal of the Chemical Society. Chemical Communications, 1308-1308 (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)
N, N?-Disuccinimidyl Carbonate: A Useful Reagent for Alkoxycarbonylation of Amines
Ghosh KA, et al.
Tetrahedron Letters, 33(20), 2781-2781 (1992)
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)

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