NorrChemica™
N,N′-Disuccinimidyl carbonate (DSC) | CAS 74124-79-1 | ≥95%
N,N′-Disuccinimidyl carbonate (DSC) | CAS 74124-79-1 | ≥95%
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Technical Specifications
| CAS Number | 74124-79-1 |
| EC / EINECS Number | 277-730-3 |
| MDL Number | MFCD00009767 |
| SMILES | C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O |
| InChI | 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 |
| InChIKey | PFYXSUNOLOJMDX-UHFFFAOYSA-N |
| PubChem CID | 676246 |
| Molecular Formula | C₉H₈N₂O₇ |
| Molecular Weight | 256.17 g/mol |
| Melting Point | 190 °C (dec.) |
| Solubility | Soluble in acetonitrile, DMSO, and most organic solvents; insoluble in water. |
| Purity | ≥95% |
| Physical Form | White to off-white crystalline powder |
| HS Code | 2925.19 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store refrigerated (2–8 °C) in a tightly sealed container, protected from moisture |
Product Description & Scientific Applications
N,N′-Disuccinimidyl carbonate — DSC, di(N-succinimidyl) carbonate — is a carbonylating and activating reagent carrying two N-hydroxysuccinimide groups on a central carbonyl. The succinimidyl groups are good leaving groups, allowing DSC to convert carboxylic acids into N-succinimidyl esters and to activate alcohols or amines as N-succinimidyl carbonates or carbamates. DSC is a white to off-white crystalline solid, soluble in acetonitrile, DMF, DMSO and other organic solvents but insoluble in water, and is moisture-sensitive.
Common Scientific Applications
- N-Succinimidyl (NHS) esters from carboxylic acids: DSC converts N-protected amino acids and other carboxylic acids into their N-succinimidyl esters for amide and peptide bond formation.
- Alcohol activation, carbamates and ureas: as an alkoxycarbonylating reagent, DSC activates primary and sterically hindered secondary alcohols as N-succinimidyl carbonates, which react with amines to give structurally diverse carbamates; it is likewise used to prepare ureas, serving as a crystalline phosgene analogue for carbonyl transfer.
- Bioconjugation and surface immobilisation: the N-succinimidyl carbonates and carbamates derived from DSC couple ligands to lysine amines on proteins, and are used to functionalise solid supports, polymer brushes and gold-anchored thiophospholipids for biomolecule attachment.
- Cleavable linkers and amino-compound analysis: DSC is used to prepare the heterobifunctional, cleavable linker SVEC (succinimidyl vinylsulfonylethyl carbonate) for thiol-modified DNA, and as a derivatising reagent for the HPLC determination of amino compounds.
Further Reading
For guidance on selecting between carbodiimides, aminium/uronium salts, phosphonium salts and other reagent classes for amide and peptide bond formation, see NorrChemica's Lab Journal guide: Choosing a Coupling Reagent for Amide and Peptide Bond Formation.
Shipping Destinations
- EU & UK: Priority delivery, 2–5 business days.
- United States (DDP): 3–7 business days, duties and taxes prepaid.
- EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
- Worldwide: 7–14 business days, selected locations.
Safety Information
| GHS Pictograms |
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| Signal Word | Warning |
| Hazard Class | Not regulated for transport |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H302 - H315 - H319 |
| P-Statements | P264 - P270 - P280 - P301+P312 - P302+P352 - P305+P351+P338 - P330 - P332+P313 - P337+P313 - P362+P364 - P501 |
