Identification | More | [Name]
N,N'-Disuccinimidyl carbonate | [CAS]
74124-79-1 | [Synonyms]
2,5-PYRROLIDINEDIONE, 1,1'-[CARBONYLBIS(OXY)]BIS- BIS(N-SUCCINIMIDYL) CARBONATE DI-(N,N'-SUCCINIMIDYL) CARBONATE DI(N-SUCCINIMIDYL) CARBONATE DI(SUCCINIMIDO) CARBONATE DISUCCINIMIDYL CARBONATE DSC LABOTEST-BB LT00847311 N,N'-DISUCCINIMIDYL CARBONATE N-SUCCINIMIDYL CARBONATE SU2O (SUO)2CO TIMTEC-BB SBB005976 N,N'-DISUCCINIMIDYL CARBONATE, TECH. DSC [N,N'-DISUCCINIMIDYL CARBONATE] N,N'-Disuccinimidyl carbonate (DSC) N,N'-DisuccinimidylCarbonate98% N,N'-Disuccinimido Carbonate DSCsee24500 N,N'-Disuccinimidyl | [EINECS(EC#)]
277-730-3 | [Molecular Formula]
C9H10N2O7 | [MDL Number]
MFCD00009767 | [Molecular Weight]
258.18 | [MOL File]
74124-79-1.mol |
Chemical Properties | Back Directory | [Appearance]
white to slightly yellow crystalline powder | [Melting point ]
190 °C (dec.)(lit.) | [Boiling point ]
399.41°C (rough estimate) | [density ]
1.5670 (rough estimate) | [refractive index ]
1.5600 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Dichloromethane (Slightly, Heated), DMSO | [form ]
Crystalline Powder | [color ]
White to slightly yellow | [Water Solubility ]
Soluble in dimethyl sulfoxide, hot pyridine, acetonitrile and most organic solvents. Insoluble in water. | [Detection Methods]
HPLC,NMR | [BRN ]
1499137 | [Stability:]
Moisture Sensitive | [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 | [SMILES]
C(ON1C(=O)CCC1=O)(=O)ON1C(=O)CCC1=O | [CAS DataBase Reference]
74124-79-1(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive;Store under nitrogen |
Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S37/39:Wear suitable gloves and eye/face protection . S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-21 | [TSCA ]
No | [HS Code ]
29299000 |
Hazard Information | Back Directory | [Chemical Properties]
N,N'-Disuccinimidyl carbonate is white to slightly yellow crystalline powder
| [Uses]
N,N'-Disuccinimidyl carbonate is a convenient reagent for the synthesis of N-succinimidyl esters of N-protected amino acids.
| [Uses]
N,N’Disuccinimidyl Carbonate is a commonly used reagent for the preparation of N-succinimidyl esters of N-protected amino acids, activated carbonate, synthesis of urea, carbamates and coupling of lig ands to proteins. The coupling reagent property of N,N’Disuucinimidyl Carbonate speeds up coupling process, while reduces the loss of chiral integrity.
| [Uses]
N,N'-Disuccinimidyl carbonate is used to prepare cleavable linker succinimide vinylsufonylethyl carbonate for thiol modified-DNA. It serves as a reagent for the synthesis of carbamates. Further, it is used as a coupling reagent as well as in the preparation of N-succinimidyl esters of N-protected amino acids, activated carbonate and coupling of ligand to proteins. | [Synthesis Reference(s)]
Tetrahedron Letters, 20, p. 4745, 1979 DOI: 10.1016/S0040-4039(01)86699-5 | [General Description]
N,N′-Disuccinimidyl carbonate is used for the HPLC determination of amino compounds. | [reaction suitability]
reaction type: Coupling Reactions | [Synthesis]
1. 8 kg (1.25 kmol) of N-hydroxybutanediimide is added to the reactor kettle in a single addition, stirred well, and the temperature in the kettle is maintained at -2°C to 0°C.
2. 300 kg (1.62 kmol) of tributylamine and 450 kg of tetrahydrofuran are mixed in a high level tank and then slowly added to the reactor over a period of 10 to 11 hours in an amount of 50 to 57 kg per hour, maintaining the kettle temperature at not more than 5°C.
3. Due to the exothermic nature of the reaction, after the addition of tributylamine, the reaction vessel was warmed up to room temperature and the reaction was continued for 7.5 h. A large number of white solid crystals (N,N'-disuccinimidyl carbonate) were observed to precipitate out of the reaction solution.
4. Filtration of the reaction mixture: the reaction material was homogeneously introduced into a totally closed centrifuge within 1 h and dried under N2 protection. Subsequently the solids in the centrifuge were washed in two batches with 100 kg of tetrahydrofuran solvent at about 0°C and dried to give 120 kg of wet product.
5. The wet product was dried in a vacuum oven at 40 to 45°C for 7 to 8 hours to constant weight to give 95 kg of white crystalline powder with an HPLC purity of 99.1%. The filtrate obtained by centrifugal separation was used in the next step of the reaction.
6. The centrifugal filtrate and washing solvent from step 3 were combined and introduced into a 2000 L distillation unit. The tetrahydrofuran solvent was removed under vacuum at 0 to 5°C, maintaining the kettle temperature at 40 to 42°C. 7.
7. After removal of the tetrahydrofuran, 230 kg of ethylene dichloride was added, stirred at 40°C and held at 50°C for 0.5 hours. The reaction mixture was subsequently washed three times with 160 kg of water.
8. The phases were separated and the dichloromethane phase was added to a 500 L autoclave for subsequent processing. | [References]
[1] Patent: CN104030962, 2016, B. Location in patent: Paragraph 0036-0041 |
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