N,N'-Disuccinimidyl carbonate Chemical Properties

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. 

-20°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.

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)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

F 

10-21

TSCA 

No

HS Code 

29299000

MSDS

• Language:English Provider:N,N'-Disuccinimidyl carbonate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

N,N'-Disuccinimidyl carbonate Usage And Synthesis

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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