ChemicalBook > CAS DataBase List > N,N'-Disuccinimidyl carbonate

N,N'-Disuccinimidyl carbonate

Product Name
N,N'-Disuccinimidyl carbonate
CAS No.
74124-79-1
Chemical Name
N,N'-Disuccinimidyl carbonate
Synonyms
DSC;Bis(2,5-dioxopyrrolidin-1-yl) carbonate;DISUCCINIMIDYL CARBONATE;SU2O;DI(SUCCINIMIDO) CARBONATE;DI(N-SUCCINIMIDYL) CARBONATE;BIS(N-SUCCINIMIDYL) CARBONATE;Carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester;(SUO)2CO;DSCsee24500
CBNumber
CB3323388
Molecular Formula
C9H8N2O7
Formula Weight
256.17
MOL File
74124-79-1.mol
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N,N'-Disuccinimidyl carbonate Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.51005
Product name
DSC
Purity
N,N′-Disuccinimidyl carbonate Novabiochem?
Packaging
25g
Price
$228
Updated
2025/07/31
Sigma-Aldrich
Product number
8.51005
Product name
DSC
Purity
N,N′-Disuccinimidyl carbonate Novabiochem?
Packaging
100g
Price
$678
Updated
2025/07/31
Sigma-Aldrich
Product number
8.14971
Product name
Di-(N,N′-succinimidyl) carbonate
Purity
for synthesis
Packaging
5G
Price
$177
Updated
2025/07/31
Sigma-Aldrich
Product number
225827
Product name
N,N′-Disuccinimidyl carbonate
Purity
≥95%
Packaging
1g
Price
$41.99
Updated
2025/07/31
Sigma-Aldrich
Product number
225827
Product name
N,N′-Disuccinimidyl carbonate
Purity
≥95%
Packaging
5g
Price
$114
Updated
2025/07/31
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N,N'-Disuccinimidyl carbonate Chemical Properties,Usage,Production

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

6066-82-6

28920-43-6

74124-79-1

102774-86-7

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

N,N'-Disuccinimidyl carbonate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N,N'-Disuccinimidyl carbonate manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
N,N'-Disuccinimidyl carbonate 74124-79-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-05
Henan Aochuang Chemical Co.,Ltd.
Product
N,N'-Disuccinimidyl carbonate 74124-79-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-26
Shaanxi Didu New Materials Co. Ltd
Product
N,N'-Disuccinimidyl Carbonate 74124-79-1
Price
US $80.00/kg
Min. Order
1kg
Purity
99.0% Min
Supply Ability
100 Tons
Release date
2025-03-27

74124-79-1, N,N'-Disuccinimidyl carbonateRelated Search:

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  • 2,5-PYRROLIDINEDIONE, 1,1'-[CARBONYLBIS(OXY)]BIS-
  • di-N,N'-succnimidly carbonat
  • Carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester
  • N,Nzzhlxy-Disuccinimidyl carbonate (DSC)
  • Carbonic acid, bis(2,5-dioxo-1-pyrrolidinyl) ester
  • N-Succinimidyl Carbonate N,N'-Disuccinimidyl Carbonate DSC
  • DI-(N,N'-SUCCINIMIDYL) CARBONATE FOR SYN
  • N,N-DisucciniMdyl carbonate
  • Bis(2,5-dioxopyrrolidin-1-yl) carbonate 98%
  • N,N'-Disuccinimidyl carbonate, DSC, 1,1'-[Carbonylbis(oxy)]dipyrrolidine-2,5-dione
  • N,N'-DisucciniMidyl carbonate >=95%
  • N,N'-DisucciniMidyl carbonate puruM, >=95.0% (NMR)
  • <i>N</i>,<i>N</i>′-Disuccinimidyl carbonate
  • 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
  • N,N'-Disuccinimidyl carbonate, tech. 85%, remainder N-hydroxysuccinimide
  • N-Succinimidyl carbonate, Di(N-succinimidyl) carbonate, DSC
  • Bis(2,5-dioxopyrrolidin-1-yl) carbonate
  • N,N'-Disuccinimidyl carbonate ,99%
  • 1,1'-(Carbonylbisoxy)bis(pyrrolidine-2,5-dione)
  • 1,1'-[Carbonylbis(oxy)]bis(2,5-pyrrolidinedione)
  • Carbonic acid bis(succinimidyl) ester
  • N,N'-(Carbonylbisoxy)bissuccinimide
  • DSC (Di(N-succinimidyl)carbonate
  • 1,1''-[CARBONYLBIS(OXY)]DIPYRROLIDINE-2,5-DIONE
  • Disuccinimidyl carbonate, Su2O
  • DSC (Di(N-succinimidyl)carbonate: N-Succinimidyl carbonate)
  • N,N'-Disuccinimidyl carbonate≥ 99% (HPLC)
  • DSC N,N'-Disuccinimidyl carbonate Novabiochem
  • Di-(N,N'-succinimidyl) carbonate for synthesis
  • TIMTEC-BB SBB005976
  • SU2O
  • (SUO)2CO
  • BIS(N-SUCCINIMIDYL) CARBONATE
  • DSC
  • DI(SUCCINIMIDO) CARBONATE
  • DISUCCINIMIDYL CARBONATE
  • DI-(N,N'-SUCCINIMIDYL) CARBONATE
  • DI(N-SUCCINIMIDYL) CARBONATE
  • LABOTEST-BB LT00847311
  • N-SUCCINIMIDYL CARBONATE
  • N'-Disuccinimidyl carbonate
  • Di(N-succinimidyl)Carbonate&gt
  • N,N''-Disuccinimidyl carbonate, Tech Grade
  • N,N'-Disuccinimidyl carbonate USP/EP/BP
  • N,N′-Disuccinimidyl Carbonate (Technical Grade)
  • Di-(N-Succinimidyl) Carbonate extrapure, 95%
  • N. N '- Disuccinimide carbonate
  • N,N' -dissuccinimide carbonate
  • N,N'-Disuccinimidyl carbonate
  • DSCN,N'-Disuccinimidyl carbonate
  • N,N'-Disuccinimidyl Carbonate（DSC）
  • N,N''-Disuccinimidyl carbonate (DSC)