N,N'-Disuccinimidyl carbonate

Iupac Name：bis(2,5-dioxopyrrolidin-1-yl) carbonate

Molecular Weight：256.17 .

Modify Date.: 2022-11-07 10:18

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: N,N'-Disuccinimidyl carbonate
1.2 Synonyms: 1,1'-[Carbonylbis(oxy)]di(2,5-pyrrolidinedione) 1,1'-[Carbonylbis(oxy)]dipyrrolidine-2,5-dione 2,5-PYRROLIDINEDIONE, 1,1'-[CARBONYLBIS(OXY)]BIS- bis(2,5-dioxopyrrolidin-1-yl) carbonate Carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester Carbonic acid, bis(2,5-dioxo-1-pyrrolidinyl) ester DI-(N,N'-SUCCINIMIDYL) CARBONATE FOR SYN di-N,N'-succnimidly carbonat DISUCCINIMIDYL CARBONATE DSC EINECS 277-730-3 MFCD00009767 N,N-DisucciniMdyl carbonate N,N'-Disuccinimidylcarbonate N,Nzzhlxy-Disuccinimidyl carbonate (DSC) N-Succinimidyl Carbonate N,N'-Disuccinimidyl Carbonate DSC

1.3 CAS No.: 74124-79-1

1.4 CID: 676246

1.5 EINECS(EC#): 277-730-3

1.6 Molecular Formula: C9H8N2O7 (isomer)

1.7 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

1.8 InChkey: PFYXSUNOLOJMDX-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O

1.10 Isomers Smiles: C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O

2. Properties

2.1 Density: 1.69

2.1 Melting point: 190℃

2.1 Boiling point: 383.7°C at 760 mmHg

2.1 Refractive index: 1.596

2.1 Flash Point: 185.9°C

2.1 Precise Quality: 256.03300

2.1 PSA: 110.29000

2.1 logP: -0.85660

2.1 Appearance: white crystals

2.2 Storage: Keep Cold. Hygroscopic. Store under Nitrogen.

2.3 Chemical Properties: N,N'-Disuccinimidyl carbonate is white to slightly yellow crystalline powder

2.4 Color/Form: White to slightly yellow

2.5 Water Solubility: Decomposes

2.6 Stability: Stable at room temperature in closed containers under normal storage and handling conditions. Moisture sensitive.

2.7 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H302; H315; H319; H335

4.1 RIDADR: 20kgs

4.1 Caution Statement: P301 + P312 + P330-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes:?Xn,Xi
The Risk Statements:
R22:? Harmful if swallowed?
R36/37/38:? Irritating to eyes, respiratory system and skin?
The Safety Statements:
S26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
S36:? Wear suitable protective clothing?
S37/39:? Wear suitable gloves and eye/face protection?
WGK Germany:3
F:10-21

4.2 Specification: ? N,N'-Disuccinimidyl carbonate (CAS NO.74124-79-1), its Synonyms are Di(succinimido) carbonate ; DSC ; N-Succinimidyl carbonate ; Bis (N-succinimidyl) carbonate ; Di(succinimido) carbonate . It is white to slightly yellow crystalline powder.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

74124-79-1Total: 2 Synthesis Route

6066-82-6 454 Suppliers

503-38-8 29 Suppliers

74124-79-1 231 Suppliers

Literatures:
Ogura; Haruo Patent: US4341707 A1, 1982 ;
Yield: ~78%

6066-82-6 454 Suppliers

32315-10-9 149 Suppliers

74124-79-1 231 Suppliers

Literatures:
Konakahara; Ozaki; Sato; Gold Synthesis, 1993 , # 1 p. 103 - 106
Yield: ~95%

8. Precursor and Product

precursor:

6066-82-6

503-38-8

32315-10-9

product :

173601-02-0

80354-49-0

80354-45-6

96-31-1

35013-72-0

88692-23-3

88692-21-1

120-93-4

13139-17-8

80672-61-3

2214-72-4

3397-30-6

128595-07-3

2387-23-7

38862-25-8

117032-51-6

103835-64-9

13149-88-7

16328-62-4

18342-66-0

334616-59-0

22794-66-7

444288-94-2

934-34-9

10276-85-4

615-16-7

View all

9. Other Information

9.0 Usage: 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.

9.1 BRN: 1499137

9.2 Chemical Properties: N,N'-Disuccinimidyl carbonate is white to slightly yellow crystalline powder

9.3 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.

9.4 Uses: N,N'-Disuccinimidyl carbonate is a convenient reagent for the synthesis of N-succinimidyl esters of N-protected amino acids.

9.5 Synthesis Reference(s): Tetrahedron Letters, 20, p. 4745, 1979 DOI: 10.1016/S0040-4039(01)86699-5

9.6 General Description: N,N′-Disuccinimidyl carbonate is used for the HPLC determination of amino compounds.

10. Computational chemical data

Molecular Weight: 256.17 .g/mol
Molecular Formula: C₉H₈N₂O₇
Compound Is Canonicalized: True
XLogP3-AA: -1.3
Exact Mass: 256.03315060
Monoisotopic Mass: 256.03315060
Complexity: 386
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 110
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzOAAAAAAAAAAAAAAAAAAAAWLAAAAAAAAAAAAAAAAAAAAAHgAEAAAACACBgAAACAIQAAAIAAEQGAAAAAAAAAAgAAEAAAAAABAAgAAEAAAABCCAAAAFAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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N,N'-Disuccinimidyl carbonate