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Cas Database |
| Name |
N,N'-Disuccinimidyl carbonate |
EINECS | 277-730-3 |
| CAS No. | 74124-79-1 | Density | 1.69 g/cm3 |
| PSA | 110.29000 | LogP | -0.85660 |
| Solubility | Soluble in dimethyl sulfoxide, hot pyridine, acetonitrile and most organic solvents. Insoluble in water. | Melting Point |
190 °C |
| Formula | C9H8N2O7 | Boiling Point | 383.7 °C at 760 mmHg |
| Molecular Weight | 256.172 | Flash Point | 185.9 °C |
| Transport Information | N/A | Appearance | white to slightly yellow crystalline powder |
| Safety | 26-37/39 | Risk Codes | 22-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xn,  Xi
|
| Synonyms |
Disuccinimidyl carbonate;Disuccininidyl carbonate;N,N'-Disuccinimido carbonate;Carbonic acid,bis(2,5-dioxo-1-pyrrolidinyl) ester;2,5-Pyrrolidinedione,1,1'-[carbonylbis(oxy)]bis- (9CI);1-[[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]-2,5-pyrrolidinedione;Bis(N-succinimidyl) carbonate;Bis(succinimidyl) carbonate;Carbonic acidbis(2,5-dioxopyrrolidin-1-yl) ester;Di-(2,5-dioxopyrrolidin-1-yl)carbonate;Disuccimidyl carbonate; |
Article Data | 8 |
N,N'-Disuccinimidyl carbonate Synthetic route
- 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione
- 32315-10-9
bis(trichloromethyl) carbonate
- 74124-79-1
di(succinimido) carbonate
| Conditions | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine In dichloromethane 1.) 0 deg C, 3 h, 2.) 0-20 deg C, 6 h, 3.) reflux, 2 h; | 94% |
| With tributyl-amine In tetrahydrofuran for 14h; Ambient temperature; | 89% |
| With Pinene In tetrahydrofuran for 12h; Heating; | 76% |
- 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione
- 503-38-8
trichloromethyl chloroformate
- 74124-79-1
di(succinimido) carbonate
| Conditions | Yield |
|---|---|
| 80% |
- 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
A
- 74124-79-1
di(succinimido) carbonate
B
- 102774-86-7
9-fluorenylmethyl N-succinimidyl carbonate
| Conditions | Yield |
|---|---|
| With tributyl-amine In tetrahydrofuran at -2 - 5℃; Temperature; Large scale; | A 95 kg B 119 kg |
- 74124-79-1
di(succinimido) carbonate
- 5105-78-2
4-(benzyloxycarbonylamino)butyric acid
- 60722-88-5
N-hydroxysuccinimide ester of 4-<(carbobenzyloxy)amino>butyric acid
| Conditions | Yield |
|---|---|
| With pyridine | 100% |
- 74124-79-1
di(succinimido) carbonate
- 2483-46-7
Boc-Lys(Boc)-OH
- 30189-36-7
N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester
| Conditions | Yield |
|---|---|
| With pyridine | 100% |
- 74124-79-1
di(succinimido) carbonate
- 86087-23-2
(S)-3-hydroxytetyrahydrofurane
- 138499-08-8
1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile at 20℃; for 18h; | 100% |
| With triethylamine In acetonitrile at 20℃; for 18h; | 100% |
| With triethylamine In acetonitrile at 20℃; for 21.5h; | 94% |
- 74124-79-1
di(succinimido) carbonate
- 139115-91-6
2-(2-tert-butyloxycarbonylaminoethoxy)ethanol
- 261364-63-0
tert-butyl (2-(2-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)ethoxy)ethyl)carbamate
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile at 20℃; for 2h; | 100% |
| With pyridine In chloroform at 25 - 30℃; Acylation; | 96% |
| With triethylamine In acetonitrile at 40℃; for 1h; | 70% |
- 74124-79-1
di(succinimido) carbonate
- 693-23-2
1,12-dodecanedioic acid
- 75472-90-1
dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester
| Conditions | Yield |
|---|---|
| With pyridine In acetonitrile at 20℃; for 7h; | 100% |
| With pyridine In acetonitrile at 20℃; for 7h; Inert atmosphere; | 100% |
| With pyridine In acetonitrile at 20℃; for 3h; | 90% |
- 74124-79-1
di(succinimido) carbonate
- 100-49-2
cyclohexylmethyl alcohol
- 922723-33-9
N-succinimidyl carbonic acid cyclohexylmethyl ester
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 20℃; | 100% |
- 74124-79-1
di(succinimido) carbonate
- 1017575-24-4
benzyl (4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepane-1-carboxylate
| Conditions | Yield |
|---|---|
| Stage #1: C5H7NO3*C14H20N2O2 With triethylamine In acetonitrile at 5℃; Stage #2: di(succinimido) carbonate In acetonitrile at 2 - 2.5℃; for 0.833333h; | 100% |
N,N'-Disuccinimidyl carbonate Specification
The systematic name of N,N'-Disuccinimidyl carbonate is 1,1'-[carbonylbis(oxy)]dipyrrolidine-2,5-dione. With the CAS registry number 74124-79-1, it is also named as Di(succinimido) carbonate. The product's categories are Medical Intermediates; Coupling Reagent; N-Protecting Reagents; Biochemistry; Condensation & Active Esterification; Coupling Reactions (Peptide Synthesis); N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Succinimides; Peptide Synthesis; Synthetic Organic Chemistry; Amino Ester. It is white to slightly yellow crystalline powder which should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -3.06; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 9; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 110.29 Å2; (7)Index of Refraction: 1.596; (8)Molar Refractivity: 51.45 cm3; (9)Molar Volume: 151 cm3; (10)Polarizability: 20.39×10-24 cm3; (11)Surface Tension: 79.2 dyne/cm; (12)Flash Point: 185.9 °C; (13)Enthalpy of Vaporization: 63.23 kJ/mol; (14)Boiling Point: 383.7 °C at 760 mmHg; (15)Vapour Pressure: 4.31E-06 mmHg at 25°C.
Preparation of N,N'-Disuccinimidyl carbonate: It can be obtained by N-hydroxy-succinimide and carbonic acid bis-trichloromethyl ester. This reaction needs reagent i-Pr2EtN and solvent acetonitrile CH2Cl2. The yield is 94%.
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Uses of N,N'-Disuccinimidyl carbonate: It is used as dehydrating agent and pharmaceutical intermediate. It also can react with 2-amino-pyridin-3-ol to get 3H-oxazolo[4,5-b]pyridin-2-one. This reaction needs solvent acetonitrile at ambient temperature. The reaction time is 8 hours. The yield is 78%.
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When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C2N(OC(=O)ON1C(=O)CCC1=O)C(=O)CC2
2. InChI:InChI=1/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2
3. InChIKey:PFYXSUNOLOJMDX-UHFFFAOYAN
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