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CAS No.: | 74124-79-1 |
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Name: | N,N'-Disuccinimidyl carbonate |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C9H8N2O7 |
Molecular Weight: | 256.172 |
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; |
EINECS: | 277-730-3 |
Density: | 1.69 g/cm3 |
Melting Point: | 190 °C |
Boiling Point: | 383.7 °C at 760 mmHg |
Flash Point: | 185.9 °C |
Solubility: | Soluble in dimethyl sulfoxide, hot pyridine, acetonitrile and most organic solvents. Insoluble in water. |
Appearance: | white to slightly yellow crystalline powder |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-36/37/38 |
Safety: | 26-37/39 |
PSA: | 110.29000 |
LogP: | -0.85660 |
1-hydroxy-pyrrolidine-2,5-dione
bis(trichloromethyl) carbonate
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% |
1-hydroxy-pyrrolidine-2,5-dione
trichloromethyl chloroformate
di(succinimido) carbonate
Conditions | Yield |
---|---|
80% |
1-hydroxy-pyrrolidine-2,5-dione
(fluorenylmethoxy)carbonyl chloride
A
di(succinimido) carbonate
B
9-fluorenylmethyl N-succinimidyl carbonate
Conditions | Yield |
---|---|
With tributyl-amine In tetrahydrofuran at -2 - 5℃; Temperature; Large scale; | A 95 kg B 119 kg |
di(succinimido) carbonate
4-(benzyloxycarbonylamino)butyric acid
N-hydroxysuccinimide ester of 4-<(carbobenzyloxy)amino>butyric acid
Conditions | Yield |
---|---|
With pyridine | 100% |
di(succinimido) carbonate
Boc-Lys(Boc)-OH
N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester
Conditions | Yield |
---|---|
With pyridine | 100% |
di(succinimido) carbonate
(S)-3-hydroxytetyrahydrofurane
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% |
di(succinimido) carbonate
2-(2-tert-butyloxycarbonylaminoethoxy)ethanol
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% |
di(succinimido) carbonate
1,12-dodecanedioic acid
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% |
di(succinimido) carbonate
cyclohexylmethyl alcohol
N-succinimidyl carbonic acid cyclohexylmethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 100% |
di(succinimido) carbonate
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% |
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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%.
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%.
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