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| CAS No.: | 13139-17-8 |
|---|---|
| Name: | N-(Benzyloxycarbonyloxy)succinimide |
| Article Data: | 25 |
| Molecular Structure: | |
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| Formula: | C12H11NO5 |
| Molecular Weight: | 249.223 |
| Synonyms: | Succinimide, N-(carboxyoxy)-, benzyl ester(8CI);1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione;Benzyl2,5-dioxopyrrolid-1-yl carbonate;Benzyl N-succinimidyl carbonate;Benzyl succinimidyl carbonate;N-(N-Benzyloxycarbonyloxy)succinimide;N-Benzyloxycarbonyloxysuccinamide;Benzyloxycarbonyloxysuccinimide;Z-OSu;Cbz-OSu; |
| EINECS: | 236-075-3 |
| Density: | 1.38 g/cm3 |
| Melting Point: | 80-82 °C(lit.) |
| Boiling Point: | 369 °C at 760 mmHg |
| Flash Point: | 177 °C |
| Solubility: | acetone: 0.1 g/mL, clear |
| Appearance: | white crystal powde |
| Hazard Symbols: |
 Xi, Xn
|
| Risk Codes: | 43-24/25-36/37/38-20/21/22 |
| Safety: | 22-24/25-36-26 |
| PSA: | 72.91000 |
| LogP: | 1.34170 |
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- 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione
- 501-53-1
benzyl chloroformate
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In water; ethyl acetate at 15℃; for 19h; Large scale; | 90.5% |
| With TEA In 1,2-dimethoxyethane | 25% |
| With triethylamine In acetonitrile at 5℃; for 1h; |
- 82911-72-6
dicyclohexylamine salt of N-hydroxysuccinimide
- 501-53-1
benzyl chloroformate
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| In chloroform | 90% |
- 108-30-5
succinic acid anhydride
- 501-53-1
benzyl chloroformate
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| Stage #1: succinic acid anhydride With hydroxylamine sulfate In water Alkaline conditions; Stage #2: With phosphoric acid In water; toluene Reflux; Alkaline conditions; Stage #3: benzyl chloroformate In toluene for 2h; Reagent/catalyst; | 52.7% |
- 74124-79-1
di(succinimido) carbonate
- 100-51-6
benzyl alcohol
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile at 20℃; Substitution; | |
| With triethylamine In acetonitrile at 20℃; for 0.75 - 1h; Product distribution / selectivity; |
- 101-83-7
N-cyclohexyl-cyclohexanamine
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 95 percent / acetone 2: 90 percent / CHCl3 View Scheme |
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
- 199609-28-4
5-Carbamimidoyl-1H-indole-2-carboxylic acid ethyl ester
- 199609-35-3
5-(Benzyloxycarbonylamino-imino-methyl)-1H-indole-2-carboxylic acid ethyl ester
| Conditions | Yield |
|---|---|
| With triethylamine In N,N-dimethyl-formamide Ambient temperature; | 100% |
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
- 141-43-5
ethanolamine
- 77987-49-6
benzyl 2-hydroxyethylcarbamate
| Conditions | Yield |
|---|---|
| With sodium carbonate In water; acetone at 20℃; for 4h; | 100% |
| With TEA In tetrahydrofuran for 5h; | 92% |
| In 1,4-dioxane; water for 12h; | 89% |
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
- 2508-29-4
5-hydroxypentylamine
- 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water; acetone at 20℃; for 4h; | 100% |
| In tetrahydrofuran at 20℃; for 19h; Acylation; |
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
- 103639-57-2
(2S)-2-(2-methoxyethyl)piperidine
- 190967-63-6
benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 23℃; for 18h; | 100% |
- 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide
- 13325-10-5
4-Aminobutanol
- 17996-13-3
benzyl 4-hydroxybutylcarbamate
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In water; acetone at 20℃; for 4h; | 100% |
| With triethylamine In acetone at 20℃; for 7h; | 92.8% |
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Specification
The N-(Benzyloxycarbonyloxy)succinimide, with the cas registry number 13139-17-8, has the systematic name of 1-{[(benzyloxy)carbonyl]oxy}pyrrolidine-2,5-dione and the IUPAC name of benzyl (2,5-dioxopyrrolidin-1-yl) carbonate. This chemical is a kind of white crystal powde and it is sensitive.
The followings are the basic information of this chemical: Its product categories are various, including peptide coupling agents; amino acid derivatives; medical intermediates; imidazoles, pyrroles, pyrazoles, pyrrolidines; n-protecting reagents; biochemistry; condensation & active esterification; n-substituted maleimides, succinimides & phthalimides; n-substituted succinimides; peptide synthesis. As to its usage, it is usually used to be polypeptide reagent.
The characteristics of this chemical are as follows: (1)ACD/LogP: 0.42; (2)ACD/LogD (pH 5.5): 0.42; (3)ACD/LogD (pH 7.4): 0.42; (4)ACD/BCF (pH 5.5): 1.23; (5)ACD/BCF (pH 7.4): 1.23; (6)ACD/KOC (pH 5.5): 40.42; (7)ACD/KOC (pH 7.4): 40.42; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 72.91; (11)Index of Refraction: 1.583; (12)Molar Refractivity: 60.2 cm3; (13)Molar Volume: 180 cm3; (14)Polarizability: 23.86 ×10-24 cm3; (15)Surface Tension: 58 dyne/cm; (16)Density: 1.38 g/cm3; (17)Flash Point: 177 °C; (18)Enthalpy of Vaporization: 61.57 kJ/mol; (19)Boiling Point: 369 °C at 760 mmHg; (20)Vapour Pressure: 1.23E-05 mmHg at 25°C; (21)Exact Mass: 249.063722; (22)MonoIsotopic Mass: 249.063722; (23)Topological Polar Surface Area: 72.9; (24)Heavy Atom Count: 18; (25)Complexity: 332.
The production method is as below: carbonochloridic acid benzyl ester could react with dicyclohexylamine salt of N-hydroxysuccinimide to produce N-(Benzyloxycarbonyloxy)succinimide, with the following condition: solution: CHCl3; yield: 90%.
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Use of N-(Benzyloxycarbonyloxy)succinimide is as below: N-(Benzyloxycarbonyloxy)succinimide could react with L-serine to produce N-benzyloxycarbonyl-L-serine, with the following condition: reagent:sodium bicarbonate; solution: H2O and acetone; yield: 92% .
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When dealing with this chemical, you should be cautious and then take some measures to protect yourself. Being irritant to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes, and it may cause sensitisation by skin contact. If by inhalation, in contact with skin or if swallowed, it will be very harmful. Therefore, you should take the following instructions. Wear suitable protective clothing and avoid contacting with skin and eyes. If in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Then remember not to breathe dust while using .
Additionally, the following data information could be converted into the molecular structure:
(1)SMILES:O=C2N(OC(=O)OCc1ccccc1)C(=O)CC2
(2)InChI:InChI=1/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2