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| CAS No.: | 82911-69-1 |
|---|---|
| Name: | N-(9-Fluorenylmethoxycarbonyloxy)succinimide |
| Molecular Structure: | |
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| Formula: | C19H15NO5 |
| Molecular Weight: | 337.332 |
| Synonyms: | 9-Fluorenylmethylsuccinimidyl carbonate;2,5-Pyrrolidinedione, 1-(((9H-fluoren-9-ylmethoxy)carbonyl)oxy)-;Fmoc-OSu;N-(9-FluorenylmethoxyCar;(2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate;Fmoc-onsu;N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide;Fmoc;N-(9-FluorenylmethoxyCarbonyloxy) Succinimide;N-(9-Fluorenylmethoxycarbonyloxy)-succinimide;Fluoren-9-ylmethyl succinimidyl carbonate;Fmoc-OSu (9-Fluorenylmethyl succinimidyl carbonate);Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 9H-fluoren-9-ylmethyl ester;9-Fluorenylmethyl succinimidyl carbonate;Fmoc-ONSu;N-(9-Fluorenylmethoxycarbonyloxy) Succinimide;9-Fluorenylmethyl N-succinimidyl carbonate; |
| EINECS: | 433-520-5 |
| Density: | 1.42 g/cm3 |
| Melting Point: | 150-153 °C(lit.) |
| Boiling Point: | 494.3 °C at 760 mmHg |
| Flash Point: | 252.7 °C |
| Appearance: | White powder |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 22-24/25-26/37/39-26 |
| PSA: | 72.91000 |
| LogP: | 2.95400 |
1-hydroxy-pyrrolidine-2,5-dione
(fluorenylmethoxy)carbonyl chloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| With triethylamine In 1,4-dioxane for 1h; Ambient temperature; | 96% |
| With sodium carbonate In water; toluene at 25 - 30℃; for 2h; Reagent/catalyst; Solvent; | 56.3% |
| With sodium carbonate In water; acetone for 0.5h; Acylation; |
(fluorenylmethoxy)carbonyl chloride
dicyclohexylamine salt of N-hydroxysuccinimide
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| In chloroform | 90% |
(fluorenylmethoxy)carbonyl chloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| In chloroform | 90% |
2,5-dioxopyrrolidin-1-yl carbonochloridate
9-Fluorenylmethanol
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| With pyridine In dichloromethane for 5h; Ambient temperature; | 72% |
N-cyclohexyl-cyclohexanamine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 95 percent / acetone 2: 90 percent / CHCl3 View Scheme |
L-serin
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate | 100% |
| With sodium carbonate In 1,4-dioxane | 97% |
| With sodium hydrogencarbonate In water; acetonitrile | 94% |
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate | 100% |
| Stage #1: L-threonine; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In 1,4-dioxane; water at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=4; | 100% |
| With sodium hydrogencarbonate In acetone | 97% |
methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester
| Conditions | Yield |
|---|---|
| Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.25h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane; water at 20℃; for 14h; | 100% |
| Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.25h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane; water at 20℃; for 14h; | 100% |
| Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane at 20℃; for 0.5h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane at 20℃; for 24h; | 97% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
3-(3-(amino-4-methoxyphenylmethyl)-4-methoxyphenyl)propionic acid
3-(α-fluoren-9-ylmethoxycarbonylamino-4-methoxybenzyl)-4-methoxyphenylpropionic acid
| Conditions | Yield |
|---|---|
| With triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature; | 100% |
| Conditions | Yield |
|---|---|
| With pyridine In N,N-dimethyl-formamide at 20℃; for 18h; | 100% |
| With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 4h; | 99% |
| With pyridine In methanol; N,N-dimethyl-formamide at 20℃; for 12h; | 95% |
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The 9-Fluorenylmethyl succinimidyl carbonate, with the CAS registry number 82911-69-1, is also known as 2,5-Pyrrolidinedione, 1-(((9H-fluoren-9-ylmethoxy)carbonyl)oxy)-. It belongs to the product categories of Amino Acid Derivatives; Medical Intermediates; Benzocycles; Fluorenes, Flurenones; Pyrrolidines; N-Protecting Reagents; Biochemistry; Condensation & Active Esterification; Fluorenes; Fluorenes & Fluorenones; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Succinimides; Peptide Synthesis; Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry; Fmoc-Amino Acid Series. Its EINECS registry number is 433-520-5. This chemical's molecular formula is and molecular weight is . Its IUPAC name is called (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate.
Physical properties of 9-Fluorenylmethyl succinimidyl carbonate: (1)ACD/LogP: 2.32; (2)ACD/LogD (pH 5.5): 2.32; (3)ACD/LogD (pH 7.4): 2.32; (4)ACD/BCF (pH 5.5): 33.91; (5)ACD/BCF (pH 7.4): 33.91; (6)ACD/KOC (pH 5.5): 433.51; (7)ACD/KOC (pH 7.4): 433.51; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.661; (11)Molar Refractivity: 87.47 cm3; (12)Molar Volume: 236.4 cm3; (13)Surface Tension: 66.7 dyne/cm; (14)Density: 1.42 g/cm3; (15)Flash Point: 252.7 °C; (16)Enthalpy of Vaporization: 76.16 kJ/mol; (17)Boiling Point: 494.3 °C at 760 mmHg; (18)Vapour Pressure: 6.55E-10 mmHg at 25°C.
Preparation: this chemical can be prepared by N-hydroxy-succinimide and 9H-fluoren-9-ylmethyl chloroformate. This reaction is a kind of Acylation. It will need reagent Na2CO3 and solvent H2O, acetone. The reaction time is 30 min.
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Uses of 9-Fluorenylmethyl succinimidyl carbonate: it can be used to produce N-(9-fluorenylmethyloxycarbonyl)-L-serine methyl ester. This reaction will need reagent aq. sodium hydrogen carbonate and solvent dioxane with reaction time of 10 min. The yield is about 80%.
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When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
(2)InChI: InChI=1S/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2
(3)InChIKey: WMSUFWLPZLCIHP-UHFFFAOYSA-N
