Fluorenylmethyloxycarbonyl chloride
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| Ball-and-stick model of the fluorenylmethyloxycarbonyl chloride molecule | |
| Names | |
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| IUPAC name
Chloroformic acid 9H-fluoren-9-ylmethyl ester
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| Other names
9-Fluorenylmethyl chloroformate; 9-Fluorenylmethoxycarbonyl chloride; Fmoc-chloride
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| Identifiers | |
28920-43-6  |
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| ChemSpider | 31647 |
| Jmol 3D model | Interactive image |
| PubChem | 34367 |
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| Properties | |
| C15H11ClO2 | |
| Molar mass | 258.70 g·mol−1 |
| Melting point | 62 to 64 °C (144 to 147 °F; 335 to 337 K) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Fluorenylmethyloxycarbonyl chloride (FMOC-Cl) is a chloroformate ester. It is used to introduce FMOC group as the FMOC carbamate.
Preparation
This compound may be prepared by reacting 9-fluorenylmethanol with phosgene:[2]
Reactions
The FMOC carbamate is often used as a protecting group for amines. The FMOC group can be introduced by reacting the amine with FMOC-Cl, e.g.:[3]
The other common method for introducing the FMOC group is through 9-fluorenylmethyl succinimidyl carbonate (FMOC-OSu), which may itself be obtained by the reaction of FMOC-Cl with the dicyclohexylammonium salt of N-hydroxysuccinimide.[4]
It may be cleaved by bases, typically a solution of piperidine:
FMOC protection has found significant use in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin.[5]
Because the fluorenyl group is highly fluorescent, certain UV-inactive compounds may be reacted to give the FMOC derivatives, suitable for analysis by reversed phase HPLC. Analytical uses of FMOC-Cl that do not use chromatography may be limited by the requirement that excess FMOC-Cl be removed before an analysis of fluorescence.
References
- ↑ Fmoc chloride at Sigma-Aldrich
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- ↑ J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002.
