Chloroformic acid 9H-fluoren-9-ylmethyl ester
9-Fluorenylmethyl chloroformate; 9-Fluorenylmethoxycarbonyl chloride; Fmoc-chloride
|Molar mass||258.70 g·mol−1|
|Melting point||62 to 64 °C (144 to 147 °F; 335 to 337 K)|
|EU classification||Corrosive (C)|
|S-phrases||S26 S36/37/39 S45|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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.
It may be cleaved by bases, typically a solution of piperidine:
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.
- Fmoc chloride at Sigma-Aldrich
- Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry 37 (22): 3404. doi:10.1021/jo00795a005.
- Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki (2008). "A solid-state 17O NMR, X-ray, and quantum chemical study of N-α-Fmoc-protected amino acids". Journal of Molecular Structure 888: 187. doi:10.1016/j.molstruc.2007.11.059.
- Paquet, A. (1982). "Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates". Canadian Journal of Chemistry 60 (8): 976. doi:10.1139/v82-146.
- J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002.