Fluorenylmethyloxycarbonyl chloride

Fluorenylmethyloxycarbonyl chloride[1]
Identifiers
CAS number 28920-43-6 Y
PubChem 34367
ChemSpider 31647 Y
Jmol-3D images Image 1
Properties
Molecular formula C15H11ClO2
Molar mass 258.7 g mol−1
Melting point

62-64 °C

Hazards
EU classification Corrosive (C)
R-phrases R34
S-phrases S26 S36/37/39 S45
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

  1. ^ Fmoc chloride at Sigma-Aldrich
  2. ^ Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry 37 (22): 3404. doi:10.1021/jo00795a005. 
  3. ^ 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. 
  4. ^ 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. http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=60&issue=8&startPage=976. 
  5. ^ J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002.