Fluorenylmethyloxycarbonyl chloride

Fluorenylmethyloxycarbonyl chloride

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Ball-and-stick model of the fluorenylmethyloxycarbonyl chloride molecule
Names
IUPAC name Chloroformic acid 9H-fluoren-9-ylmethyl ester
Other names 9-Fluorenylmethyl chloroformate; 9-Fluorenylmethoxycarbonyl chloride; Fmoc-chloride
Identifiers
CAS Number	28920-43-6 Y
ChemSpider	31647 Y
Jmol 3D model	Interactive image
PubChem	34367
InChI InChI=1S/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2 Y Key: IRXSLJNXXZKURP-UHFFFAOYSA-N Y InChI=1/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2 Key: IRXSLJNXXZKURP-UHFFFAOYAT
SMILES ClC(=O)OCC3c1ccccc1c2c3cccc2
Properties
Chemical formula	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}}}
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:

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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.:

Scheme showing addition of an Fmoc group to an amino acid

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:

Mechanism of the deprotection of the Fmoc group with 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.

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.