10354. 9-Fluorenylmethyl Chloroformate

Nomenclature

CAS number: 28920-43-6
Carbonochloridic acid 9H-fluoren-9-ylmethyl ester; 9-fluorenylmethoxycarbonyl chloride; 9-fluorenylmethyl chlorocarbonate; Fmoc chloride; Fmoc-Cl.
C15H11ClO2; mol wt 258.70.
C 69.64%, H 4.29%, Cl 13.70%, O 12.37%.

Description and references

Reagent used to introduce the 9-fluorenylmethoxycarbonyl (Fmoc) group to protect amines and alcohols. Derivatizing agent for HPLC fluorescence detection. Prepn and use in amine protection: L. A. Carpino, G. Y. Han, J. Am. Chem. Soc. 92, 5748 (1970) DOI; eidem, J. Org. Chem. 37, 3404 (1972) DOI. Additional functional group protection: C. Gioeli, J. B. Chattopadhyaya, J. Chem. Soc. Chem. Commun. 1982, 672 DOI; T. Johnson et al., ibid. 1993, 369 DOI. Amino acid derivatization, separation, and analysis: S. Einarsson et al., J. Chromatogr. 282, 609 (1983) DOI. Review: R. L. Polt in Encyclopedia of Reagents for Organic Synthesis 4, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 2545-2548.

Chemical structure

Properties

Colorless crystals from ether, mp 61.5-63°. Corrosive. Absorption max: 267 nm (ε 20500, ethyl acetate); 264 nm (ε 19810, 30% pH 3.5 phosphate buffer in methanol). Fluorescence excitation: 206, 259 nm (acetonitrile). Fluorescence emission: 311 nm (acetonitrile). Sol in dichloromethane, tetrahydrofuran, dioxane. Store at 2-8° in absence of moisture.

Use

Reagent in synthetic organic chemistry.