[A11683] CAS 28920-43-6 | 9-Fluorenylmethyl chloroformate, 98+%

CAS : 28920-43-6
UN# : UN2928
MDL : MFCD00001138
Hazard Class : 6.1
EINECS : 249-313-6
Packing Group : II

Other name :

Chloroformic acid 9-fluorenylmethyl esterFmoc-Cl

Chemical Properties

Formula : C15H11ClO2
Formula weight : 258.70
Melting Point : 60-64°
Sensitivity : Keep Cold. Moisture Sensitive. Store under Nitrogen.
Form : Crystalline powder
Solubility : Soluble in dioxane.

Literature References

Reagent for the protection of amino groups in peptide synthesis (see Appendix 6) as their 9-fluorenylmethoxycarbonyl (Fmoc) derivatives: J. Org. Chem., 37, 3404 (1972); J. Am. Chem. Soc., 96, 4987 (1974); 99, 7363 (1977). Review: Acc. Chem. Res., 20, 401 (1987). They are particularly applicable in solid-phase peptide synthesis. The stability of Fmoc-protected amino acids to acidic conditions permits their conversion in many cases to the acid chlorides as active intermediates for peptide coupling, resistant to racemization, in contrast to other protected amino acid chlorides. For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996). In the presence of triethylamine, reacts with Pentafluorophenol, A15574, to give the PFP carbonate, a useful active ester for the preparation of Fmoc-amino acids. Moreover, the active PFP ester of the protected amino acid can be obtained by in situ DCC coupling with the liberated PFP: Synthesis, 303 (1986). Cleavage of the Fmoc group occurs under mildly basic conditions: Ethanolamine: J. Am. Chem. Soc., 92, 5748 (1970); J. Org. Chem., 37, 3404 (1972). Piperidine: J. Org. Chem., 52, 1197 (1987); applicable to solid-phase peptide synthesis. TBAF in DMF; rapid reaction at room temperature: Tetrahedron Lett., 28, 6617 (1987). For both the deblocking of Fmoc-protected amino acids and for the removal of excess reagent during the protection step, 4-(Aminomethyl)­piperidine, L11577, has been recommended: J. Org. Chem., 51, 3732 (1986); 55, 721 (1990), particularly in conjunction with Fmoc-protected acid chlorides as the active species. Even better results have been obtained with Tris(2-aminoethyl)­amine, B21789, in this type of chemistry: J. Org. Chem., 55, 1673 (1990). Limited use has also been made in the protection of alcohols as 9-fluorenylmethyl carbonates, rapidly cleaved by triethylamine: J. Chem. Soc., Chem. Commun., 672 (1982).

Notes

Moisture sensitive. Store in a cool place. Incompatible with alcohols and amines.Other References:Beilstein: 2279177UN#: UN2928

Grade Specifications

Grade Specifications

Hazard Statements : H301-H331-H314-H318Toxic if swallowed.Toxic if inhaled.Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501aDo not breathe dust/fume/gas/mist/vapours/spray.IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.