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28920-43-6 - 9-Fluorenylmethyl chloroformate, 98+% - Chloroformic acid 9-fluorenylmethyl ester - Fmoc-Cl - A11683 - Alfa Aesar

A11683 9-Fluorenylmethyl chloroformate, 98+%

Codice CAS
28920-43-6
Sinonimi
Chloroformic acid 9-fluorenylmethyl ester
Fmoc-Cl

Dimensioni Prezzo ($) Quantità Disponibilità
1g 17,20
5g 58,50
25g 266,00
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9-Fluorenylmethyl chloroformate, 98+%

MDL
MFCD00001138
EINECS
249-313-6

Proprietà chimiche

Formula
C15H11ClO2
Peso formula
258.70
Punto di fusione
60-64°
Sensibilità
Moisture Sensitive
Solubilità
Soluble in dioxane.

Applicazioni

Base sensitive amino protecting group for solid-phase peptide synthesis9-Fluorenylmethyl chloroformate is used in capillary electrophoresis. It acts as a reagent in the precolumn derivatization of amines for HPLC and fluorescent detection. Further, it is used for derivatizing amino acids for HPLC analysis. In addition to this, it is used to prepare N-Fmoc amino acids for solid-phase peptide synthesis and oligonucleotide synthesis.

Note

Moisture sensitive. Store in a cool place. Incompatible with alcohols and amines.

Letteratura

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).

Zhou, Y.; Lin, Q.; Jin, C.; Cheng, L.; Zheng, X.; Dai, M.; Zhang, Y. Simultaneous Analysis of N-epsilon-(Carboxymethyl) Lysine and N-epsilon-(Carboxyethyl) Lysine in Foods by Ultra-Performance Liquid Chromatography-Mass Spectrometry with Derivatization by 9-Fluorenylmethyl Chloroformate. J. Food Sci. 2015, 80 (2), C207-C217.

Boonchiangma, S.; Ratchakrut, P.; Chanthai, S.; Srijaranai, S. Reversed Phase Chromatographic Analysis of 13 Amino Acids in Honey Samples. Chromatographia 2015, 78 (13), 923-927.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H332-H314-H318

Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
2279177
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2915.90
TSCA
No
RTECS
LQ6250000

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