物质信息
ID:715103
名称和标识
别名
FMOC-Cl9-Fluorenylmethyl chloroformate9-氯甲酸芴甲酯Chloroformic acid 9-fluorenylmethyl ester
IUPAC标准名
9H-fluoren-9-ylmethyl chloroformate
IUPAC传统名
9H-fluoren-9-ylmethyl chloroformate
化合物性质
安全信息
欧盟危险性物质标志
腐蚀性 (C)
有害性 (X)TSCA收录
否
GHS警示性声明
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
危险公开号
20/22-34
联合国危险货物包装类别(PG)
II
GHS危险声明
H301-H331-H314-H318
安全公开号
26-36/37/39-45
GHS危险品标识
腐蚀金属，类别1
腐蚀皮肤，类别1A，1B，1C
严重眼损伤，类别1
急性毒性（口服，皮肤接触，吸入），类别1,2,3
RTECS编号
LQ6250000
保存注意事项
Moisture Sensitive
联合国危险货物等级
8
联合国危险货物编号
UN2923
理化性质
熔点
60-64°C
产品相关信息
纯度
98%
描述信息
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分子图谱
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参考文献
• 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).
• Cleavage of the Fmoc group occurs under mildly basic conditions:
• 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).
• 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.
• 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).
• 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).