9-氯甲酸芴甲酯

• 产品号: A11683
• CAS号: 28920-43-6
• 分子式: C15H11ClO2
• 分子量: 258.69964
• 纯 度: 98%

产品别名

• 标题: 9-Fluorenylmethyl chloroformate
• IUPAC标准名: 9H-fluoren-9-ylmethyl chloroformate
• IUPAC传统名: 9H-fluoren-9-ylmethyl chloroformate
• 别名: Chloroformic acid 9-fluorenylmethyl ester; FMOC-Cl

产品登记号

• Beilstein号: 2279177
• CAS号: 28920-43-6
• EC号: 249-313-6
• MDL号: MFCD00001138

产品性质

• 纯度: 98%
• 熔点: 60-64°C
• GHS危险声明: H301-H331-H314-H318
• 欧盟危险性物质标志: X
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 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
• RTECS编号: LQ6250000
• 安全公开号: 26-36/37/39-45
• 保存注意事项: Moisture Sensitive
• TSCA收录: 否
• 联合国危险货物等级: 8
• 联合国危险货物编号: UN2923
• 联合国危险货物包装类别(PG): II

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).
• 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).