9H-fluoren-9-ylmethyl chloroformate

• ChemBase编号: 76540
• 分子式: C15H11ClO2
• 平均质量: 258.69964
• 单一同位素质量: 258.04475727
• SMILES: O(CC1c2c(cccc2)c2c1cccc2)C(=O)Cl
• Canonical SMILES: ClC(=O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
• InChIKey: IRXSLJNXXZKURP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 9H-fluoren-9-ylmethyl chloroformate
• IUPAC传统名: 9H-fluoren-9-ylmethyl chloroformate
• 别名: 9-氯甲酸芴甲酯; 9-芴甲氧羰酰氯; 芴甲氧羰酰氯; 氯甲酸-9-芴基甲酯; Chloroformic acid 9-fluorenylmethyl ester; 9-Fluorenylmethyl chloroformate; 9H-fluoren-9-ylmethyl chloridocarbonate; Fmoc chloride; (9H-Fluoren-9-yl)methyl carbonochloridoate; (9H-Fluoren-9-yl)methyl chloroformate; FMOC-Cl; 9-Fluorenylmethoxycarbonyl chloride; Fmoc chloride; 9-FLUORENYLMETHYL CHLOROFORMATE; 9-Fluorenylmethyl chloroformate; Fmoc-chloride; Fluorenylmethyloxycarbonyl chloride

登记号

• CAS号: 28920-43-6
• EC号: 249-313-6
• MDL号: MFCD00001138
• Beilstein号: 2279177
• PubChem SID: 162041444; 24849875; 24853862; 24853863
• PubChem CID: 34367
• Chemspider ID: 31647
• 维基百科标题: Fluorenylmethyloxycarbonyl_chloride

理论计算性质

• Acid pKa: 17.405373
• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 4.1151657
• LogD (pH = 7.4): 4.1151657
• Log P: 4.1151657
• 摩尔折射率: 71.1382 cm^3
• 极化性: 28.697273 Å^3
• 极化表面积: 26.3 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: dioxane: soluble0.1 g/mL, clear, colorless
• 熔点: 33 - 35°C; 60-64°C; 61-63 °C; 61-64 °C; 62-64 °C; 62-64 °C(lit.); 62-64°C
• 疏水性(logP): 4.081

安全信息

• 保存条件: 2-8°C, Desiccate
• 保存注意事项: Moisture Sensitive; Toxic/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon
• RTECS编号: LQ6250000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); X
• 联合国危险货物编号: 1759; 3261; UN2923
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 2X
• 危险公开号: 20/22-34; 34; R:34; R34
• 安全公开号: 26-36/37/39-45; S:26-27/28-36/37/39-46; S26 S36/37/39 S45
• 欧盟危险货物分类: C10
• 欧盟危险识别号(EUHIN): 8B
• 美国ERG指导号: 154
• TSCA收录: 否
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H331-H314-H318; H314
• GHS警示性声明: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥99.0% (HPLC); 95%; 97%; 98%
• 级别: for HPLC derivatization; purum
• Empirical Formula (Hill Notation): C15H11ClO2

详细说明

MP Biomedicals - 02150200

Base sensitive amino protecting group for solid-phase peptide synthesis.

Sigma Aldrich - F0378

Application
在氨基酸 HPLC 分析中，用于衍生化氨基酸；在固相肽合成中用于制备 N-Fmoc 氨基酸。

Sigma Aldrich - 160512

Application
在氨基酸 HPLC 分析中，用于衍生化氨基酸；在固相肽合成中用于制备 N-Fmoc 氨基酸。
氨基保护试剂，最近用于合成二环脯氨酸类似物。
用于 HLPC 分析的氨基酸衍生化试剂。1N-保护试剂，用于肽2和寡聚核苷酸3的合成。
包装
1, 5, 25 g in glass bottle

Sigma Aldrich - 23186

Application
在氨基酸 HPLC 分析中，用于衍生化氨基酸；在固相肽合成中用于制备 N-Fmoc 氨基酸。
Other Notes
在 HPLC 和荧光检测（吸收：265nm，发射：315nm）中用于胺的柱前衍生化1,2,3；用于毛细管电泳4

Sigma Aldrich - 23185

Application
在氨基酸 HPLC 分析中，用于衍生化氨基酸；在固相肽合成中用于制备 N-Fmoc 氨基酸。
Other Notes
用于引入氨基保护基团 9-芴甲氧羰基 (Fmoc)，Fmoc 对酸和催化氢化反应稳定，但在温和碱性非水解条件下易被裂解1,2；Fmoc 基团可用于保护羟基3；保护核苷酸中的氨基4

参考文献

• Carpino, L.A. and Han, G.Y., J. Org. Chem. , 37 : 3404 (1972).
• Chang, C.D., Waki, M., Ahmad, M., Meienhofer, J., Lundell, E.O. and Haug, J.D., Int. J. Peptide Protein Res. , 15 : 59 (1980).
• 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).