9-Fluorenylmethyl Chloroformate 9-芴甲基氯甲酸酯

CAS 28920-43-6 MFCD00001138

化学结构图

28920-43-6
SMILES: O=C(Cl)OCC1c2ccccc2-c2ccccc21

化学属性

Mol. FormulaC15H11ClO2
Mol. Weight259
Melting Point63
Density1.288
TSCANo
Stability易吸潮
pH:A

别名和识别编码

Chemical Name9-Fluorenylmethyl Chloroformate
Synonym 9-Fluorenylmethyl chloroformate 9-Fluorenylmethyloxycarbonylchloride 9-芴甲氧羰酰氯,氯甲酸-9-芴甲酯 Chloroformic acid 9-fluorenylmethyl ester 氯甲酸-9-芴基甲酯, 9-芴甲氧羰酰氯 氯甲酸-9-芴基甲酯;9-芴甲氧羰酰氯;氯甲酸-9-芴甲酯;9-氯甲酸芴甲酯;9-芴甲基氯甲酸酯 氯甲酸-9-芴甲酯 芴甲氧羰酰氯
MDL NumberMFCD00001138
PubChem Substance ID34367
Beilstein Registry Number2279177
EC Number249-313-6
CAS Number28920-43-6
Reaxys-RN2279177
Chemical Name Translation9-芴甲基氯甲酸酯
LabNetwork Molecule IDLN00169304
InChIInChI=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
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分类

  • {SNA} Alphabetical, Amino Acid Analysis, Amino Acids, Analytical Reagents, Analytical/Chromatography, Application Spe
  • {SNA} Carbonyl Chlorides, Derivatization Reagents, Derivatization Reagents HPLC, Fluorescence, Fluorescent Labels, Other Fluorescent Labels, UV-VIS, 分析/色谱, 分析试剂, 生化试剂, 荧光探针,标记,粒子和染色剂
  • {SNA} Amine Protection, Chemical Biology, Chemical Synthesis, Others, Peptide Chemistry, Protecting and Derivatizing Reagents, Protection and Derivatization, Synthetic Reagents
  • {SNA} Alphabetical,

产品应用

  • 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。N-保护试剂,用于肽和寡聚核苷酸的合成。

相关文献及参考

  • 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).
  • Merck: 14,10354
  • 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 conditi
  • 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).
  • 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).
  • 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.

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P234 Keep only in original container. 只保留在原来的容器中。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P305+P351+P338
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P390 Absorb spillage to prevent material damage. 吸收溢出物,防止重大损害。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H290 May be corrosive to metals 可能腐蚀金属。
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
RTECSLQ6250000
Signal word Danger
Personal Protective Equipment 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
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
Risk Statements
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
  • R34 Causes burns 会导致灼伤
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Packing GroupII
UN Number 3261
Storage condition Moisture Sensitive 0-10 易潮解,储存温度2-8℃ 0-10°C 储存温度2-8℃,充氩保存
Hazard Codes 8 C
Hazard Class8
TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 170,23,1986

其他信息

  • 室温下长期放置会缓慢分解。易吸潮,水中分解。

系列性分类