8.18203
(9-Fluorenylmethyl) chloroformate
for synthesis
别名:
(9-Fluorenylmethyl) chloroformate, Chloroformic acid 9-fluorenylmethyl ester, FMOCCl
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关于此项目
经验公式（希尔记法）:
C15H11ClO2
化学文摘社编号:
分子量:
258.70
UNSPSC Code:
12352108
EC Index Number:
249-313-6
NACRES:
NA.22
MDL number:
Grade:
synthesis grade
Application(s):
peptide synthesis
产品名称
(9-Fluorenylmethyl) chloroformate, for synthesis
SMILES string
ClC(=O)OCC1c2c(cccc2)c3c1cccc3
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
InChI key
IRXSLJNXXZKURP-UHFFFAOYSA-N
grade
synthesis grade
form
powder
dilution
(for synthesis)
mp
60-63 °C
application(s)
peptide synthesis
storage temp.
15-25°C
Quality Level
Application
Recent applications of (9-Fluorenylmethyl) chloroformate include:
- (9-Fluorenylmethyl) chloroformate can be used as a coupling reagent.
- In the synthesis of amino acid esters. Fmoc chloride activates the carboxylic acid group of the amino acid, allowing it to react with an alcohol to form the ester.
- In the preparation of lysogangliosides.
- In the solid-phase peptide synthesis of DOPA-containing peptides.
General description
(9-Fluorenylmethyl) chloroformate, also known as Fmoc chloride, is a highly versatile reagent with varied applications in organic synthesis. It is most frequently used to introduce the base-labile Fmoc-protecting group to amine functionalities, particularly during the production of Fmoc-protected amino acids. Fmoc-chloride has also been used to generate mixed carboxylic and carbonic anhydrides to facilitate amide and ester bond formation. It is soluble in common organic solvents such as dichloromethane, tetrahydrofuran, and dimethylformamide.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
supp_hazards
存储类别
8A - Combustible, corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Synthesis of Reactive Amino Acid Esters by Using 9-Fluorenylmethyl Chloroformate
Yamamoto H and Wu A
Synfacts, 16, 1247-1247 (2020)
Synthesis of peptides containing DOPA (3, 4-dihydroxyphenylalanine)
Sever MJ and Wilker JJ
Tetrahedron, 6139-6146 (2001)
9-Fluorenylmethoxycarbonyl amino-protecting group
Carpino LA and Han GY
The Journal of Organic Chemistry, 37, 3404-3404 (1972)
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