8.18203
(9-Fluorenylmethyl) chloroformate
for synthesis
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Synonym(s):
(9-Fluorenylmethyl) chloroformate, Chloroformic acid 9-fluorenylmethyl ester, FMOCCl
Empirical Formula (Hill Notation):
C15H11ClO2
CAS Number:
Molecular Weight:
258.70
MDL number:
UNSPSC Code:
12352108
EC Index Number:
249-313-6
NACRES:
NA.22
Recommended Products
Quality Level
form
powder
mp
60-63 °C
application(s)
peptide synthesis
storage temp.
15-25°C
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
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.
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Supplementary Hazards
Storage Class Code
8A - Combustible, corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Find documentation for the products that you have recently purchased in the Document Library.
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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