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Key Documents

8.18203

Sigma-Aldrich

(9-Fluorenylmethyl) chloroformate

for synthesis

Synonym(s):

(9-Fluorenylmethyl) chloroformate, Chloroformic acid 9-fluorenylmethyl ester, FMOCCl

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About This Item

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

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.

Pictograms

Corrosion

Signal Word

Danger

Hazard 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of peptides containing DOPA (3, 4-dihydroxyphenylalanine)
Sever MJ and Wilker JJ
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9-Fluorenylmethoxycarbonyl amino-protecting group
Carpino LA and Han GY
The Journal of Organic Chemistry, 37, 3404-3404 (1972)

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