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8.18203

(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:
28920-43-6
Molecular Weight:
258.70
UNSPSC Code:
12352108
EC Index Number:
249-313-6
NACRES:
NA.22
MDL number:
MFCD00001138
Grade:
synthesis grade
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grade

synthesis grade

Quality Level

200

form

powder

dilution

(for synthesis)

mp

60-63 °C

application(s)

peptide synthesis

storage temp.

15-25°C

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

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.

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pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH029

Storage Class

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 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)

Global Trade Item Number

SKUGTIN
818203002504022536982083
818203000504022536430096
818203850004027269278595