Fluorenylmethyloxycarbonyl chloride

Fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) is a chloroformate ester. It is used to introduce the fluorenylmethyloxycarbonyl protecting group as the Fmoc carbamate.

Fluorenylmethyloxycarbonyl chloride[1]
Ball-and-stick model of the fluorenylmethyloxycarbonyl chloride molecule
Names
Preferred IUPAC name
(9H-Fluoren-9-yl)methyl carbonochloridate
Other names
9-Fluorenylmethyl chloroformate; 9-Fluorenylmethoxycarbonyl chloride; Fmoc-chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.816
EC Number
  • 249-313-6
UNII
  • 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 checkY
    Key: IRXSLJNXXZKURP-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: IRXSLJNXXZKURP-UHFFFAOYAT
  • ClC(=O)OCC3c1ccccc1c2c3cccc2
Properties
C15H11ClO2
Molar mass 258.70 g·mol−1
Melting point 62 to 64 °C (144 to 147 °F; 335 to 337 K)
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

This compound may be prepared by reacting 9-fluorenylmethanol with phosgene:[2]

References
  1. Fmoc chloride at Sigma-Aldrich
  2. Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404. doi:10.1021/jo00795a005.
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