Fluorenylmethyloxycarbonyl chloride

Last updated
Fluorenylmethyloxycarbonyl chloride [1]
Fmoc-2D-skeletal.png
Fluorenylmethyloxycarbonyl-chloride-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 249-313-6
PubChem CID
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 Yes check.svgY
    Key: IRXSLJNXXZKURP-UHFFFAOYSA-N Yes check.svgY
  • 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:
GHS-pictogram-acid.svg
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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Fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) is a chloroformate ester. It is used to introduce the fluorenylmethyloxycarbonyl protecting group as the Fmoc carbamate.

Preparation

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

Preparation of Fmoc-Cl.png

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The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic synthesis.

The molecular formula C15H11ClO2 (molar mass: 258.70 g/mol) may refer to:

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.