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10926

Sigma-Aldrich

9-Fluorenylmethyl N-hydroxycarbamate

≥99.0%

Synonym(s):

N-(9-Fluorenylmethoxycarbonyl)hydroxylamine, N-Fmoc-hydroxylamine

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About This Item

Empirical Formula (Hill Notation):
C15H13NO3
CAS Number:
190656-01-0
Molecular Weight:
255.27
Beilstein/REAXYS Number:
7712144
MDL number:
MFCD01862911
UNSPSC Code:
12352005
PubChem Substance ID:
57646856

assay

≥99.0%

mp

164.5 °C (lit.)

application(s)

peptide synthesis

SMILES string

ONC(=O)OCC1c2ccccc2-c3ccccc13

InChI

1S/C15H13NO3/c17-15(16-18)19-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14,18H,9H2,(H,16,17)

InChI key

HHNJBGORPSTJDX-UHFFFAOYSA-N

Application

9-Fluorenylmethyl N-hydroxycarbamate (Fmoc-NHOH) can be used as a reactant to prepare:
  • N-Fmoc-aminooxy-2-chlorotrityl polystyrene, a solid-phase resin used to produce hydroxamic acids and peptidyl hydroxamic acids.
  • 9-Fluorenylmethyl nosyloxycarbamate (Fmoc-NHONs) by reacting with nosyl chloride.

Other Notes

Building block for the solid-phase synthesis of (peptide) hydroxamic acids on chlorotrityl resin

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: A facile solid-phase methodology for the synthesis of hydroxamic acids
Mellor SL, et al.
Tetrahedron Letters, 38(18), 3311-3314 (1997)
S.L. Mellor et al.
Tetrahedron Letters, 38, 3311-3311 (1997)
Synthesis of N-protected cyano aziridines
Fioravanti S, et al.
Synlett, 2004(06), 1083-1085 (2004)

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